Inositol: Difference between revisions
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| IUPACName = ''myo''-Inositol | | IUPACName = ''myo''-Inositol | ||
| SystematicName = (1''R'',2''S'',3''r'',4''R'',5''S'',6''s'')-Cyclohexane-1,2,3,4,5,6-hexol | | SystematicName = (1''R'',2''S'',3''r'',4''R'',5''S'',6''s'')-Cyclohexane-1,2,3,4,5,6-hexol | ||
| OtherNames = ''cis''-1,2,3,5-''trans''-4,6-Cyclohexanehexol<br>Cyclohexanehexol<br>Mouse antialopecia factor<br>Nucite<br>Phaseomannite<br>Phaseomannitol<br>Rat antispectacled eye factor<br>Scyllite <small>(for the isomer ''scyllo''-inositol)</small><br>Vitamin B<sub>8</sub> | | OtherNames = ''cis''-1,2,3,5-''trans''-4,6-Cyclohexanehexol<br />Cyclohexanehexol<br />Mouse antialopecia factor<br />Nucite<br />Phaseomannite<br />Phaseomannitol<br />Rat antispectacled eye factor<br />Scyllite <small>(for the isomer ''scyllo''-inositol)</small><br />Vitamin B<sub>8</sub> | ||
|Section1={{Chembox Identifiers | |Section1={{Chembox Identifiers | ||
| IUPHAR_ligand = 4495 | | IUPHAR_ligand = 4495 | ||
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}} | }} | ||
| Section4 = {{Chembox Thermochemistry | | Section4 = {{Chembox Thermochemistry | ||
| Thermochemistry_ref =<ref>{{cite journal |last1=Knyazev |first1=A.V. |last2= | | Thermochemistry_ref =<ref>{{cite journal |last1=Knyazev |first1=A.V. |last2=Emelʹyanenko |first2=V.N. |last3=Shipilova |first3=A.S. |last4=Zaitsau |first4=D.H. |last5=Lelet |first5=M.I. |last6=Knyazeva |first6=S.S. |last7=Gusarova |first7=E.V. |last8=Varfolomeev |first8=M.A. |date=2018 |title=Thermodynamic properties of myo-inositol |journal=The Journal of Chemical Thermodynamics |volume=116 |pages=76–84 |issn=0021-9614 |doi=10.1016/j.jct.2017.08.028 |bibcode=2018JChTh.116...76K |url=https://www.sciencedirect.com/science/article/abs/pii/S0021961417303075|url-access=subscription }}</ref> | ||
| DeltaGf = | | DeltaGf = | ||
| DeltaHc = −2747 kJ/mol | | DeltaHc = −2747 kJ/mol | ||
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}} | }} | ||
In [[biochemistry]], [[medicine]], and related sciences, '''inositol''' generally refers to '''''myo''-inositol''' (formerly '''''meso''-inositol'''), the most important [[stereoisomer]] of the [[chemical compound]] [[cyclohexane-1,2,3,4,5,6-hexol]]. Its [[elemental formula|formula]] is {{chem2|C6H12O6}}; the molecule has a ring of six [[carbon]] atoms, each with a [[hydrogen]] atom and a [[ | In [[biochemistry]], [[medicine]], and related sciences, '''inositol''' generally refers to '''''myo''-inositol''' (formerly '''''meso''-inositol'''), the most important [[stereoisomer]] of the [[chemical compound]] [[cyclohexane-1,2,3,4,5,6-hexol]]. Its [[elemental formula|formula]] is {{chem2|C6H12O6}}; the molecule has a ring of six [[carbon]] atoms, each with a [[hydrogen]] atom and a [[hydroxy group]] (–OH). In ''myo''-inositol, two of the hydroxyls, neither adjacent nor opposite, lie above the respective hydrogens relative to the mean plane of the ring. | ||
The compound is a [[carbohydrate]], specifically a [[sugar alcohol]] (as distinct from [[ | The compound is a [[carbohydrate]], specifically a [[sugar alcohol]] (as distinct from [[simple sugar]]s like [[glucose]]) with half the [[sweetness]] of [[sucrose]] (table sugar). It is one of the most ancient components of living beings with multiple functions in [[eukaryote]]s, including structural lipids and [[secondary messenger]]s.<ref name=liyu2021/> A human kidney makes about two grams per day from [[glucose]], but other tissues synthesize it too. The highest concentration is in the brain, where it plays an important role in making other [[neurotransmitter]]s and some [[steroid hormone]]s bind to their receptors.<ref>{{cite journal |last1=Croze |first1=M. L. |last2=Soulage |first2=C. O. |title=Potential role and therapeutic interests of ''myo''-inositol in metabolic diseases |journal=Biochimie |volume=95 |issue=10 |pages=1811–1827 |date=October 2013 |pmid=23764390 |doi=10.1016/j.biochi.2013.05.011}}</ref> In other tissues, it mediates cell signal transduction in response to a variety of [[hormone]]s, [[neurotransmitter]]s, and growth factors and participates in [[osmoregulation]].<ref name="parthasarthy">{{cite book |last1=Parthasarathy |first1=L. K. |last2=Seelan |first2=R. S. |last3=Tobias |first3=C. |last4=Casanova |first4=M. F. |last5=Parthasarathy |first5=R. N. |title=Mammalian inositol 3-phosphate synthase: its role in the biosynthesis of brain inositol and its clinical use as a psychoactive agent |volume=39 |pages=293–314 |year=2006 |isbn=978-0-387-27599-4 |series=Subcellular Biochemistry |pmid=17121280 |doi=10.1007/0-387-27600-9_12}}</ref> In most mammalian cells the concentrations of ''myo''-inositol are 5 to 500 times greater inside cells than outside them.<ref name="pmid33755975"/> | ||
A 2023 meta-analysis found that inositol is a safe and effective treatment in the management of [[polycystic ovary syndrome]] (PCOS).<ref name="pcos2023"/> However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS.<ref name=showell2018>{{cite journal |year=2018 |last1=Showell |first1=M. G. |last2=Mackenzie-Proctor |first2=R. |last3=Jordan |first3=V. |last4=Hodgson |first4=R. |last5=Farquhar |first5=C. |title=Inositol for subfertile women with polycystic ovary syndrome |journal=The Cochrane Database of Systematic Reviews |volume=2018 |issue=12 | | A 2023 meta-analysis found that inositol is a safe and effective treatment in the management of [[polycystic ovary syndrome]] (PCOS).<ref name="pcos2023"/> However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS.<ref name=showell2018>{{cite journal |year=2018 |last1=Showell |first1=M. G. |last2=Mackenzie-Proctor |first2=R. |last3=Jordan |first3=V. |last4=Hodgson |first4=R. |last5=Farquhar |first5=C. |title=Inositol for subfertile women with polycystic ovary syndrome |journal=The Cochrane Database of Systematic Reviews |volume=2018 |issue=12 |article-number=CD012378 |pmid=30570133 |doi=10.1002/14651858.CD012378.pub2 |pmc=6516980}}</ref> | ||
The other naturally occurring stereoisomers of cyclohexane-1,2,3,4,5,6-hexol are [[scyllo-inositol|''scyllo'']]-, [[muco-inositol|''muco'']]-, [[1D-chiro-inositol|{{small|D}}-''chiro'']]-, [[L-chiro-inositol|{{small|L}}-''chiro'']]-, and [[neo-inositol|''neo''-inositol]], although they occur in minimal quantities compared to ''myo''-inositol. The other possible isomers are [[allo-inositol|''allo'']]-, [[epi-inositol|''epi'']]-, and [[cis-inositol|''cis''-inositol]]. | The other naturally occurring stereoisomers of cyclohexane-1,2,3,4,5,6-hexol are [[scyllo-inositol|''scyllo'']]-, [[muco-inositol|''muco'']]-, [[1D-chiro-inositol|{{small|D}}-''chiro'']]-, [[L-chiro-inositol|{{small|L}}-''chiro'']]-, and [[neo-inositol|''neo''-inositol]], although they occur in minimal quantities compared to ''myo''-inositol. The other possible isomers are [[allo-inositol|''allo'']]-, [[epi-inositol|''epi'']]-, and [[cis-inositol|''cis''-inositol]]. | ||
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''myo''-Inositol is a [[meso compound]], meaning it is [[optical rotation|optically inactive]] because it has a [[reflection symmetry|plane of symmetry]].<ref name=maju2006/> It is a white crystalline powder, relatively stable in the air. It is highly soluble in water, slightly soluble in [[glacial acetic acid]], [[ethanol]], [[glycol]], and [[glycerin]], but insoluble in [[chloroform]] and [[ether]].<ref name=liyu2021/> | ''myo''-Inositol is a [[meso compound]], meaning it is [[optical rotation|optically inactive]] because it has a [[reflection symmetry|plane of symmetry]].<ref name=maju2006/> It is a white crystalline powder, relatively stable in the air. It is highly soluble in water, slightly soluble in [[glacial acetic acid]], [[ethanol]], [[glycol]], and [[glycerin]], but insoluble in [[chloroform]] and [[ether]].<ref name=liyu2021/> | ||
In its most stable [[conformational isomerism|conformation]], the ''myo''-inositol isomer assumes the [[cyclohexane conformation|chair conformation]], which moves the maximum number of hydroxyls to the equatorial position, where they are farthest apart from each other. In this conformation, the natural ''myo'' isomer has a structure in which five of the six [[hydroxyl]]s (the first, third, fourth, fifth, and sixth) are [[equatorial bond|equatorial]], whereas the second hydroxyl group is [[axis of rotation|axial]].<ref>{{cite book |title=Basic Neurochemistry: Molecular, Cellular and Medical Aspects |last1=Brady |first1=S. |last2=Siegel |first2=G. |last3=Albers |first3=R. W. |last4=Price |first4=D. |date=2005 |publisher=Academic Press |isbn= | In its most stable [[conformational isomerism|conformation]], the ''myo''-inositol isomer assumes the [[cyclohexane conformation|chair conformation]], which moves the maximum number of hydroxyls to the equatorial position, where they are farthest apart from each other. In this conformation, the natural ''myo'' isomer has a structure in which five of the six [[hydroxyl]]s (the first, third, fourth, fifth, and sixth) are [[equatorial bond|equatorial]], whereas the second hydroxyl group is [[axis of rotation|axial]].<ref>{{cite book |title=Basic Neurochemistry: Molecular, Cellular and Medical Aspects |last1=Brady |first1=S. |last2=Siegel |first2=G. |last3=Albers |first3=R. W. |last4=Price |first4=D. |date=2005 |publisher=Academic Press |isbn=978-0-08-047207-2 |page=348 |language=en |url=https://books.google.com/books?id=Af0IyHtGCMUC&pg=PA348}}</ref> | ||
==Physiological roles== | ==Physiological roles== | ||
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===Phytic acid in plants=== | ===Phytic acid in plants=== | ||
[[File:Phytic acid.svg|alt=2D-structure of phytic acid|thumb|Inositolhexaphosphate, or phytic acid]] | [[File:Phytic acid.svg|alt=2D-structure of phytic acid|thumb|Inositolhexaphosphate, or phytic acid]] | ||
Inositol hexaphosphate, also called [[phytic acid]] or IP6, is a [[phytochemical]] and the principal storage form of [[phosphorus]] in many [[plant]] [[biological tissue|tissues]], especially [[bran]] and [[seed]].<ref name="phytochemicals">{{cite web |title=Phytic acid |website=phytochemicals.info |url=http://www.phytochemicals.info/phytochemicals/phytic-acid.php |access-date=2018-05-02 |url-status=usurped |archive-url=https://web.archive.org/web/20180307183152/http://www.phytochemicals.info/phytochemicals/phytic-acid.php |archive-date=7 March 2018}}</ref> Phosphorus and inositol in phytate form are not generally [[bioavailability|bioavailable]] to non-[[ruminant]] animals because these animals lack the digestive [[enzyme]] [[phytase]] required to remove the phosphate groups. Ruminants readily digest phytate because of the phytase produced by microorganisms in the [[rumen]].<ref name="CAST">{{cite journal |last1=Klopfenstein |first1=T. J. |last2=Angel |first2=R. |last3=Cromwell |first3=G. |last4=Erickson |first4=G. E. |last5=Fox |first5=D. G. |last6=Parsons |first6=C. |last7=Satter |first7=L. D. |last8=Sutton |first8=A. L. |last9=Baker |first9=D. H. |date=July 2002 |title=Animal diet modification to decrease the potential for nitrogen and phosphorus pollution |journal=Council for Agricultural Science and Technology |volume=21 |url=https://digitalcommons.unl.edu/animalscifacpub/518/ |url-status=live |archive-url=https://web.archive.org/web/20110611164403/http://digitalcommons.unl.edu/animalscifacpub/518/ |archive-date=2011-06-11}}</ref> Moreover, phytic acid also [[chelation|chelates]] important minerals such as [[calcium]], [[magnesium]], [[iron]], and [[zinc]], making them unabsorbable, and contributing to mineral deficiencies in people whose diets rely highly on bran and seeds for their mineral intake, such as occurs in [[developing country|developing countries]].<ref>{{cite journal |last=Hurrell |first=R. F. |title=Influence of vegetable protein sources on trace element and mineral bioavailability |journal=The Journal of Nutrition |volume=133 |issue=9 |pages=2973S–2977S |date=September 2003 |pmid=12949395 |doi=10.1093/jn/133.9.2973S |doi-access=free}}</ref><ref>{{cite book |chapter=Phytates |title=Toxicants Occurring Naturally in Foods |author=Committee on Food Protection |author2=Food and Nutrition Board |author3=National Research Council |publisher=National Academy of Sciences |year=1973 |isbn=978-0-309-02117-3 |pages=[https://archive.org/details/toxicantsoccurri0000unse/page/363 363–371] |chapter-url=https://books.google.com/books?id=lIsrAAAAYAAJ&pg=PA363 |url=https://archive.org/details/toxicantsoccurri0000unse/page/363}}</ref> | Inositol hexaphosphate, also called [[phytic acid]] or IP6, is a [[phytochemical]] and the principal storage form of [[phosphorus]] in many [[plant]] [[biological tissue|tissues]], especially [[bran]] and [[seed]].<ref name="phytochemicals">{{cite web |title=Phytic acid |website=phytochemicals.info |url=http://www.phytochemicals.info/phytochemicals/phytic-acid.php |access-date=2018-05-02 |url-status=usurped |archive-url=https://web.archive.org/web/20180307183152/http://www.phytochemicals.info/phytochemicals/phytic-acid.php |archive-date=7 March 2018}}</ref> Phosphorus and inositol in phytate form are not generally [[bioavailability|bioavailable]] to non-[[ruminant]] animals because these animals lack the digestive [[enzyme]] [[phytase]] required to remove the phosphate groups. Ruminants readily digest phytate because of the phytase produced by microorganisms in the [[rumen]].<ref name="CAST">{{cite journal |last1=Klopfenstein |first1=T. J. |last2=Angel |first2=R. |last3=Cromwell |first3=G. |last4=Erickson |first4=G. E. |last5=Fox |first5=D. G. |last6=Parsons |first6=C. |last7=Satter |first7=L. D. |last8=Sutton |first8=A. L. |last9=Baker |first9=D. H. |date=July 2002 |title=Animal diet modification to decrease the potential for nitrogen and phosphorus pollution |journal=Council for Agricultural Science and Technology |volume=21 |url=https://digitalcommons.unl.edu/animalscifacpub/518/ |url-status=live |archive-url=https://web.archive.org/web/20110611164403/http://digitalcommons.unl.edu/animalscifacpub/518/ |archive-date=2011-06-11}}</ref> Moreover, phytic acid also [[chelation|chelates]] important minerals such as [[calcium]], [[magnesium]], [[iron]], and [[zinc]], making them unabsorbable, and contributing to mineral deficiencies in people whose diets rely highly on bran and seeds for their mineral intake, such as occurs in [[developing country|developing countries]].<ref>{{cite journal |last=Hurrell |first=R. F. |title=Influence of vegetable protein sources on trace element and mineral bioavailability |journal=The Journal of Nutrition |volume=133 |issue=9 |pages=2973S–2977S |date=September 2003 |pmid=12949395 |doi=10.1093/jn/133.9.2973S |doi-access=free}}</ref><ref>{{cite book |chapter=Phytates |title=Toxicants Occurring Naturally in Foods |author=Committee on Food Protection |author2=Food and Nutrition Board |author3=National Research Council |publisher=National Academy of Sciences |year=1973 |isbn=978-0-309-02117-3 |pages=[https://archive.org/details/toxicantsoccurri0000unse/page/363 363–371] |chapter-url=https://books.google.com/books?id=lIsrAAAAYAAJ&pg=PA363 |url=https://archive.org/details/toxicantsoccurri0000unse/page/363}}</ref> Because of this, phytic acid is considered as an antinutrient. | ||
Inositol penta- (IP5), tetra- (IP4), and triphosphate (IP3) are also called "phytates". | Inositol penta- (IP5), tetra- (IP4), and triphosphate (IP3) are also called "phytates". | ||
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* Breakdown of [[fat]]s<ref name="pmid3103610">{{cite journal |last1=Rapiejko |first1=P. J. |last2=Northup |first2=J. K. |last3=Evans |first3=T. |last4=Brown |first4=J. E. |last5=Malbon |first5=C. C. |title=G-proteins of fat-cells. Role in hormonal regulation of intracellular inositol 1,4,5-trisphosphate |journal=The Biochemical Journal |volume=240 |issue=1 |pages=35–40 |date=November 1986 |pmid=3103610 |doi=10.1042/bj2400035 |pmc=1147372}}</ref> | * Breakdown of [[fat]]s<ref name="pmid3103610">{{cite journal |last1=Rapiejko |first1=P. J. |last2=Northup |first2=J. K. |last3=Evans |first3=T. |last4=Brown |first4=J. E. |last5=Malbon |first5=C. C. |title=G-proteins of fat-cells. Role in hormonal regulation of intracellular inositol 1,4,5-trisphosphate |journal=The Biochemical Journal |volume=240 |issue=1 |pages=35–40 |date=November 1986 |pmid=3103610 |doi=10.1042/bj2400035 |pmc=1147372}}</ref> | ||
* [[Gene expression]]<ref>{{cite journal |last1=Shen |first1=X. |last2=Xiao |first2=H. |last3=Ranallo |first3=R. |last4=Wu |first4=W.-H. |last5=Wu |first5=C. |title=Modulation of ATP-dependent chromatin-remodeling complexes by inositol polyphosphates |journal=Science |volume=299 |issue=5603 |pages=112–114 |date=January 2003 |bibcode=2003Sci...299..112S |pmid=12434013 |doi=10.1126/science.1078068 |doi-access=free |s2cid=8381889 |url=https://zenodo.org/record/1230822}}</ref><ref>{{cite journal |last1=Steger |first1=D. J. |last2=Haswell |first2=E. S. |last3=Miller |first3=A. L. |last4=Wente |first4=S. R. |last5=O'Shea |first5=E. K. |title=Regulation of chromatin remodeling by inositol polyphosphates |journal=Science |volume=299 |issue=5603 |pages=114–116 |date=January 2003 |bibcode=2003Sci...299..114S |pmid=12434012 |doi=10.1126/science.1078062 |pmc=1458531}}</ref> | * [[Gene expression]]<ref>{{cite journal |last1=Shen |first1=X. |last2=Xiao |first2=H. |last3=Ranallo |first3=R. |last4=Wu |first4=W.-H. |last5=Wu |first5=C. |title=Modulation of ATP-dependent chromatin-remodeling complexes by inositol polyphosphates |journal=Science |volume=299 |issue=5603 |pages=112–114 |date=January 2003 |bibcode=2003Sci...299..112S |pmid=12434013 |doi=10.1126/science.1078068 |doi-access=free |s2cid=8381889 |url=https://zenodo.org/record/1230822}}</ref><ref>{{cite journal |last1=Steger |first1=D. J. |last2=Haswell |first2=E. S. |last3=Miller |first3=A. L. |last4=Wente |first4=S. R. |last5=O'Shea |first5=E. K. |title=Regulation of chromatin remodeling by inositol polyphosphates |journal=Science |volume=299 |issue=5603 |pages=114–116 |date=January 2003 |bibcode=2003Sci...299..114S |pmid=12434012 |doi=10.1126/science.1078062 |pmc=1458531}}</ref> | ||
In one important family of pathways, [[phosphatidylinositol 4,5-bisphosphate]] (PIP<sub>2</sub>) is stored in cellular membranes until it is released by any of a number of signalling proteins and transformed into various secondary messengers, for example [[diglyceride|diacylglycerol]] and [[inositol trisphosphate]].<ref>{{cite book |title=Biochemistry |last1=Mathews |first1=C. K. |date=2000 |publisher=Benjamin Cummings |last2=Van Holde |first2=K. E. |last3=Ahern |first3=K. G. |isbn=978- | In one important family of pathways, [[phosphatidylinositol 4,5-bisphosphate]] (PIP<sub>2</sub>) is stored in cellular membranes until it is released by any of a number of signalling proteins and transformed into various secondary messengers, for example [[diglyceride|diacylglycerol]] and [[inositol trisphosphate]].<ref>{{cite book |title=Biochemistry |last1=Mathews |first1=C. K. |date=2000 |publisher=Benjamin Cummings |last2=Van Holde |first2=K. E. |last3=Ahern |first3=K. G. |isbn=978-0-8053-3066-3 |edition=3rd |location=San Francisco, CA |page=855 |oclc=42290721}}</ref> | ||
'''myo''-Inositol has very low toxicity, with a reported [[lethal dose|LD<sub>50</sub>]] 10,000 mg/kg body weight (oral) in rats.<ref name=liyu2021/> | '''myo''-Inositol has very low toxicity, with a reported [[lethal dose|LD<sub>50</sub>]] 10,000 mg/kg body weight (oral) in rats.<ref name=liyu2021/> | ||
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===Explosives industry=== | ===Explosives industry=== | ||
At the 1936 meeting of the [[American Chemical Society]], professor [[Edward Bartow]] of the [[University of Iowa]] presented a commercially viable means of extracting large amounts of inositol from the phytic acid naturally present in waste corn. As a possible use for the chemical, he suggested 'inositol nitrate' as a more stable alternative to [[nitroglycerin]].<ref>{{cite news |last=Laurence |first=W. L. |title=Corn by-product yields explosive |newspaper=The New York Times |date=April 17, 1936 |page=7 |url=https://www.nytimes.com/1936/04/17/archives/corn-byproduct-yields-explosive-new-process-utilizes-wastage-in.html |archive-url=https://web.archive.org/web/20130512022104/http://select.nytimes.com/gst/abstract.html?res=F50B15F9395D13728DDDAE0994DC405B868FF1D3&scp=1 |archive-date=2013-05-12}}</ref> Today, inositol nitrate is used to gelatinize [[nitrocellulose]] in many modern explosives and solid rocket propellants.<ref>{{cite book |last=Ledgard |first=J. |title=The Preparatory Manual of Explosives |date=2007 |page=366 |publisher=Ledgard |isbn= | At the 1936 meeting of the [[American Chemical Society]], professor [[Edward Bartow]] of the [[University of Iowa]] presented a commercially viable means of extracting large amounts of inositol from the phytic acid naturally present in waste corn. As a possible use for the chemical, he suggested 'inositol nitrate' as a more stable alternative to [[nitroglycerin]].<ref>{{cite news |last=Laurence |first=W. L. |title=Corn by-product yields explosive |newspaper=The New York Times |date=April 17, 1936 |page=7 |url=https://www.nytimes.com/1936/04/17/archives/corn-byproduct-yields-explosive-new-process-utilizes-wastage-in.html |archive-url=https://web.archive.org/web/20130512022104/http://select.nytimes.com/gst/abstract.html?res=F50B15F9395D13728DDDAE0994DC405B868FF1D3&scp=1 |archive-date=2013-05-12}}</ref> Today, inositol nitrate is used to gelatinize [[nitrocellulose]] in many modern explosives and solid rocket propellants.<ref>{{cite book |last=Ledgard |first=J. |title=The Preparatory Manual of Explosives |date=2007 |page=366 |publisher=Ledgard |isbn=978-0-615-14290-6 |url=https://books.google.com/books?id=J55D3HcgPuoC&q=Inositol%20explosive&pg=PA366}}</ref> | ||
===Road salt=== | ===Road salt=== | ||
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===Other illnesses=== | ===Other illnesses=== | ||
D-''chiro''-inositol is an important messenger molecule in insulin signaling.<ref name="pmid29793496">{{cite journal |vauthors=Tabrizi R, Ostadmohammadi V, Asemi Z |title=The effects of inositol supplementation on lipid profiles among patients with metabolic diseases: a systematic review and meta-analysis of randomized controlled trials |journal=[[Q15756695|Lipids in Health and Disease]] |volume=17 |issue=1 | | D-''chiro''-inositol is an important messenger molecule in insulin signaling.<ref name="pmid29793496">{{cite journal |vauthors=Tabrizi R, Ostadmohammadi V, Asemi Z |title=The effects of inositol supplementation on lipid profiles among patients with metabolic diseases: a systematic review and meta-analysis of randomized controlled trials |journal=[[Q15756695|Lipids in Health and Disease]] |volume=17 |issue=1 |article-number=123 |year=2018 |pmid=29793496 |doi=10.1186/s12944-018-0779-4 |doi-access=free |pmc=5968598}}</ref> Inositol supplementation has been shown to significantly decrease [[triglyceride]]s and [[low-density lipoprotein|LDL cholesterol]] in patients with [[metabolic syndrome|metabolic diseases]].<ref name="pmid29793496"/> | ||
''myo''-Inositol is important for [[thyroid hormones|thyroid hormone]] synthesis.<ref name="pmid34040582"/> Depletion of ''myo''-inositol may predispose to development of [[hypothyroidism]].<ref name="pmid34040582"/> Patients with hypothyroidism have a higher demand for ''myo''-inositol than healthy subjects.<ref name="pmid34040582">{{cite journal |vauthors=Benvenga S, Nordio M, Laganà AS, Unfer V |title=The Role of Inositol in Thyroid Physiology and in Subclinical Hypothyroidism Management |journal=[[Frontiers in Endocrinology]] |volume=12 | | ''myo''-Inositol is important for [[thyroid hormones|thyroid hormone]] synthesis.<ref name="pmid34040582"/> Depletion of ''myo''-inositol may predispose to development of [[hypothyroidism]].<ref name="pmid34040582"/> Patients with hypothyroidism have a higher demand for ''myo''-inositol than healthy subjects.<ref name="pmid34040582">{{cite journal |vauthors=Benvenga S, Nordio M, Laganà AS, Unfer V |title=The Role of Inositol in Thyroid Physiology and in Subclinical Hypothyroidism Management |journal=[[Frontiers in Endocrinology]] |volume=12 |article-number=662582 |year=2021 |pmid=34040582 |doi=10.3389/fendo.2021.662582 |doi-access=free |pmc=8143049}}</ref> | ||
Inositol should not be routinely implemented for the management of preterm babies who have or are at a risk of [[infant respiratory distress syndrome]] (RDS).<ref>{{cite journal |last1=Howlett |first1=Alexandra |last2=Ohlsson |first2=Arne |last3=Plakkal |first3=Nishad |date=8 July 2019 |title=Inositol in preterm infants at risk for or having respiratory distress syndrome |journal=The Cochrane Database of Systematic Reviews |volume=7 |issue=7 | | Inositol should not be routinely implemented for the management of preterm babies who have or are at a risk of [[infant respiratory distress syndrome]] (RDS).<ref>{{cite journal |last1=Howlett |first1=Alexandra |last2=Ohlsson |first2=Arne |last3=Plakkal |first3=Nishad |date=8 July 2019 |title=Inositol in preterm infants at risk for or having respiratory distress syndrome |journal=The Cochrane Database of Systematic Reviews |volume=7 |issue=7 |article-number=CD000366 |issn=1469-493X |pmid=31283839 |doi=10.1002/14651858.CD000366.pub4 |pmc=6613728}}</ref> ''Myo''-inositol helps prevent [[neural tube defect]]s with particular efficacy in combination with [[folic acid]].<ref>{{cite journal |last1=Cavalli |first1=P. |last2=Ronda |first2=E. |title=Myoinositol: the bridge (PONTI) to reach a healthy pregnancy |journal=International Journal of Endocrinology |volume=2017 |article-number=5846286 |date=2017 |pmid=28243254 |doi=10.1155/2017/5846286 |doi-access=free |pmc=5274721}}</ref> | ||
Inositol is considered a safe and effective treatment for [[polycystic ovary syndrome]] (PCOS).<ref name="pcos2023">{{cite journal |title=Inositol is an effective and safe treatment in polycystic ovary syndrome: A systematic review and meta-analysis of randomized controlled trials |date=2023 |last1=Greff |first1=Dorina |last2=Juhász |first2=Anna E. |last3=Váncsa |first3=Szilárd |last4=Váradi |first4=Alex |last5=Sipos |first5=Zoltán |last6=Szinte |first6=Julia |last7=Park |first7=Sunjune |last8=Hegyi |first8=Péter |last9=Nyirády |first9=Péter |last10=Ács |first10=Nándor |last11=Várbíró |first11=Szabolcs |last12=Horváth |first12=Eszter M. |journal=Reproductive Biology and Endocrinology |volume=21 |issue=1 |page=10 |pmid=36703143 |doi=10.1186/s12958-023-01055-z |doi-access=free |pmc=9878965}}</ref> It works by increasing insulin sensitivity, which helps to improve ovarian function and reduce [[hyperandrogenism]].<ref>{{cite journal |last1=Monastra |first1=G. |last2=Unfer |first2=V. |last3=Harrath |first3=A. H. |last4=Bizzarri |first4=M. |title=Combining treatment with ''myo''-inositol and D-''chiro''-inositol (40:1) is effective in restoring ovary function and metabolic balance in PCOS patients |journal=Gynecological Endocrinology |volume=33 |issue=1 |pages=1–9 |date=January 2017 |pmid=27898267 |doi=10.1080/09513590.2016.1247797 |hdl=11573/944617 |s2cid=24836559}}</ref> It is also shown to reduce the risk of [[metabolic disorder|metabolic disease]] in women with PCOS.<ref>{{cite journal |last1=Nordio |first1=M. |last2=Proietti |first2=E. |title=The combined therapy with ''myo''-inositol and D-''chiro''-inositol reduces the risk of metabolic disease in PCOS overweight patients compared to ''myo''-inositol supplementation alone |journal=European Review for Medical and Pharmacological Sciences |volume=16 |issue=5 |pages=575–581 |date=May 2012 |pmid=22774396}}</ref> In addition, thanks to its role as FSH second messenger, ''myo''-inositol is effective in restoring FSH/LH ratio and menstrual cycle regularization.<ref>{{cite journal |last1=Unfer |first1=V. |display-authors=etal |title=Effects of ''myo''-inositol in women with PCOS: a systematic review of randomized controlled trials |journal=Gynecological Endocrinology |volume=28 |issue=7 |pages=509–15 |date=2012 |pmid=22296306 |doi=10.3109/09513590.2011.650660 |s2cid=24582338}}</ref> ''myo''-Inositol's role as FSH second messenger leads to a correct ovarian follicle maturation and consequently to a higher oocyte quality. Improving the oocyte quality in both women with or without PCOS, ''myo''-inositol can be considered as a possible approach for increasing the chance of success in assisted reproductive technologies.<ref>{{cite journal |last1=Ciotta |first1=L. |display-authors=etal |title=Effects of ''myo''-inositol supplementation on oocyte's quality in PCOS patients: a double blind trial |journal=European Review for Medical and Pharmacological Sciences |volume=15 |issue=5 |pages=509–14 |date=2011 |pmid=21744744}}</ref><ref>{{cite journal |last1=Papaleo |first1=E. |display-authors=etal |title=Contribution of ''myo''-inositol to reproduction |journal=European Journal of Obstetrics & Gynecology and Reproductive Biology |volume=147 |issue=2 |pages=120–3 |date=2009 |pmid=19800728 |doi=10.1016/j.ejogrb.2009.09.008}}</ref> In contrast, {{small|D}}-''chiro''-inositol can impair oocyte quality in a dose-dependent manner.<ref>{{cite journal |last1=Isabella |first1=R. |last2=Raffone |first2=E. |title=Does ovary need D-''chiro''-inositol? |journal=Journal of Ovarian Research |volume=5 |issue=1 |date=2012 |page=14 |pmid=22587479 |doi=10.1186/1757-2215-5-14 |doi-access=free |pmc=3447676}}{{Expression of Concern|doi=10.1186/s13048-018-0431-y | Inositol is considered a safe and effective treatment for [[polycystic ovary syndrome]] (PCOS).<ref name="pcos2023">{{cite journal |title=Inositol is an effective and safe treatment in polycystic ovary syndrome: A systematic review and meta-analysis of randomized controlled trials |date=2023 |last1=Greff |first1=Dorina |last2=Juhász |first2=Anna E. |last3=Váncsa |first3=Szilárd |last4=Váradi |first4=Alex |last5=Sipos |first5=Zoltán |last6=Szinte |first6=Julia |last7=Park |first7=Sunjune |last8=Hegyi |first8=Péter |last9=Nyirády |first9=Péter |last10=Ács |first10=Nándor |last11=Várbíró |first11=Szabolcs |last12=Horváth |first12=Eszter M. |journal=Reproductive Biology and Endocrinology |volume=21 |issue=1 |page=10 |pmid=36703143 |doi=10.1186/s12958-023-01055-z |doi-access=free |pmc=9878965}}</ref> It works by increasing insulin sensitivity, which helps to improve ovarian function and reduce [[hyperandrogenism]].<ref>{{cite journal |last1=Monastra |first1=G. |last2=Unfer |first2=V. |last3=Harrath |first3=A. H. |last4=Bizzarri |first4=M. |title=Combining treatment with ''myo''-inositol and D-''chiro''-inositol (40:1) is effective in restoring ovary function and metabolic balance in PCOS patients |journal=Gynecological Endocrinology |volume=33 |issue=1 |pages=1–9 |date=January 2017 |pmid=27898267 |doi=10.1080/09513590.2016.1247797 |hdl=11573/944617 |s2cid=24836559}}</ref> It is also shown to reduce the risk of [[metabolic disorder|metabolic disease]] in women with PCOS.<ref>{{cite journal |last1=Nordio |first1=M. |last2=Proietti |first2=E. |title=The combined therapy with ''myo''-inositol and D-''chiro''-inositol reduces the risk of metabolic disease in PCOS overweight patients compared to ''myo''-inositol supplementation alone |journal=European Review for Medical and Pharmacological Sciences |volume=16 |issue=5 |pages=575–581 |date=May 2012 |pmid=22774396}}</ref> In addition, thanks to its role as FSH second messenger, ''myo''-inositol is effective in restoring FSH/LH ratio and menstrual cycle regularization.<ref>{{cite journal |last1=Unfer |first1=V. |display-authors=etal |title=Effects of ''myo''-inositol in women with PCOS: a systematic review of randomized controlled trials |journal=Gynecological Endocrinology |volume=28 |issue=7 |pages=509–15 |date=2012 |pmid=22296306 |doi=10.3109/09513590.2011.650660 |hdl=11380/744390 |s2cid=24582338}}</ref> ''myo''-Inositol's role as FSH second messenger leads to a correct ovarian follicle maturation and consequently to a higher oocyte quality. Improving the oocyte quality in both women with or without PCOS, ''myo''-inositol can be considered as a possible approach for increasing the chance of success in assisted reproductive technologies.<ref>{{cite journal |last1=Ciotta |first1=L. |display-authors=etal |title=Effects of ''myo''-inositol supplementation on oocyte's quality in PCOS patients: a double blind trial |journal=European Review for Medical and Pharmacological Sciences |volume=15 |issue=5 |pages=509–14 |date=2011 |pmid=21744744}}</ref><ref>{{cite journal |last1=Papaleo |first1=E. |display-authors=etal |title=Contribution of ''myo''-inositol to reproduction |journal=European Journal of Obstetrics & Gynecology and Reproductive Biology |volume=147 |issue=2 |pages=120–3 |date=2009 |pmid=19800728 |doi=10.1016/j.ejogrb.2009.09.008}}</ref> In contrast, {{small|D}}-''chiro''-inositol can impair oocyte quality in a dose-dependent manner.<ref>{{cite journal |last1=Isabella |first1=R. |last2=Raffone |first2=E. |title=Does ovary need D-''chiro''-inositol? |journal=Journal of Ovarian Research |volume=5 |issue=1 |date=2012 |page=14 |pmid=22587479 |doi=10.1186/1757-2215-5-14 |doi-access=free |pmc=3447676}}{{Expression of Concern|doi=10.1186/s13048-018-0431-y|pmid=29976256|http://retractionwatch.com/2018/07/23/journal-flags-fertility-paper-after-company-wins-court-order/ ''Retraction Watch''|doi-access=free}}</ref> The high level of DCI seems to be related to elevated insulin levels retrieved in about 70% of PCOS women.<ref>{{cite journal |last=Moghetti |first=P. |title=Insulin resistance and polycystic ovary syndrome |journal=Current Pharmaceutical Design |date=2016 |volume=22 |issue=36 |pages=5526–5534 |pmid=27510482 |doi=10.2174/1381612822666160720155855}}</ref> In this regard, insulin stimulates the irreversible conversion of ''myo''-inositol to {{small|D}}-''chiro''-inositol causing a drastic reduction of ''myo''-inositol. ''myo''-Inositol depletion is particularly damaging to ovarian follicles because it is involved in FSH signaling, which is impaired due to ''myo''-inositol depletion.<ref name="carlomagno"/> Recent evidence reports a faster improvement of the metabolic and hormonal parameters when these two isomers are administered in their physiological ratio. The plasmatic ratio of ''myo''-inositol and {{small|D}}-''chiro''-inositol in healthy subjects is 40:1 of ''myo''- and {{small|D}}-''chiro''-inositol respectively.<ref>{{cite journal |last1=Facchinetti |first1=F. |display-authors=etal |title=Results from the International Consensus Conference on ''myo''-Inositol and D-''chiro''-Inositol in Obstetrics and Gynecology: the link between metabolic syndrome and PCOS |journal=European Journal of Obstetrics & Gynecology and Reproductive Biology |volume=195 |pages=72–6 |date=2015 |pmid=26479434 |doi=10.1016/j.ejogrb.2015.09.024 |hdl=11380/1073867 }}</ref> The use of the 40:1 ratio shows the same efficacy of ''myo''-inositol alone but in a shorter time. In addition, the physiological ratio does not impair oocyte quality.<ref>{{cite journal |last1=Colazingari |first1=S. |display-authors=etal |title=The combined therapy ''myo''-inositol plus D-''chiro''-inositol, rather than D-''chiro''-inositol, is able to improve IVF outcomes: results from a randomized controlled trial |journal=Archives of Gynecology and Obstetrics |volume=288 |issue=6 |pages=1405–11 |date=2013 |pmid=23708322 |doi=10.1007/s00404-013-2855-3 |s2cid=45611717}}</ref> | ||
The use of inositols in PCOS is gaining more importance, and an efficacy higher than 70% with a strong safety profile is reported. On the other hand, about 30% of patients could show as inositol-resistant.<ref>{{cite journal |last1=Kamenov |first1=Z. |display-authors=etal |title=Ovulation induction with ''myo''-inositol alone and in combination with clomiphene citrate in polycystic ovarian syndrome patients with insulin resistance |journal=Gynecological Endocrinology |volume=31 |issue=2 |pages=131–5 |date=2015 |pmid=25259724 |doi=10.3109/09513590.2014.964640 |s2cid=24469378}}</ref> New evidence regarding PCOS aetiopathogenesis describes an alteration in the species and the quantity of each strain characterizing the normal gastrointestinal flora. This alteration could lead to chronic, low-level inflammation and malabsorption.<ref>{{cite journal |last=González |first=F. |title=Inflammation in polycystic ovary syndrome: underpinning of insulin resistance and ovarian dysfunction |journal=Steroids |volume=77 |issue=4 |pages=300–5 |date=2012 |pmid=22178787 |doi=10.1016/j.steroids.2011.12.003 |pmc=3309040}}</ref> A possible solution could be represented by the combination of ''myo''-inositol and [[α-Lactalbumin|α-lactalbumin]]. This combination shows a synergic effect in increasing myo-inositol absorption.<ref>{{cite journal |last=Monastra |first=G. |display-authors=etal |title=''alpha''-Lactalbumin effect on ''myo''-inositol intestinal absorption: in vivo and in vitro. |journal=Current Drug Delivery |volume=15 |issue=9 |pages=1305–1311 |date=2018 |pmid=29745333 |doi=10.2174/1567201815666180509102641 |s2cid=13691602}}</ref> A recent study reported that the ''myo''-inositol and α-lactalbumin combination increases ''myo''-inositol plasmatic content in inositol-resistant patients with a relative improvement of hormonal and metabolic parameters.<ref>{{cite journal |last1=Oliva |first1=M. M. |display-authors=etal |title=Effects of ''myo''-inositol plus ''alpha''-lactalbumin in ''myo''-inositol-resistant PCOS women |journal=Journal of Ovarian Research |volume=11 |issue=1 |date=2018 | | The use of inositols in PCOS is gaining more importance, and an efficacy higher than 70% with a strong safety profile is reported. On the other hand, about 30% of patients could show as inositol-resistant.<ref>{{cite journal |last1=Kamenov |first1=Z. |display-authors=etal |title=Ovulation induction with ''myo''-inositol alone and in combination with clomiphene citrate in polycystic ovarian syndrome patients with insulin resistance |journal=Gynecological Endocrinology |volume=31 |issue=2 |pages=131–5 |date=2015 |pmid=25259724 |doi=10.3109/09513590.2014.964640 |hdl=11380/1075829 |s2cid=24469378}}</ref> New evidence regarding PCOS aetiopathogenesis describes an alteration in the species and the quantity of each strain characterizing the normal gastrointestinal flora. This alteration could lead to chronic, low-level inflammation and malabsorption.<ref>{{cite journal |last=González |first=F. |title=Inflammation in polycystic ovary syndrome: underpinning of insulin resistance and ovarian dysfunction |journal=Steroids |volume=77 |issue=4 |pages=300–5 |date=2012 |pmid=22178787 |doi=10.1016/j.steroids.2011.12.003 |pmc=3309040}}</ref> A possible solution could be represented by the combination of ''myo''-inositol and [[α-Lactalbumin|α-lactalbumin]]. This combination shows a synergic effect in increasing myo-inositol absorption.<ref>{{cite journal |last=Monastra |first=G. |display-authors=etal |title=''alpha''-Lactalbumin effect on ''myo''-inositol intestinal absorption: in vivo and in vitro. |journal=Current Drug Delivery |volume=15 |issue=9 |pages=1305–1311 |date=2018 |pmid=29745333 |doi=10.2174/1567201815666180509102641 |s2cid=13691602}}</ref> A recent study reported that the ''myo''-inositol and α-lactalbumin combination increases ''myo''-inositol plasmatic content in inositol-resistant patients with a relative improvement of hormonal and metabolic parameters.<ref>{{cite journal |last1=Oliva |first1=M. M. |display-authors=etal |title=Effects of ''myo''-inositol plus ''alpha''-lactalbumin in ''myo''-inositol-resistant PCOS women |journal=Journal of Ovarian Research |volume=11 |issue=1 |date=2018 |article-number=38 |pmid=29747700 |doi=10.1186/s13048-018-0411-2 |doi-access=free |pmc=5944130}}</ref> | ||
==Use as a cutting agent== | ==Use as a cutting agent== | ||
Inositol has been used as an adulterant or [[lacing (drugs)|cutting agent]] for many illegal drugs, such as [[cocaine]], [[methamphetamine]], and sometimes [[heroin]],<ref>{{cite web |title=Inositol, Nerve guidance, Cutting agent manufacturer |publisher=Tianyu Feed Additive |url=http://feedadditivechina.com/6-16-inositol.html |access-date=2013-07-21 | Inositol has been used as an adulterant or [[lacing (drugs)|cutting agent]] for many illegal drugs, such as [[cocaine]], [[methamphetamine]], and sometimes [[heroin]],<ref>{{cite web |title=Inositol, Nerve guidance, Cutting agent manufacturer |publisher=Tianyu Feed Additive |url=http://feedadditivechina.com/6-16-inositol.html |access-date=2013-07-21 |archive-url=https://web.archive.org/web/20140908220315/http://www.feedadditivechina.com/6-16-inositol.html |archive-date=2014-09-08}}</ref> probably because of its solubility, powdery texture, or reduced [[sweetness]] (50%) compared to more common sugars. | ||
Inositol is also used as a stand-in [[film prop]] for [[cocaine]] in [[filmmaking]].<ref>{{cite magazine |last=Golianopoulos |first=T. |title=Drug doubles: What actors actually toke, smoke and snort on camera |magazine=Wired |date=2012-05-12 |url=https://www.wired.com/underwire/2012/05/pl_drugs/ |access-date=2012-05-14 | Inositol is also used as a stand-in [[film prop]] for [[cocaine]] in [[filmmaking]].<ref>{{cite magazine |last=Golianopoulos |first=T. |title=Drug doubles: What actors actually toke, smoke and snort on camera |magazine=Wired |date=2012-05-12 |url=https://www.wired.com/underwire/2012/05/pl_drugs/ |access-date=2012-05-14 |archive-url=https://web.archive.org/web/20120514154908/http://www.wired.com/underwire/2012/05/pl_drugs/ |archive-date=2012-05-14}}</ref><ref>{{citation |title=How Fake Drugs Are Made For Movies {{!}} Movies Insider |date=12 December 2020 |language=en |url=https://www.youtube.com/watch?v=kwMuCwu-dqM |access-date=2022-09-26}}</ref> | ||
==Nutritional sources== | ==Nutritional sources== | ||
'' | ''Myo''-inositol is naturally present in a variety of foods, although tables of food composition do not always distinguish between [[lecithin]], the relatively bioavailable lipid form and the biounavailable phytate/phosphate form.<ref name='foods'>{{cite journal |last1=Clements |first1=R. S. |last2=Darnell |first2=B. |title=''myo''-Inositol content of common foods: development of a high-''myo''-inositol diet |journal=The American Journal of Clinical Nutrition |volume=33 |issue=9 |pages=1954–1967 |date=September 1980 |pmid=7416064 |doi=10.1093/ajcn/33.9.1954 |doi-access=free |s2cid=4442333}}</ref> Foods containing the highest concentrations of ''myo''-inositol and its compounds include fruits, beans, grains, and nuts.<ref name='foods'/> Fruits in particular, especially oranges and cantaloupe, contain the highest amounts of ''myo''-inositol.<ref name='sugar alcohol'>{{cite journal |last1=Awuchi |first1=Chinaza |title=Sugar Alcohols: Chemistry, Production, Health Concerns and Nutritional Importance of Mannitol, Sorbitol, Xylitol, and Erythritol |journal=International Journal of Advanced Academic Research |volume=5 |issue=11 |pages=1954–1967 |date=2017 |url=https://www.researchgate.net/publication/336923362}}</ref> It is also present in beans, nuts, and grains, however, these contain large amounts of ''myo''-inositol in the phytate form, which is not bioavailable without transformation by [[phytase]] enzymes. ''[[Bacillus subtilis]]'', the microorganism which produces the fermented food [[natto]], produces phytase enzymes that may convert [[phytic acid]] to a more bioavailable form of inositol polyphosphate in the gut.<ref>{{cite journal |vauthors=Borgi MA, Boudebbouze S, Mkaouar H, Maguin E, Rhimi M |title=Bacillus phytases: Current status and future prospects |journal=Bioengineered |volume=5 |issue=4 |pages=233–236 |date=2015 |pmid=25946551 |doi=10.1080/21655979.2015.1048050 |pmc=4601277}}</ref> Additionally, ''[[Bacteroides]]'' species in the gut secrete vesicles containing an active enzyme which converts the phytate molecule into bioavailable phosphorus and inositol polyphosphate, which is an important signaling molecule in the human body.<ref>{{cite journal |vauthors=Stentz R, Osborne S, Horn N, Li AW, Hautefort I, Bongaerts R, Rouyer M, Bailey P, Shears SB, Hemmings AM, Brearley CA, Carding SR |title=A Bacterial Homolog of a Eukaryotic Inositol Phosphate Signaling Enzyme Mediates Cross-kingdom Dialog in the Mammalian Gut |journal=Cell Reports |volume=6 |issue=4 |pages=646–656 |date=27 February 2014 |pmid=24529702 |doi=10.1016/j.celrep.2014.01.021 |doi-access=free |pmc=3969271}}</ref> | ||
'' | ''Myo''-inositol can also be found as an ingredient in [[energy drink]]s,<ref>{{cite journal |date=2019-08-01 |title=Risk assessment of energy drinks with focus on cardiovascular parameters and energy drink consumption in Europe |journal=Food and Chemical Toxicology |language=en |volume=130 |pages=109–121 |issn=0278-6915 |last1=Ehlers |first1=Anke |last2=Marakis |first2=Georgios |last3=Lampen |first3=Alfonso |last4=Hirsch-Ernst |first4=Karen Ildico |pmid=31112702 |doi=10.1016/j.fct.2019.05.028 |doi-access=free}}</ref> either in conjunction with or as a substitute for glucose.<ref>{{cite magazine |last=DiSalvo |first=David |title=We Know About Caffeine in Energy Drinks Like Monster, But What About the Other Ingredients? |magazine=Forbes |language=en |url=https://www.forbes.com/sites/daviddisalvo/2012/10/24/we-know-about-caffeine-in-energy-drinks-like-monster-but-what-about-the-other-ingredients/ |access-date=2020-12-22}}</ref> | ||
In humans, myo-inositol is naturally made from glucose-6-phosphate through enzymatic dephosphorylation.<ref name='sugar alcohol'/> | In humans, ''myo''-inositol is naturally made from glucose-6-phosphate through enzymatic dephosphorylation.<ref name='sugar alcohol'/> | ||
==Production== | ==Production== | ||
| Line 157: | Line 157: | ||
<ref name=liyu2021>Yunjie Li, Pingping Han, Juan Wang, Ting Shi, Chun You (2021): "Production of myo-inositol: Recent advance and prospective". ''Biotechnology and Applied Biochemistry'', volume 69, issue 3, pages 1101-1111. {{doi|10.1002/bab.2181}}</ref> | <ref name=liyu2021>Yunjie Li, Pingping Han, Juan Wang, Ting Shi, Chun You (2021): "Production of myo-inositol: Recent advance and prospective". ''Biotechnology and Applied Biochemistry'', volume 69, issue 3, pages 1101-1111. {{doi|10.1002/bab.2181}}</ref> | ||
<ref name=maju2006>{{cite book |title=Biology of Inositols and Phosphoinositides |last1=Majumder |first1=A. L. |last2=Biswas |first2=B. B. |date=2006-10-03 |publisher=Springer Science & Business Media |isbn= | <ref name=maju2006>{{cite book |title=Biology of Inositols and Phosphoinositides |last1=Majumder |first1=A. L. |last2=Biswas |first2=B. B. |date=2006-10-03 |publisher=Springer Science & Business Media |isbn=978-0-387-27600-7 |language=en |url=https://books.google.com/books?id=vxoxBbmiLQUC&pg=PA3}}</ref> | ||
<ref name=reyn1993>J. E. F. Reynolds (1993): '' Martindale: The Extra Pharmacopoeia'', volume 30. Quote (page 1379): "An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man". {{ISBN|978-0-85369-300-0}}</ref> | <ref name=reyn1993>J. E. F. Reynolds (1993): '' Martindale: The Extra Pharmacopoeia'', volume 30. Quote (page 1379): "An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man". {{ISBN|978-0-85369-300-0}}</ref> | ||
Latest revision as of 08:40, 6 November 2025
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| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | 180.16 g/mol |
| Density | 1.752 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
| Template:Longitem | −1329.3 kJ/mol |
| Template:Longitem | −2747 kJ/mol |
| Template:Longitem | A11HA07 (WHO) |
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In biochemistry, medicine, and related sciences, inositol generally refers to myo-inositol (formerly meso-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its formula is Template:Chem2; the molecule has a ring of six carbon atoms, each with a hydrogen atom and a hydroxy group (–OH). In myo-inositol, two of the hydroxyls, neither adjacent nor opposite, lie above the respective hydrogens relative to the mean plane of the ring.
The compound is a carbohydrate, specifically a sugar alcohol (as distinct from simple sugars like glucose) with half the sweetness of sucrose (table sugar). It is one of the most ancient components of living beings with multiple functions in eukaryotes, including structural lipids and secondary messengers.[2] A human kidney makes about two grams per day from glucose, but other tissues synthesize it too. The highest concentration is in the brain, where it plays an important role in making other neurotransmitters and some steroid hormones bind to their receptors.[3] In other tissues, it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation.[4] In most mammalian cells the concentrations of myo-inositol are 5 to 500 times greater inside cells than outside them.[5]
A 2023 meta-analysis found that inositol is a safe and effective treatment in the management of polycystic ovary syndrome (PCOS).[6] However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS.[7]
The other naturally occurring stereoisomers of cyclohexane-1,2,3,4,5,6-hexol are scyllo-, muco-, DScript error: No such module "Check for unknown parameters".-chiro-, LScript error: No such module "Check for unknown parameters".-chiro-, and neo-inositol, although they occur in minimal quantities compared to myo-inositol. The other possible isomers are allo-, epi-, and cis-inositol.
History
myo-Inositol was first isolated from muscle extracts by Johanes Joseph Scherer (1814–1869) in 1850.[2] It was formerly called meso-inositol to distinguish it from the chiro- isomers. However, since all other isomers are meso (non-chiral) compounds, the name myo-inositol is now preferred (myo- being a medical prefix for "muscle").
Inositol was once considered a member of the vitamin B complex, namely vitamin B8 before the discovery that it is made naturally in the human body, and therefore cannot be a vitamin or essential nutrient.[8]
Chemical properties
myo-Inositol is a meso compound, meaning it is optically inactive because it has a plane of symmetry.[9] It is a white crystalline powder, relatively stable in the air. It is highly soluble in water, slightly soluble in glacial acetic acid, ethanol, glycol, and glycerin, but insoluble in chloroform and ether.[2]
In its most stable conformation, the myo-inositol isomer assumes the chair conformation, which moves the maximum number of hydroxyls to the equatorial position, where they are farthest apart from each other. In this conformation, the natural myo isomer has a structure in which five of the six hydroxyls (the first, third, fourth, fifth, and sixth) are equatorial, whereas the second hydroxyl group is axial.[10]
Physiological roles
Myo-Inositol plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells, the various inositol phosphates. In addition, inositol serves as an important component of the structural lipids phosphatidylinositol (PI) and its various phosphates, the phosphatidylinositol phosphate (PIP) lipids.
Biosynthesis
In humans, myo-Inositol is synthesized de novo but DScript error: No such module "Check for unknown parameters".-chiro-inositol is not.[5] myo-Inositol is synthesized from glucose 6-phosphate (G6P) in two steps. First, G6P is isomerised by an inositol-3-phosphate synthase enzyme (for example, ISYNA1) to myo-inositol 1-phosphate, which is then dephosphorylated by an inositol monophosphatase enzyme (for example, IMPA1) to give free myo-inositol. In humans, most inositol is synthesized in the kidneys, followed by testicles, typically in amounts of a few grams per day.[4]
At the peripheral level, myo-inositol is converted to DScript error: No such module "Check for unknown parameters".-chiro-inositol by a specific epimerase. Only a minor fraction of myo-inositol is converted into DScript error: No such module "Check for unknown parameters".-chiro-inositol.[5] The activity of this epimerase is insulin dependent, causing a reduction of DScript error: No such module "Check for unknown parameters".-chiro-inositol in muscle, fat, and liver when there is insulin resistance.[11][5] DScript error: No such module "Check for unknown parameters".-chiro-inositol reduces the conversion of testosterone to estrogen, thereby increases the levels of testosterone and worsening PCOS.[5]
Phytic acid in plants
Inositol hexaphosphate, also called phytic acid or IP6, is a phytochemical and the principal storage form of phosphorus in many plant tissues, especially bran and seed.[12] Phosphorus and inositol in phytate form are not generally bioavailable to non-ruminant animals because these animals lack the digestive enzyme phytase required to remove the phosphate groups. Ruminants readily digest phytate because of the phytase produced by microorganisms in the rumen.[13] Moreover, phytic acid also chelates important minerals such as calcium, magnesium, iron, and zinc, making them unabsorbable, and contributing to mineral deficiencies in people whose diets rely highly on bran and seeds for their mineral intake, such as occurs in developing countries.[14][15] Because of this, phytic acid is considered as an antinutrient.
Inositol penta- (IP5), tetra- (IP4), and triphosphate (IP3) are also called "phytates".
Inositol or its phosphates and associated lipids are found in many foods, in particular fruit, especially cantaloupe and oranges.[16] In plants, the hexaphosphate of inositol, phytic acid or its salts, the phytates, serve as phosphate stores in seed, for example in nuts and beans.[17] Phytic acid also occurs in cereals with high bran content. Phytate is, however, not directly bioavailable to humans in the diet, since it is not digestible. Some food preparation techniques partly break down phytates to change this. However, inositol in the form of phospholipids, as found in certain plant-derived substances such as lecithins, is well absorbed and relatively bioavailable.
Biological function
Inositol, phosphatidylinositol, and some of their mono- and polyphosphates function as secondary messengers in a number of intracellular signal transduction pathways. They are involved in a number of biological processes, including:
- Insulin signal transduction[18]
- Cytoskeleton assembly
- Nerve guidance (epsin)
- Intracellular calcium (Ca2+) concentration control[19]
- Cell membrane potential maintenance[20]
- Breakdown of fats[21]
- Gene expression[22][23]
In one important family of pathways, phosphatidylinositol 4,5-bisphosphate (PIP2) is stored in cellular membranes until it is released by any of a number of signalling proteins and transformed into various secondary messengers, for example diacylglycerol and inositol trisphosphate.[24]
'myo-Inositol has very low toxicity, with a reported LD50 10,000 mg/kg body weight (oral) in rats.[2]
Industrial uses
Explosives industry
At the 1936 meeting of the American Chemical Society, professor Edward Bartow of the University of Iowa presented a commercially viable means of extracting large amounts of inositol from the phytic acid naturally present in waste corn. As a possible use for the chemical, he suggested 'inositol nitrate' as a more stable alternative to nitroglycerin.[25] Today, inositol nitrate is used to gelatinize nitrocellulose in many modern explosives and solid rocket propellants.[26]
Road salt
When plants are exposed to increasing concentrations of road salt, the plant cells become dysfunctional and undergo apoptosis, leading to inhibited growth. Inositol pretreatment could reduce these effects.[27]
Research and clinical applications
Trichotillomania
High doses of inositol have been explored for treatment of trichotillomania (compulsive hair-pulling) and related disorders, but no definitive evidence points to its effectiveness.[28]
Other illnesses
D-chiro-inositol is an important messenger molecule in insulin signaling.[29] Inositol supplementation has been shown to significantly decrease triglycerides and LDL cholesterol in patients with metabolic diseases.[29]
myo-Inositol is important for thyroid hormone synthesis.[30] Depletion of myo-inositol may predispose to development of hypothyroidism.[30] Patients with hypothyroidism have a higher demand for myo-inositol than healthy subjects.[30]
Inositol should not be routinely implemented for the management of preterm babies who have or are at a risk of infant respiratory distress syndrome (RDS).[31] Myo-inositol helps prevent neural tube defects with particular efficacy in combination with folic acid.[32]
Inositol is considered a safe and effective treatment for polycystic ovary syndrome (PCOS).[6] It works by increasing insulin sensitivity, which helps to improve ovarian function and reduce hyperandrogenism.[33] It is also shown to reduce the risk of metabolic disease in women with PCOS.[34] In addition, thanks to its role as FSH second messenger, myo-inositol is effective in restoring FSH/LH ratio and menstrual cycle regularization.[35] myo-Inositol's role as FSH second messenger leads to a correct ovarian follicle maturation and consequently to a higher oocyte quality. Improving the oocyte quality in both women with or without PCOS, myo-inositol can be considered as a possible approach for increasing the chance of success in assisted reproductive technologies.[36][37] In contrast, DScript error: No such module "Check for unknown parameters".-chiro-inositol can impair oocyte quality in a dose-dependent manner.[38] The high level of DCI seems to be related to elevated insulin levels retrieved in about 70% of PCOS women.[39] In this regard, insulin stimulates the irreversible conversion of myo-inositol to DScript error: No such module "Check for unknown parameters".-chiro-inositol causing a drastic reduction of myo-inositol. myo-Inositol depletion is particularly damaging to ovarian follicles because it is involved in FSH signaling, which is impaired due to myo-inositol depletion.[11] Recent evidence reports a faster improvement of the metabolic and hormonal parameters when these two isomers are administered in their physiological ratio. The plasmatic ratio of myo-inositol and DScript error: No such module "Check for unknown parameters".-chiro-inositol in healthy subjects is 40:1 of myo- and DScript error: No such module "Check for unknown parameters".-chiro-inositol respectively.[40] The use of the 40:1 ratio shows the same efficacy of myo-inositol alone but in a shorter time. In addition, the physiological ratio does not impair oocyte quality.[41]
The use of inositols in PCOS is gaining more importance, and an efficacy higher than 70% with a strong safety profile is reported. On the other hand, about 30% of patients could show as inositol-resistant.[42] New evidence regarding PCOS aetiopathogenesis describes an alteration in the species and the quantity of each strain characterizing the normal gastrointestinal flora. This alteration could lead to chronic, low-level inflammation and malabsorption.[43] A possible solution could be represented by the combination of myo-inositol and α-lactalbumin. This combination shows a synergic effect in increasing myo-inositol absorption.[44] A recent study reported that the myo-inositol and α-lactalbumin combination increases myo-inositol plasmatic content in inositol-resistant patients with a relative improvement of hormonal and metabolic parameters.[45]
Use as a cutting agent
Inositol has been used as an adulterant or cutting agent for many illegal drugs, such as cocaine, methamphetamine, and sometimes heroin,[46] probably because of its solubility, powdery texture, or reduced sweetness (50%) compared to more common sugars.
Inositol is also used as a stand-in film prop for cocaine in filmmaking.[47][48]
Nutritional sources
Myo-inositol is naturally present in a variety of foods, although tables of food composition do not always distinguish between lecithin, the relatively bioavailable lipid form and the biounavailable phytate/phosphate form.[16] Foods containing the highest concentrations of myo-inositol and its compounds include fruits, beans, grains, and nuts.[16] Fruits in particular, especially oranges and cantaloupe, contain the highest amounts of myo-inositol.[49] It is also present in beans, nuts, and grains, however, these contain large amounts of myo-inositol in the phytate form, which is not bioavailable without transformation by phytase enzymes. Bacillus subtilis, the microorganism which produces the fermented food natto, produces phytase enzymes that may convert phytic acid to a more bioavailable form of inositol polyphosphate in the gut.[50] Additionally, Bacteroides species in the gut secrete vesicles containing an active enzyme which converts the phytate molecule into bioavailable phosphorus and inositol polyphosphate, which is an important signaling molecule in the human body.[51]
Myo-inositol can also be found as an ingredient in energy drinks,[52] either in conjunction with or as a substitute for glucose.[53]
In humans, myo-inositol is naturally made from glucose-6-phosphate through enzymatic dephosphorylation.[49]
Production
As of 2021, the main industrial process for the production of myo-inositol (mostly in China and Japan) started with phytate (IP6) extracted from the soaking water resulting from corn and rice bran processing. After purification, the phytate is hydrolized, and myo-inositol is separated by crystallization.[2]
Another route is microbial fermentation of carbohydrates by various organisms, such as the fungus Neurospora crassa (Beadle and Tatum, 1945), Candida boidini (Shirai et al., 1997), Saccharomyces cerevisiae (Culbertson et al., 1976), Escherichia coli (Hansen, 1999).[2] Alternatively, enzyme extracts from microbial cultures can be used in vitro to obtain myo-inositol from various substrates, including glucose, sucrose, starch, xylose, and amylose.[2]
References
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- ↑ a b c d e f g h Yunjie Li, Pingping Han, Juan Wang, Ting Shi, Chun You (2021): "Production of myo-inositol: Recent advance and prospective". Biotechnology and Applied Biochemistry, volume 69, issue 3, pages 1101-1111. Script error: No such module "CS1 identifiers".
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External links
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