Tartaric acid: Difference between revisions
Jump to navigation
Jump to search
imported>Artoria2e5 →Toxicity in canines: No, just the domestic dog. In the "canid" interpretation of canine we include foxes and jackals which handle them just fine. |
|||
| Line 10: | Line 10: | ||
| ImageSize = | | ImageSize = | ||
| PIN = 2,3-Dihydroxybutanedioic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> | | PIN = 2,3-Dihydroxybutanedioic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> | ||
| SystematicName = (2''R'', 3''R'')-Threaric acid (+)<br>(2''S'', 3''S'')-Threaric acid (-)<ref>In the older literature, there is confusion about the use of D and L in the case of tartaric acids. It is therefore recommended to use the R,S system in this case.</ref><br>''meso''-Erythraric acid<ref>{{cite web | url=https://iupac.qmul.ac.uk/2carb/23.html | title=2-Carb-23 }}</ref> | | SystematicName = (2''R'', 3''R'')-Threaric acid (+)<br />(2''S'', 3''S'')-Threaric acid (-)<ref>In the older literature, there is confusion about the use of D and L in the case of tartaric acids. It is therefore recommended to use the R,S system in this case.</ref><br />''meso''-Erythraric acid<ref>{{cite web | url=https://iupac.qmul.ac.uk/2carb/23.html | title=2-Carb-23 }}</ref> | ||
| OtherNames = Tartaric acid<br />2,3-Dihydroxysuccinic acid<br />Threaric acid<br />Racemic acid<br />Uvic acid<br />Paratartaric acid<br />Winestone | | OtherNames = Tartaric acid<br />2,3-Dihydroxysuccinic acid<br />Threaric acid<br />Racemic acid<br />Uvic acid<br />Paratartaric acid<br />Winestone | ||
| IUPACName = Tartaric acid<ref>{{cite web | url=https://iupac.qmul.ac.uk/2carb/23.html | title=2-Carb-23 }}</ref> | | IUPACName = Tartaric acid<ref>{{cite web | url=https://iupac.qmul.ac.uk/2carb/23.html | title=2-Carb-23 }}</ref> | ||
| Reference = <ref name="pubchem">[https://pubchem.ncbi.nlm.nih.gov/ | | Reference = <ref name="pubchem">[https://pubchem.ncbi.nlm.nih.gov/compound/875 Tartaric Acid – Compound Summary], [[PubChem]].</ref> | ||
| Section1 = {{Chembox Identifiers | | Section1 = {{Chembox Identifiers | ||
| index_label = | | index_label = | ||
| Line 61: | Line 61: | ||
}} | }} | ||
| Section2 = {{Chembox Properties | | Section2 = {{Chembox Properties | ||
| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>6</sub> (basic formula)<br>HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H (structural formula) | | Formula = C<sub>4</sub>H<sub>6</sub>O<sub>6</sub> (basic formula)<br />HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H (structural formula) | ||
| MolarMass = 150.087{{nbsp}}g/mol | | MolarMass = 150.087{{nbsp}}g/mol | ||
| Appearance = White powder | | Appearance = White powder | ||
| Line 72: | Line 72: | ||
| 1.25{{nbsp}}kg/L ("meso") | | 1.25{{nbsp}}kg/L ("meso") | ||
}} | }} | ||
| pKa = L(+) 25{{nbsp}}°C :<br>pK<sub>a1</sub>= 2.89, pK<sub>a2</sub>= 4.40<br>meso 25{{nbsp}}°C:<br>pK<sub>a1</sub>= 3.22, pK<sub>a2</sub>= 4.85 | | pKa = L(+) 25{{nbsp}}°C :<br />pK<sub>a1</sub>= 2.89, pK<sub>a2</sub>= 4.40<br />meso 25{{nbsp}}°C:<br />pK<sub>a1</sub>= 3.22, pK<sub>a2</sub>= 4.85 | ||
<ref>Dawson, R.M.C. et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref> | <ref>Dawson, R.M.C. et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref> | ||
| ConjugateBase = [[Bitartrate]] | | ConjugateBase = [[Bitartrate]] | ||
| Line 91: | Line 91: | ||
}} | }} | ||
}} | }} | ||
{{Distinguish|tartronic acid}} | |||
'''Tartaric acid''' is a white, crystalline [[organic acid]] that occurs naturally in many fruits, most notably in [[grape]]s but also in [[tamarind]]s, [[banana]]s, [[avocado]]s, and [[citrus]].<ref name="pubchem"/> Its [[salt (chemistry)|salt]], [[potassium bitartrate]], commonly known as cream of tartar, develops naturally in the process of [[winemaking|fermentation]]. Potassium bitartrate is commonly mixed with [[sodium bicarbonate]] and is sold as [[baking powder]] used as a [[leavening agent]] in food preparation. The acid itself is added to foods as an [[antioxidant]] [[E-numbers|E334]] and to impart its distinctive sour taste. [[Naturally occurring]] tartaric acid is a useful raw material in [[organic synthesis]]. Tartaric acid, an alpha-hydroxy-[[carboxylic acid]], is [[diprotic acid|diprotic]] and [[aldaric acid|aldaric]] in acid characteristics and is a dihydroxyl derivative of [[succinic acid]]. | '''Tartaric acid''' is a white, crystalline [[organic acid]] that occurs naturally in many fruits, most notably in [[grape]]s but also in [[tamarind]]s, [[banana]]s, [[avocado]]s, and [[citrus]].<ref name="pubchem"/> Its [[salt (chemistry)|salt]], [[potassium bitartrate]], commonly known as cream of tartar, develops naturally in the process of [[winemaking|fermentation]]. Potassium bitartrate is commonly mixed with [[sodium bicarbonate]] and is sold as [[baking powder]] used as a [[leavening agent]] in food preparation. The acid itself is added to foods as an [[antioxidant]] [[E-numbers|E334]] and to impart its distinctive sour taste. [[Naturally occurring]] tartaric acid is a useful raw material in [[organic synthesis]]. Tartaric acid, an alpha-hydroxy-[[carboxylic acid]], is [[diprotic acid|diprotic]] and [[aldaric acid|aldaric]] in acid characteristics and is a dihydroxyl derivative of [[succinic acid]]. | ||
==History== | ==History== | ||
Tartaric acid has been known to [[winemakers]] for | Tartaric acid has been known to [[winemakers]] for centuries– its crude crystalline form as found off top of wine barrels were called {{wikt-lang|la|tartarum}} (rendered ''tartre'' by [[Geoffrey Chaucer|Chaucer]]) or "wine stone".<ref>{{cite book |last=Rösslin |first=Eucharius (the Younger)|editor-last1=Belkin |editor-first1=Johanna Schwind |editor-last2=Caley |editor-first2=Earle Radcliffe |title=On minerals and mineral products: chapters on minerals from his « Kreutterbuch » |date=1978 |publisher=W. de Gruyter |location=Berlin |isbn=3-11-006907-5 |pages=315-6}}</ref> However, chemical extraction and purification was developed in 1769 by the [[Sweden|Swedish]] chemist [[Carl Wilhelm Scheele]].<ref>Retzius, Anders Jahan (1770) [https://babel.hathitrust.org/cgi/pt?id=mdp.39015039452886;view=1up;seq=605 "Försök med vinsten och dess syra"] (Experiments with cream of tartar and its acid), ''Kungliga Vetenskapsakademiens Handlingar'' (Proceedings of the Royal Academy of Sciences), '''31''' : 207–213. [https://babel.hathitrust.org/cgi/pt?id=mdp.39015039452886;view=1up;seq=607 From p. 209:] ''"§. 6. Dessa försök omtalte jag för Hr. Carl Wilhelm Scheele (en snabb och lårgirug Pharmaciæ Studiosus) … "'' (§. 6. I mention these experiments on behalf of Mr. Carl Wilhelm Scheele (a quick and studious student of pharmacology) … )</ref> | ||
Tartaric acid played an important role in the discovery of [[chirality (chemistry)|chemical chirality]]. This property of tartaric acid was first observed in 1832 by [[Jean Baptiste Biot]], who observed its ability to rotate [[Polarization (waves)|polarized light]].<ref>Biot (1835) [http://gallica.bnf.fr/ark:/12148/bpt6k32283/f149.image "Mémoire sur la polarization circulaire et sur ses applications à la chimie organique"] (Memoir on circular polarization and on its applications to organic chemistry), ''Mémoires de l'Académie des sciences de l'Institut'', 2nd series, '''13''' : 39–175. That tartaric acid (''acide tartarique cristallisé'') rotates plane-polarized light is shown in [http://gallica.bnf.fr/ark:/12148/bpt6k32283/f285.image Table G following p. 168.] (Note: This article was read to the French Royal Academy of Sciences on 1832 November 5.)</ref><ref>Biot (1838) [https://babel.hathitrust.org/cgi/pt?id=mdp.39015077785536;view=1up;seq=145 "Pour discerner les mélanges et les combinaisons chimiques définies ou non définies, qui agissent sur la lumière polarisée; suivies d'applications aux combinaisons de l'acide tartarique avec l'eau, l'alcool et l'esprit de bois"] (In order to discern mixtures and chemical combinations, defined or undefined, which act on polarized light; followed by applications to combinations of tartaric acid with water, alcohol [i.e., ethanol], and spirit of wood [i.e., methanol]), ''Mémoires de l'Académie des sciences de l'Institut'', 2nd series, '''15''' : 93–279.</ref> [[Louis Pasteur]] continued this research in 1847 by investigating the shapes of [[sodium ammonium tartrate]] crystals, which he found to be chiral. By manually sorting the differently shaped crystals, Pasteur was the first to produce a pure sample of levotartaric acid.<ref>{{cite journal |last1=Pasteur |first1=L. |title=Mémoire sur la relation qui peut exister entre la forme cristalline et la composition chimique, et sur la cause de la polarisation rotatoire |journal=Comptes rendus de l'Académie des Sciences de Paris |date=1848 |volume=26 |pages=535–538 |url=https://www.biodiversitylibrary.org/item/21163#page/545/mode/1up |trans-title=Memoir on the relationship which can exist between crystalline form and chemical composition, and on the cause of rotary polarization |language=French}}</ref><ref>L. Pasteur (1848) [https://books.google.com/books?id=gJ45AAAAcAAJ&pg=PA442 "Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire"] (On the relations that can exist between crystalline form, and chemical composition, and the sense of rotary polarization), ''Annales de Chimie et de Physique'', 3rd series, '''24''' : 442–459.</ref><ref>Pasteur, Louis (1850) [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy7;view=1up;seq=66 "Recherches sur les propriétés spécifiques des deux acides qui composent l'acide racémique"] [Investigations into the specific properties of the two acids that compose racemic acid], ''Annales de Chimie et de Physique'', 3rd series, '''28''' (3) : 56–99. See also [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy7;view=1up;seq=519 Plate II.] (See also the report of the commission that was appointed to verify Pasteur's findings, pp. 99–117.) [in French]</ref><ref>{{cite journal |author1=George B. Kauffman |author2=Robin D. Myers |year=1998 |url=http://192.129.24.144/licensed_materials/00897/papers/0003006/36kau897.pdf |title=Pasteur's resolution of racemic acid: A sesquicentennial retrospect and a new translation |journal=The Chemical Educator |volume=3 |issue=6 |pages=1–4 |doi=10.1007/s00897980257a |s2cid=95862598 | Tartaric acid played an important role in the discovery of [[chirality (chemistry)|chemical chirality]]. This property of tartaric acid was first observed in 1832 by [[Jean Baptiste Biot]], who observed its ability to rotate [[Polarization (waves)|polarized light]].<ref>Biot (1835) [http://gallica.bnf.fr/ark:/12148/bpt6k32283/f149.image "Mémoire sur la polarization circulaire et sur ses applications à la chimie organique"] (Memoir on circular polarization and on its applications to organic chemistry), ''Mémoires de l'Académie des sciences de l'Institut'', 2nd series, '''13''' : 39–175. That tartaric acid (''acide tartarique cristallisé'') rotates plane-polarized light is shown in [http://gallica.bnf.fr/ark:/12148/bpt6k32283/f285.image Table G following p. 168.] (Note: This article was read to the French Royal Academy of Sciences on 1832 November 5.)</ref><ref>Biot (1838) [https://babel.hathitrust.org/cgi/pt?id=mdp.39015077785536;view=1up;seq=145 "Pour discerner les mélanges et les combinaisons chimiques définies ou non définies, qui agissent sur la lumière polarisée; suivies d'applications aux combinaisons de l'acide tartarique avec l'eau, l'alcool et l'esprit de bois"] (In order to discern mixtures and chemical combinations, defined or undefined, which act on polarized light; followed by applications to combinations of tartaric acid with water, alcohol [i.e., ethanol], and spirit of wood [i.e., methanol]), ''Mémoires de l'Académie des sciences de l'Institut'', 2nd series, '''15''' : 93–279.</ref> [[Louis Pasteur]] continued this research in 1847 by investigating the shapes of [[sodium ammonium tartrate]] crystals, which he found to be chiral. By manually sorting the differently shaped crystals, Pasteur was the first to produce a pure sample of levotartaric acid.<ref>{{cite journal |last1=Pasteur |first1=L. |title=Mémoire sur la relation qui peut exister entre la forme cristalline et la composition chimique, et sur la cause de la polarisation rotatoire |journal=Comptes rendus de l'Académie des Sciences de Paris |date=1848 |volume=26 |pages=535–538 |url=https://www.biodiversitylibrary.org/item/21163#page/545/mode/1up |trans-title=Memoir on the relationship which can exist between crystalline form and chemical composition, and on the cause of rotary polarization |language=French}}</ref><ref>L. Pasteur (1848) [https://books.google.com/books?id=gJ45AAAAcAAJ&pg=PA442 "Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire"] (On the relations that can exist between crystalline form, and chemical composition, and the sense of rotary polarization), ''Annales de Chimie et de Physique'', 3rd series, '''24''' : 442–459.</ref><ref>Pasteur, Louis (1850) [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy7;view=1up;seq=66 "Recherches sur les propriétés spécifiques des deux acides qui composent l'acide racémique"] [Investigations into the specific properties of the two acids that compose racemic acid], ''Annales de Chimie et de Physique'', 3rd series, '''28''' (3) : 56–99. See also [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy7;view=1up;seq=519 Plate II.] (See also the report of the commission that was appointed to verify Pasteur's findings, pp. 99–117.) [in French]</ref><ref>{{cite journal |author1=George B. Kauffman |author2=Robin D. Myers |year=1998 |url=http://192.129.24.144/licensed_materials/00897/papers/0003006/36kau897.pdf |title=Pasteur's resolution of racemic acid: A sesquicentennial retrospect and a new translation |journal=The Chemical Educator |volume=3 |issue=6 |pages=1–4 |doi=10.1007/s00897980257a |s2cid=95862598 |archive-url=https://web.archive.org/web/20060117144722/http://192.129.24.144/licensed_materials/00897/papers/0003006/36kau897.pdf |archive-date=2006-01-17}}</ref><ref name=Flack>{{cite journal |author=Flack, H.D. |year=2009 |url=http://crystal.flack.ch/sh5092.pdf |title=Louis Pasteur's discovery of molecular chirality and spontaneous resolution in 1848, together with a complete review of his crystallographic and chemical work |journal=Acta Crystallographica A |volume=65 |issue=5 |pages=371–389 |pmid=19687573 |doi=10.1107/S0108767309024088 |bibcode=2009AcCrA..65..371F |archive-url=https://wayback.archive-it.org/all/20120906001007/http://crystal.flack.ch/sh5092.pdf |archive-date=2012-09-06}}</ref> | ||
== Stereochemistry == | == Stereochemistry == | ||
| Line 104: | Line 105: | ||
Naturally occurring form of the acid is '''dextro tartaric acid ''' or '''<small>L</small>-(+)-tartaric acid''' (obsolete name [[Descriptor (Chemistry)#dl|''d'']]-tartaric acid). Because it is available naturally, it is cheaper than its [[enantiomer]] and the [[meso isomer]]. The ''dextro'' and ''levo'' prefixes are archaic terms.<ref>{{Cite web |url=https://cosmolearning.org/video-lectures/stereochemical-nomenclature-racemization-and-resolution-6674/ |title=Lecture 28: Stereochemical Nomenclature; Racemization and Resolution | CosmoLearning Chemistry |website=CosmoLearning}}</ref> Modern textbooks refer to the natural form as (2''R'',3''R'')-tartaric acid '''('''<small>L</small>'''-(+)-tartaric acid)''', and its enantiomer as (2''S'',3''S'')-tartaric acid '''('''D'''-(−)-tartaric acid)'''. The ''meso'' diastereomer is referred to as (2''R'',3''S'')-tartaric acid or (2''S'',3''R'')-tartaric acid. | Naturally occurring form of the acid is '''dextro tartaric acid ''' or '''<small>L</small>-(+)-tartaric acid''' (obsolete name [[Descriptor (Chemistry)#dl|''d'']]-tartaric acid). Because it is available naturally, it is cheaper than its [[enantiomer]] and the [[meso isomer]]. The ''dextro'' and ''levo'' prefixes are archaic terms.<ref>{{Cite web |url=https://cosmolearning.org/video-lectures/stereochemical-nomenclature-racemization-and-resolution-6674/ |title=Lecture 28: Stereochemical Nomenclature; Racemization and Resolution | CosmoLearning Chemistry |website=CosmoLearning}}</ref> Modern textbooks refer to the natural form as (2''R'',3''R'')-tartaric acid '''('''<small>L</small>'''-(+)-tartaric acid)''', and its enantiomer as (2''S'',3''S'')-tartaric acid '''('''D'''-(−)-tartaric acid)'''. The ''meso'' diastereomer is referred to as (2''R'',3''S'')-tartaric acid or (2''S'',3''R'')-tartaric acid. | ||
* Dextro and levo form [[Crystal structure|monoclinic sphenoidal]] crystals<ref>{{cite journal |last1=W, T, Astbury |title=The Crystalline Structure and Properties of Tartaric Acid |journal=Proc. R. Soc. A |date=Feb 1923 |volume=102|issue=718 |pages=506–528 | doi=10.1098/rspa.1923.0010 |bibcode=1923RSPSA.102..506A |doi-access=free }}, based on P. | * Dextro and levo form [[Crystal structure|monoclinic sphenoidal]] crystals<ref>{{cite journal |last1=W, T, Astbury |title=The Crystalline Structure and Properties of Tartaric Acid |journal=Proc. R. Soc. A |date=Feb 1923 |volume=102|issue=718 |pages=506–528 | doi=10.1098/rspa.1923.0010 |bibcode=1923RSPSA.102..506A |doi-access=free }}, based on P. Groth's "Chemische Krystallographie".</ref> and [[orthorhombic]] crystals. | ||
* Racemic tartaric acid forms [[monoclinic]]<ref name=CRC49>CRC Handbook of Chemistry and Physics, 49th edition.</ref> and [[triclinic]] crystals ([[space group]] P{{overline|1}}).<ref>{{cite web|date=2008 |last1=Samantha Callear and Michael Hursthouse |title=D-Tartaric acid |url=http://www.crystallography.net/cod/1519959.html |website=Crystallography Open Database}}</ref><ref>{{cite journal |display-authors=etal|last1=Paul Luner |title=(+-)-Tartaric acid |journal=Acta Crystallographica Section C |date=Jul 2002 |volume=58 |issue=6 |pages=o333–o335 |doi=10.1107/S0108270102006650 |pmid=12050433 |bibcode=2002AcCrC..58O.333L |url=https://www.researchgate.net/publication/11324000}}, {{cite web |title=(±)-Tartaric acid |url=http://www.crystallography.net/cod/2012731.html |website=Crystallography Open Database|year=2002 }}</ref> | * Racemic tartaric acid forms [[monoclinic]]<ref name=CRC49>CRC Handbook of Chemistry and Physics, 49th edition.</ref> and [[triclinic]] crystals ([[space group]] P{{overline|1}}).<ref>{{cite web|date=2008 |last1=Samantha Callear and Michael Hursthouse |title=D-Tartaric acid |url=http://www.crystallography.net/cod/1519959.html |website=Crystallography Open Database}}</ref><ref>{{cite journal |display-authors=etal|last1=Paul Luner |title=(+-)-Tartaric acid |journal=Acta Crystallographica Section C |date=Jul 2002 |volume=58 |issue=6 |pages=o333–o335 |doi=10.1107/S0108270102006650 |pmid=12050433 |bibcode=2002AcCrC..58O.333L |url=https://www.researchgate.net/publication/11324000}}, {{cite web |title=(±)-Tartaric acid |url=http://www.crystallography.net/cod/2012731.html |website=Crystallography Open Database|year=2002 }}</ref> | ||
* Anhydrous meso tartaric acid form two anhydrous [[polymorphism (materials science)|polymorphs]]: triclinic and orthorhombic. | * Anhydrous meso tartaric acid form two anhydrous [[polymorphism (materials science)|polymorphs]]: triclinic and orthorhombic. | ||
| Line 117: | Line 118: | ||
! levotartaric acid<br/><small>(D-(−)-tartaric acid)</small> | ! levotartaric acid<br/><small>(D-(−)-tartaric acid)</small> | ||
|- | |- | ||
| width="150" | [[File:L-tartaric acid. | | width="150" | [[File:L-tartaric acid.svg|150px|class=skin-invert-image]] | ||
| width="150" | [[File:D-tartaric acid. | | width="150" | [[File:D-tartaric acid.svg|150px|class=skin-invert-image]] | ||
| width="270" | [[File:Meso-Weinsäure Spiegel.svg|150 px|class=skin-invert-image]] | | width="270" | [[File:Meso-Weinsäure Spiegel.svg|150 px|class=skin-invert-image]] | ||
|} | |} | ||
{| class="wikitable" | {| class="wikitable" | ||
|+ Forms of tartaric acid | |+ Forms of tartaric acid | ||
| Line 136: | Line 136: | ||
| | | | ||
| style="vertical-align:top" | (2''S'',3''S'')-tartaric acid <br/> (''S'',''S'')-tartaric acid <br/> (−)-tartaric acid <br/> ''l''-tartaric acid <small>''(obsolete)''</small> <br/> levotartaric acid <br/> {{sc|D}}-tartaric acid <br/> {{sc|D}}-threaric acid <br/>("unnatural isomer")<ref>{{Cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/439655 |title=d-Tartaric acid |website=[[PubChem]]}}</ref> | | style="vertical-align:top" | (2''S'',3''S'')-tartaric acid <br/> (''S'',''S'')-tartaric acid <br/> (−)-tartaric acid <br/> ''l''-tartaric acid <small>''(obsolete)''</small> <br/> levotartaric acid <br/> {{sc|D}}-tartaric acid <br/> {{sc|D}}-threaric acid <br/>("unnatural isomer")<ref>{{Cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/439655 |title=d-Tartaric acid |website=[[PubChem]]}}</ref> | ||
| style="vertical-align:top" | (2''R'',3''R'')-tartaric acid <br/> (''R'',''R'')-tartaric acid <br/> (+)-tartaric acid <br/> ''d''-tartaric acid <small>''(obsolete)''</small> <br/> {{sc|L}}-tartaric acid <br/> {{sc|L}}-threaric acid <br/>("natural isomer")<ref>{{Cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/L-tartaric_acid |title=L-(+)-Tartaric acid |website=[[PubChem]] | | style="vertical-align:top" | (2''R'',3''R'')-tartaric acid <br/> (''R'',''R'')-tartaric acid <br/> (+)-tartaric acid <br/> ''d''-tartaric acid <small>''(obsolete)''</small> <br/> {{sc|L}}-tartaric acid <br/> {{sc|L}}-threaric acid <br/>("natural isomer")<ref>{{Cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/L-tartaric_acid |title=L-(+)-Tartaric acid |website=[[PubChem]] |archive-url=https://web.archive.org/web/20150516011103/https://pubchem.ncbi.nlm.nih.gov/compound/L-tartaric_acid#section=Top |archive-date=May 16, 2015}}</ref> | ||
| style="vertical-align:top" | (2''R'',3''S'')-tartaric acid <br/> ''meso''-tartaric acid <br/> erythraric acid | | style="vertical-align:top" | (2''R'',3''S'')-tartaric acid <br/> ''meso''-tartaric acid <br/> erythraric acid | ||
| style="vertical-align:top" | ''rac''-(2''R'',3''S'')-tartaric acid <br/> (2''RS'',3''SR'')-tartaric acid <br/> (±)-tartaric acid <br/> {{sc|DL}}-tartaric acid <br/> ''dl''-tartaric acid <small>''(obsolete)''</small> <br/> paratartaric acid <br/> uvic acid | | style="vertical-align:top" | ''rac''-(2''R'',3''S'')-tartaric acid <br/> (2''RS'',3''SR'')-tartaric acid <br/> (±)-tartaric acid <br/> {{sc|DL}}-tartaric acid <br/> ''dl''-tartaric acid <small>''(obsolete)''</small> <br/> paratartaric acid <br/> uvic acid | ||
| Line 185: | Line 185: | ||
==Reactivity== | ==Reactivity== | ||
L-(+)-tartaric acid, can participate in several reactions. As shown the reaction scheme below, | L-(+)-tartaric acid, can participate in several reactions. As shown the reaction scheme below, [[dihydroxymalonic acid]] is produced upon treatment of L-(+)-tartaric acid with hydrogen peroxide in the presence of a [[ferrous]] salt. | ||
:HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H + H<sub>2</sub>O<sub>2</sub> → HO<sub>2</sub>CC(OH)C(OH)CO<sub>2</sub>H + 2 H<sub>2</sub>O | :HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H + H<sub>2</sub>O<sub>2</sub> → HO<sub>2</sub>CC(OH)C(OH)CO<sub>2</sub>H + 2 H<sub>2</sub>O | ||
[[Dihydroxymaleic acid]] can then be oxidized to [[tartronic acid]] with nitric acid.<ref name=Blair>{{cite encyclopedia | last1 = Blair | first1 = G. T. | last2 = DeFraties | first2 = J. J. | title = Hydroxy Dicarboxylic Acids | encyclopedia = Kirk Othmer Encyclopedia of Chemical Technology | year = 2000 | pages = 1–19 | doi = 10.1002/0471238961.0825041802120109.a01 | isbn = | [[Dihydroxymaleic acid]] can then be oxidized to [[tartronic acid]] with nitric acid.<ref name=Blair>{{cite encyclopedia | last1 = Blair | first1 = G. T. | last2 = DeFraties | first2 = J. J. | title = Hydroxy Dicarboxylic Acids | encyclopedia = Kirk Othmer Encyclopedia of Chemical Technology | year = 2000 | pages = 1–19 | doi = 10.1002/0471238961.0825041802120109.a01 | isbn = 0-471-23896-1 }}</ref> | ||
==Derivatives==<!-- This section is linked from [[Napoleon I of France]] --> | ==Derivatives==<!-- This section is linked from [[Napoleon I of France]] --> | ||
| Line 223: | Line 223: | ||
== Toxicity in dogs == | == Toxicity in dogs == | ||
While tartaric acid is well-tolerated by humans and lab animals, an April 2021 letter to the editor of ''[[Journal of the American Veterinary Medical Association|JAVMA]]'' hypothesized that the tartaric acid in grapes could be the cause of [[grape and raisin toxicity in dogs]]. Two cases of | While tartaric acid is well-tolerated by humans and lab animals, an April 2021 letter to the editor of ''[[Journal of the American Veterinary Medical Association|JAVMA]]'' hypothesized that the tartaric acid in grapes could be the cause of [[grape and raisin toxicity in dogs]]. Two cases of ingestion of [[cream of tartar]] caused a similar toxic reaction, with similar symptoms of [[acute kidney injury]] and (in one case) similar histological findings in the kidneys at autopsy.<ref>{{Cite web|url=https://www.aaha.org/publications/newstat/articles/2021-04/what-causes-grape-toxicity-in-dogs-playdough-might-have-led-to-a-breakthrough/|title=What causes grape toxicity in dogs? Playdough might have led to a breakthrough|website=American Animal Hospital Association|first=Tony|last=McReynolds|date=April 1, 2021|archive-url=https://web.archive.org/web/20210419032534/https://www.aaha.org/publications/newstat/articles/2021-04/what-causes-grape-toxicity-in-dogs-playdough-might-have-led-to-a-breakthrough|archive-date=19 April 2021|access-date=13 July 2021|url-status=live}}</ref><ref>{{cite journal |vauthors=Wegenast C, Meadows I, Anderson R, Southard T | title=Unique sensitivity of dogs to tartaric acid and implications for toxicity of grapes (Letters to the Editor) | journal=Journal of the American Veterinary Medical Association | publisher=American Veterinary Medical Association (AVMA) | volume=258 | issue=7 | date=2021-04-01 | issn=0003-1488 | doi=10.2460/javma.258.7.704 | pages=704–707| pmid=33754816 }}</ref> | ||
A 2022 article expands on the letter with detailed reports of the 2 aforementioned cases of cream of tartar ingestion and 4 new cases of [[tamarind]] ingestion. Again, clinical findings were similar. Tamarind is known to contain 8%–18% tartaric acid, much more than the up to 2% (typically 0.35%–1.1%) found in grapes. The authors believe that the assignment of tartaric acid as the culprit also explains the relative lack of incidents from dogs consuming commercial grape juice, jam, and wine, as these go through a process to remove tartrates.<ref>{{cite journal |last1=Wegenast |first1=CA |title=Acute kidney injury in dogs following ingestion of cream of tartar and tamarinds and the connection to tartaric acid as the proposed toxic principle in grapes and raisins |journal=J Vet Emerg Crit Care |date=2022 |volume=32 |issue=6 |pages=812–816 |doi=10.1111/vec.13234|pmid=35869755 |s2cid=250989489 }}</ref> | A 2022 article expands on the letter with detailed reports of the 2 aforementioned cases of cream of tartar ingestion and 4 new cases of [[tamarind]] ingestion. Again, clinical findings were similar. Tamarind is known to contain 8%–18% tartaric acid, much more than the up to 2% (typically 0.35%–1.1%) found in grapes. The authors believe that the assignment of tartaric acid as the culprit also explains the relative lack of incidents from dogs consuming commercial grape juice, jam, and wine, as these go through a process to remove tartrates.<ref>{{cite journal |last1=Wegenast |first1=CA |title=Acute kidney injury in dogs following ingestion of cream of tartar and tamarinds and the connection to tartaric acid as the proposed toxic principle in grapes and raisins |journal=J Vet Emerg Crit Care |date=2022 |volume=32 |issue=6 |pages=812–816 |doi=10.1111/vec.13234|pmid=35869755 |s2cid=250989489 }}</ref> | ||
A 2023 study | A 2023 study observed tartaric acid toxicity in kidney cells of dogs, but not in human kidney cells.<ref>{{cite journal | last1=Coyne | first1=Sean R. | last2=Landry | first2=Greg M. | title=Tartaric acid induces toxicity in Madin–Darby canine kidney cells, but not human kidney-2 cells in vitro, and is prevented by organic anion transporter inhibition and human OAT-4 transfection | journal=Journal of Veterinary Emergency and Critical Care | volume=33 | issue=3 | date=2023 | issn=1479-3261 | doi=10.1111/vec.13294 | pages=298–304| pmid=37087614 }}</ref> | ||
A 2024 review identified a relationship between grape ingestion and illness, though the specific type or quantity of grapes that cause toxicity remains unclear. Grape ingestion commonly leads to gastrointestinal and/or renal issues, with treatment depending on the symptoms; outcomes can vary.<ref>{{cite journal | last1=Downs | first1=Joshua | last2=Zoltowska | first2=Agnieszka | last3=Hackney | first3=Thomas | last4=Gardner | first4=David S. | last5=Ashmore | first5=Alison | last6=Brennan | first6=Marnie L. | title=Scoping review exploring the evidence base on Vitis vinifera toxicity in dogs after ingestion: Clinical effects, treatments and types of V. vinifera | journal=Veterinary Record | volume=195 | issue=7 | date=2024-10-05 | | A 2024 review identified a relationship between grape ingestion and illness in dogs, though the specific type or quantity of grapes that cause toxicity remains unclear. Grape ingestion commonly leads to gastrointestinal and/or renal issues, with treatment depending on the symptoms; outcomes can vary.<ref>{{cite journal | last1=Downs | first1=Joshua | last2=Zoltowska | first2=Agnieszka | last3=Hackney | first3=Thomas | last4=Gardner | first4=David S. | last5=Ashmore | first5=Alison | last6=Brennan | first6=Marnie L. | title=Scoping review exploring the evidence base on Vitis vinifera toxicity in dogs after ingestion: Clinical effects, treatments and types of V. vinifera | journal=Veterinary Record | volume=195 | issue=7 | date=2024-10-05 | article-number=e4536 | issn=0042-4900 | doi=10.1002/vetr.4536 | doi-access=free | pmid=39183495 }}</ref> | ||
==References== | ==References== | ||
| Line 247: | Line 247: | ||
[[Category:Food acidity regulators]] | [[Category:Food acidity regulators]] | ||
[[Category:Acids in wine]] | [[Category:Acids in wine]] | ||
[[Category:Alpha | [[Category:Alpha hydroxycarboxylic acids]] | ||
[[Category:Dicarboxylic acids]] | [[Category:Dicarboxylic acids]] | ||
[[Category:Vicinal diols]] | [[Category:Vicinal diols]] | ||
[[Category:E-number additives]] | [[Category:E-number additives]] | ||
Revision as of 11:35, 26 October 2025
Template:Short description <templatestyles src="Chembox/styles.css"/>
Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox ConjugateAcidBaseTemplate:Chembox HazardsTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:YesnoTemplate:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description
Script error: No such module "Distinguish".
Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus.[1] Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. Potassium bitartrate is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation. The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste. Naturally occurring tartaric acid is a useful raw material in organic synthesis. Tartaric acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics and is a dihydroxyl derivative of succinic acid.
History
Tartaric acid has been known to winemakers for centuries– its crude crystalline form as found off top of wine barrels were called Template:Wikt-lang (rendered tartre by Chaucer) or "wine stone".[6] However, chemical extraction and purification was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele.[7]
Tartaric acid played an important role in the discovery of chemical chirality. This property of tartaric acid was first observed in 1832 by Jean Baptiste Biot, who observed its ability to rotate polarized light.[8][9] Louis Pasteur continued this research in 1847 by investigating the shapes of sodium ammonium tartrate crystals, which he found to be chiral. By manually sorting the differently shaped crystals, Pasteur was the first to produce a pure sample of levotartaric acid.[10][11][12][13][14]
Stereochemistry
<templatestyles src="Stack/styles.css"/>
Script error: No such module "Check for unknown parameters".
Naturally occurring form of the acid is dextro tartaric acid or L-(+)-tartaric acid (obsolete name d-tartaric acid). Because it is available naturally, it is cheaper than its enantiomer and the meso isomer. The dextro and levo prefixes are archaic terms.[15] Modern textbooks refer to the natural form as (2R,3R)-tartaric acid (L-(+)-tartaric acid), and its enantiomer as (2S,3S)-tartaric acid (D-(−)-tartaric acid). The meso diastereomer is referred to as (2R,3S)-tartaric acid or (2S,3R)-tartaric acid.
- Dextro and levo form monoclinic sphenoidal crystals[16] and orthorhombic crystals.
- Racemic tartaric acid forms monoclinic[17] and triclinic crystals (space group P1).[18][19]
- Anhydrous meso tartaric acid form two anhydrous polymorphs: triclinic and orthorhombic.
- Monohydrated meso tartaric acid crystallizes as monoclinic and triclinic polymorphys depending on the temperature at which crystallization from aqueous solution occurs.[20]
Tartaric acid in Fehling's solution binds to copper(II) ions, preventing the formation of insoluble hydroxide salts.
| DL-tartaric acid (racemic acid) (when in 1:1 ratio) | mesotartaric acid | |
|---|---|---|
| dextrotartaric acid (L-(+)-tartaric acid) |
levotartaric acid (D-(−)-tartaric acid) | |
| File:L-tartaric acid.svg | File:D-tartaric acid.svg | File:Meso-Weinsäure Spiegel.svg |
| Common name | Tartaric acid | Levotartaric acid | Dextrotartaric acid | Mesotartaric acid | Racemic acid |
|---|---|---|---|---|---|
| Synonyms | (2S,3S)-tartaric acid (S,S)-tartaric acid (−)-tartaric acid l-tartaric acid (obsolete) levotartaric acid Template:Sc-tartaric acid Template:Sc-threaric acid ("unnatural isomer")[21] |
(2R,3R)-tartaric acid (R,R)-tartaric acid (+)-tartaric acid d-tartaric acid (obsolete) Template:Sc-tartaric acid Template:Sc-threaric acid ("natural isomer")[22] |
(2R,3S)-tartaric acid meso-tartaric acid erythraric acid |
rac-(2R,3S)-tartaric acid (2RS,3SR)-tartaric acid (±)-tartaric acid Template:Sc-tartaric acid dl-tartaric acid (obsolete) paratartaric acid uvic acid | |
| PubChem | CID 875 from PubChemTemplate:EditAtWikidataTemplate:WikidataCheck | CID 439655 from PubChemTemplate:EditAtWikidataTemplate:WikidataCheck | CID 444305 from PubChemTemplate:EditAtWikidataTemplate:WikidataCheck | CID 78956 from PubChemTemplate:EditAtWikidataTemplate:WikidataCheck | CID 5851 from PubChemTemplate:EditAtWikidataTemplate:WikidataCheck |
| EINECS number | |||||
| CAS number | 526-83-0 | 147-71-7 | 87-69-4 | 147-73-9 | 133-37-9 |
Production
L-(+)-Tartaric acid
The L-(+)-tartaric acid isomer of tartaric acid is industrially produced in the largest amounts. It is obtained from lees, a solid byproduct of fermentations. The former byproducts mostly consist of potassium bitartrate (Template:Chem2). This potassium salt is converted to calcium tartrate (Template:Chem2) upon treatment with calcium hydroxide (Template:Chem2):[23]
In practice, higher yields of calcium tartrate are obtained with the addition of calcium sulfate. Calcium tartrate is then converted to tartaric acid by treating the salt with aqueous sulfuric acid:
Racemic tartaric acid
Racemic tartaric acid can be prepared in a multistep reaction from maleic acid. In the first step, the maleic acid is epoxidized by hydrogen peroxide using Template:Ill as a catalyst.[23]
In the next step, the epoxide is hydrolyzed.
meso-Tartaric acid
A mixture of racemic acid and meso-tartaric acid is formed when dextro-Tartaric acid is heated in water at 165 °C for about 2 days. meso-Tartaric acid can also be prepared from dibromosuccinic acid using silver hydroxide:[24]
meso-Tartaric acid can be separated from residual racemic acid by crystallization, the racemate being less soluble.
Reactivity
L-(+)-tartaric acid, can participate in several reactions. As shown the reaction scheme below, dihydroxymalonic acid is produced upon treatment of L-(+)-tartaric acid with hydrogen peroxide in the presence of a ferrous salt.
- HO2CCH(OH)CH(OH)CO2H + H2O2 → HO2CC(OH)C(OH)CO2H + 2 H2O
Dihydroxymaleic acid can then be oxidized to tartronic acid with nitric acid.[25]
Derivatives
Important derivatives of tartaric acid include:
- Sodium ammonium tartrate, the first material separated into its enantiomers
- cream of tartar (potassium bitartrate), used in cooking
- Rochelle salt (potassium sodium tartrate), which has unusual piezoelectric properties
- tartar emetic (antimony potassium tartrate), a resolving agent.[26][27][28] Diisopropyl tartrate is used as a co-catalyst in asymmetric synthesis.
Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.[29] The median lethal dose (LD50) is about 7.5 grams/kg for a human, 5.3 grams/kg for rabbits, and 4.4 grams/kg for mice.[30] Given this figure, it would take over Script error: No such module "convert". to kill a person weighing Script error: No such module "convert". with 50% probability, so it may be safely included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334; tartrates are other additives serving as antioxidants or emulsifiers.
When cream of tartar is added to water, a suspension results which serves to clean copper coins very well, as the tartrate solution can dissolve the layer of copper(II) oxide present on the surface of the coin. The resulting copper(II)-tartrate complex is easily soluble in water.
Tartaric acid in wine
Script error: No such module "Labelled list hatnote".Script error: No such module "Unsubst".
Tartaric acid may be most immediately recognizable to wine drinkers as the source of "wine diamonds", the small potassium bitartrate crystals that sometimes form spontaneously on the cork or bottom of the bottle. These "tartrates" are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through cold stabilization (which is not always preferred since it can change the wine's profile). The tartrates remaining on the inside of aging barrels were at one time a major industrial source of potassium bitartrate.
Tartaric acid plays an important role chemically, lowering the pH of fermenting "must" to a level where many undesirable spoilage bacteria cannot live, and acting as a preservative after fermentation. In the mouth, tartaric acid provides some of the tartness in the wine, although citric and malic acids also play a role.
Tartaric acid in fruits
Grapes and tamarinds have the highest levels of tartaric acid concentration. Other fruits with tartaric acid are bananas, avocados, prickly pear fruit, apples, cherries, papayas, peaches, pears, pineapples, strawberries, mangoes and citrus fruits.[1][31]
Trace amounts of tartaric acid have been found in cranberries and other berries.[32]
Tartaric acid is also present in the leaves and pods of Pelargonium plants and beans.
Applications
Tartaric acid and its derivatives have a plethora of uses in the field of pharmaceuticals. For example, it has been used in the production of effervescent salts, in combination with citric acid, to improve the taste of oral medications.[25] The potassium antimonyl derivative of the acid known as tartar emetic is included, in small doses, in cough syrup as an expectorant.
Tartaric acid also has several applications for industrial use. The acid has been observed to chelate metal ions such as calcium and magnesium. Therefore, the acid has served in the farming and metal industries as a chelating agent for complexing micronutrients in soil fertilizer and for cleaning metal surfaces consisting of aluminium, copper, iron, and alloys of these metals, respectively.[23]
Toxicity in dogs
While tartaric acid is well-tolerated by humans and lab animals, an April 2021 letter to the editor of JAVMA hypothesized that the tartaric acid in grapes could be the cause of grape and raisin toxicity in dogs. Two cases of ingestion of cream of tartar caused a similar toxic reaction, with similar symptoms of acute kidney injury and (in one case) similar histological findings in the kidneys at autopsy.[33][34]
A 2022 article expands on the letter with detailed reports of the 2 aforementioned cases of cream of tartar ingestion and 4 new cases of tamarind ingestion. Again, clinical findings were similar. Tamarind is known to contain 8%–18% tartaric acid, much more than the up to 2% (typically 0.35%–1.1%) found in grapes. The authors believe that the assignment of tartaric acid as the culprit also explains the relative lack of incidents from dogs consuming commercial grape juice, jam, and wine, as these go through a process to remove tartrates.[35]
A 2023 study observed tartaric acid toxicity in kidney cells of dogs, but not in human kidney cells.[36]
A 2024 review identified a relationship between grape ingestion and illness in dogs, though the specific type or quantity of grapes that cause toxicity remains unclear. Grape ingestion commonly leads to gastrointestinal and/or renal issues, with treatment depending on the symptoms; outcomes can vary.[37]
References
<templatestyles src="Reflist/styles.css" />
- ↑ a b c Tartaric Acid – Compound Summary, PubChem.
- ↑ Script error: No such module "citation/CS1".
- ↑ In the older literature, there is confusion about the use of D and L in the case of tartaric acids. It is therefore recommended to use the R,S system in this case.
- ↑ Script error: No such module "citation/CS1".
- ↑ Dawson, R.M.C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
- ↑ Script error: No such module "citation/CS1".
- ↑ Retzius, Anders Jahan (1770) "Försök med vinsten och dess syra" (Experiments with cream of tartar and its acid), Kungliga Vetenskapsakademiens Handlingar (Proceedings of the Royal Academy of Sciences), 31 : 207–213. From p. 209: "§. 6. Dessa försök omtalte jag för Hr. Carl Wilhelm Scheele (en snabb och lårgirug Pharmaciæ Studiosus) … " (§. 6. I mention these experiments on behalf of Mr. Carl Wilhelm Scheele (a quick and studious student of pharmacology) … )
- ↑ Biot (1835) "Mémoire sur la polarization circulaire et sur ses applications à la chimie organique" (Memoir on circular polarization and on its applications to organic chemistry), Mémoires de l'Académie des sciences de l'Institut, 2nd series, 13 : 39–175. That tartaric acid (acide tartarique cristallisé) rotates plane-polarized light is shown in Table G following p. 168. (Note: This article was read to the French Royal Academy of Sciences on 1832 November 5.)
- ↑ Biot (1838) "Pour discerner les mélanges et les combinaisons chimiques définies ou non définies, qui agissent sur la lumière polarisée; suivies d'applications aux combinaisons de l'acide tartarique avec l'eau, l'alcool et l'esprit de bois" (In order to discern mixtures and chemical combinations, defined or undefined, which act on polarized light; followed by applications to combinations of tartaric acid with water, alcohol [i.e., ethanol], and spirit of wood [i.e., methanol]), Mémoires de l'Académie des sciences de l'Institut, 2nd series, 15 : 93–279.
- ↑ Script error: No such module "Citation/CS1".
- ↑ L. Pasteur (1848) "Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire" (On the relations that can exist between crystalline form, and chemical composition, and the sense of rotary polarization), Annales de Chimie et de Physique, 3rd series, 24 : 442–459.
- ↑ Pasteur, Louis (1850) "Recherches sur les propriétés spécifiques des deux acides qui composent l'acide racémique" [Investigations into the specific properties of the two acids that compose racemic acid], Annales de Chimie et de Physique, 3rd series, 28 (3) : 56–99. See also Plate II. (See also the report of the commission that was appointed to verify Pasteur's findings, pp. 99–117.) [in French]
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1"., based on P. Groth's "Chemische Krystallographie".
- ↑ CRC Handbook of Chemistry and Physics, 49th edition.
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1"., Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ a b c J.-M. Kassaian "Tartaric acid" in Ullmann's Encyclopedia of Industrial Chemistry; VCH: Weinheim, Germany, 2002, 35, 671-678. Script error: No such module "CS1 identifiers".
- ↑ Augustus Price West. Experimental Organic Chemistry. World Book Company: New York, 1920, 232-237.
- ↑ a b Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ J.B. Gurtler, T.L. Mai, in Encyclopedia of Food Microbiology (Second Edition), 2014. PRESERVATIVES | Traditional Preservatives – Organic Acids: Tartaric Acid.
- ↑ Phytochemicals of Cranberries and Cranberry Products: Characterization, Potential Health Effects, and Processing Stability https://www.researchgate.net/publication/44573816_Phytochemicals_of_Cranberries_and_Cranberry_Products_Characterization_Potential_Health_Effects_and_Processing_Stability
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
Script error: No such module "Check for unknown parameters".
External links
Script error: No such module "Side box".