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{{short description|Chemical compound found in plants including thyme}} | {{short description|Chemical compound found in plants including thyme}} | ||
{{Distinguish|Melitracen{{!}}Thymeol|Thymine|Thiamine}} | {{Distinguish|Melitracen{{!}}Thymeol|Thymine|Thiamine}} | ||
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{{Use dmy dates|date=November 2020}} | {{Use dmy dates|date=November 2020}} | ||
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'''Thymol''' (also known as '''2-isopropyl-5-methylphenol''', IPMP), {{chem2|C10H14O}}, is a | '''Thymol''' (also known as '''2-isopropyl-5-methylphenol''', IPMP), {{chem2|C10H14O}}, is a [[Monoterpene|monoterpenoid]], [[Phenols|phenol]] derivative of [[p-Cymene|''p''-cymene]], [[isomer]]ic with [[carvacrol]].<ref name="pubchem">{{cite web |title=Thymol |url=https://pubchem.ncbi.nlm.nih.gov/compound/6989 |publisher=PubChem, US National Library of Medicine |access-date=28 June 2025 |date=21 June 2025}}</ref> It occurs naturally in the oil of [[thyme]], and it is [[Liquid–liquid extraction|extracted]] from ''[[Thymus vulgaris]]'' (common thyme), [[ajwain]],<ref>{{Cite book|title=The book of spice: from anise to zedoary|last=O'Connell, John |date=27 August 2019 |isbn=978-1681774459 |publisher=Pegasus |location=New York |oclc=959875923}}</ref> and various other plants as a white [[crystal|crystalline]] substance of a pleasant [[Aromaticity|aromatic]] [[odor]].<ref name=pubchem/> | ||
Thymol provides the distinctive flavor of the [[Herb|culinary herb]] thyme, also produced from ''T. vulgaris''.<ref name=pubchem/> Thymol is only slightly [[solubility|soluble]] in water at neutral [[pH]], but is highly soluble in [[Alcohol (chemistry)|alcohol]]s, other organic solvents, and in strongly [[alkali]]ne aqueous solutions due to [[deprotonation]] of the [[phenol]]. | |||
== Chemical synthesis == | == Chemical synthesis == | ||
Thymol is produced by the [[alkylation]] of [[M-Cresol|''m''-cresol]] and [[propene]] | Thymol is produced by the [[alkylation]] of [[M-Cresol|''m''-cresol]] and [[propene]].<ref>{{cite book|last1=Stroh|first1=R.|last2=Sydel|first2=R.|last3=Hahn|first3=W.|editor1-last=Foerst|editor1-first=Wilhelm|title=Newer Methods of Preparative Organic Chemistry, Volume 2|date=December 2012|publisher=Academic Press|location=New York|isbn=9780323150422|page=344|edition= 1st|url=https://books.google.com/books?id=LG2J6i1sUAMC&pg=PA344}}</ref><ref>{{Ullmann |doi=10.1002/14356007.a19_313|title=Phenol Derivatives |year=2000 |last1=Fiege |first1=Helmut |last2=Voges |first2=Heinz-Werner |last3=Hamamoto |first3=Toshikazu |last4=Umemura |first4=Sumio |last5=Iwata |first5=Tadao |last6=Miki |first6=Hisaya |last7=Fujita |first7=Yasuhiro |last8=Buysch |first8=Hans-Josef |last9=Garbe |first9=Dorothea |last10=Paulus |first10=Wilfried |isbn=3527306730 }}</ref> | ||
{{chem2|CH3C6H4OH + CH2CHCH3 -> ((CH3)2CH)CH3C6H3OH}} | |||
A predicted method of biosynthesis of thymol in thyme and oregano begins with the cyclization of geranyl diphosphate by TvTPS2 to γ-terpinene. Oxidation by a [[cytochrome P450]] in the CYP71D subfamily creates a [[dienol]] intermediate, which is then converted into a ketone by short-chain dehydrogenase. Lastly, [[keto-enol tautomerization]] gives thymol. Its dissociation constant ([[pKa|p''K''<sub>a</sub>]]) is {{val|10.59|0.10}}.<ref>CAS Registry: Data obtained from SciFinder{{full citation needed|date=August 2017}}</ref> Thymol absorbs maximum [[ultraviolet|UV]] radiation at 274 nm.<ref>{{cite journal | last1 = Norwitz | first1 = G. | last2 = Nataro | first2 = N. | last3 = Keliher | first3 = P. N. | year = 1986 | title = Study of the Steam Distillation of Phenolic Compounds Using Ultraviolent Spectrometry | journal = Anal. Chem. | volume = 58 | issue = 639–640| page = 641 | doi = 10.1021/ac00294a034 }}</ref> | |||
==History== | ==History== | ||
The bee balms ''[[Monarda fistulosa]]'' and ''[[Monarda didyma]]'', North American wildflowers, are natural sources of thymol. The [[Blackfoot]] Native Americans recognized these plants' strong [[antiseptic]] action and used [[poultice]]s of the plants for skin [[infection]]s and minor [[wound]]s. A [[tisane]] made from them was also used to treat mouth and throat [[infection]]s caused by dental [[caries]] and [[gingivitis]].<ref>{{cite book|last=Tilford |first=Gregory L. |date=1997 |title=Edible and Medicinal Plants of the West |location=Missoula, MT |publisher=Mountain Press Publishing |isbn=978-0-87842-359-0}}</ref> | The bee balms ''[[Monarda fistulosa]]'' and ''[[Monarda didyma]]'', North American wildflowers, are natural sources of thymol. The [[Blackfoot]] Native Americans recognized these plants' strong [[antiseptic]] action and used [[poultice]]s of the plants for skin [[infection]]s and minor [[wound]]s. A [[tisane]] made from them was also used to treat mouth and throat [[infection]]s caused by dental [[caries]] and [[gingivitis]].<ref>{{cite book|last=Tilford |first=Gregory L. |date=1997 |title=Edible and Medicinal Plants of the West |location=Missoula, MT |publisher=Mountain Press Publishing |isbn=978-0-87842-359-0}}</ref> | ||
Thymol was first isolated by German chemist [[Caspar Neumann (chemist)|Caspar Neumann]] in 1719.<ref>{{cite journal|first=Carolo |last=Neuman |date=1724 |title=De Camphora |journal=Philosophical Transactions of the Royal Society of London |volume=33 |issue=389 |pages=321–332 |url=http://rstl.royalsocietypublishing.org/content/33/381-391/321.full.pdf+html |doi=10.1098/rstl.1724.0061|doi-access=free |url-access=subscription }} On page 324, Neumann mentions that in 1719 he distilled some essential oils from various herbs. On page 326, he mentions that during these experiments, he obtained a crystalline substance from thyme oil, which he called "''Camphora Thymi''" ([[camphor]] of thyme). (Neumann gave the name "camphor" not only to the specific substance that today is called camphor but to any crystalline substance that precipitated from a volatile, fragrant oil from some plant.)</ref> In 1853, French chemist Alexandre Lallemand<ref>Marie-Étienne-Alexandre Lallemand (December 25, 1816 - March 16, 1886)</ref> (1816-1886) named thymol and determined its empirical formula.<ref>{{cite journal|first=A. |last=Lallemand |date=1853 |url=http://gallica.bnf.fr/ark:/12148/bpt6k29948/f502.image.langEN |title=Sur la composition de l'huile essentielle de thym |trans-title=On the composition of the essential oil of thyme |language=fr |journal=Comptes Rendus |volume=37 |pages=498–500}}</ref> [[ | Thymol was first isolated by German chemist [[Caspar Neumann (chemist)|Caspar Neumann]] in 1719.<ref>{{cite journal|first=Carolo |last=Neuman |date=1724 |title=De Camphora |journal=Philosophical Transactions of the Royal Society of London |volume=33 |issue=389 |pages=321–332 |url=http://rstl.royalsocietypublishing.org/content/33/381-391/321.full.pdf+html |doi=10.1098/rstl.1724.0061|doi-access=free |url-access=subscription }} On page 324, Neumann mentions that in 1719 he distilled some essential oils from various herbs. On page 326, he mentions that during these experiments, he obtained a crystalline substance from thyme oil, which he called "''Camphora Thymi''" ([[camphor]] of thyme). (Neumann gave the name "camphor" not only to the specific substance that today is called camphor but to any crystalline substance that precipitated from a volatile, fragrant oil from some plant.)</ref> In 1853, French chemist Alexandre Lallemand<ref>Marie-Étienne-Alexandre Lallemand (December 25, 1816 - March 16, 1886)</ref> (1816-1886) named thymol and determined its empirical formula.<ref>{{cite journal|first=A. |last=Lallemand |date=1853 |url=http://gallica.bnf.fr/ark:/12148/bpt6k29948/f502.image.langEN |title=Sur la composition de l'huile essentielle de thym |trans-title=On the composition of the essential oil of thyme |language=fr |journal=Comptes Rendus |volume=37 |pages=498–500}}</ref> Possible [[antiseptic]] properties of thymol were discovered in 1875,<ref>{{Cite book |last=Oettingen |first=Wolfgang Felix Von |url=https://books.google.com/books?id=reaUWvD-bhYC&pg=PA78 |title=Phenol and Its Derivatives: The Relation Between Their Chemical Constitution and Their Effect on the Organism |date=1949 |publisher=U.S. Government Printing Office |isbn= |language=en}}</ref> and it was first synthesized by Swedish chemist Oskar Widman (1852-1930) in 1882.<ref>{{cite journal|first=Oskar |last=Widmann |date=1882 |url=http://gallica.bnf.fr/ark:/12148/bpt6k90694n/f169.image.langEN |title=Ueber eine Synthese von Thymol aus Cuminol |trans-title=On a synthesis of thymol from cuminol |language=de |journal=Berichte der Deutschen Chemischen Gesellschaft zu Berlin |volume=15 |pages=166–172 |doi=10.1002/cber.18820150139}}</ref> | ||
==Extraction== | ==Extraction== | ||
The conventional method of [[extract]]ing is [[Hydrodistillation|hydro-distillation]] (HD), but can also be extracted with [[solvent]]-free [[microwave]] extraction (SFME). In 30 minutes, SFME yields similar amounts of thymol with more oxygenated compounds than 4.5 hours of hydro-distillation at atmospheric pressures without the need for solvent.<ref>{{Cite journal |last1=Lucchesi |first1=Marie E |last2=Chemat |first2=Farid |last3=Smadja |first3=Jacqueline |date=2004-07-23 |title=Solvent-free microwave extraction of essential oil from aromatic herbs: comparison with conventional hydro-distillation |url=https://www.sciencedirect.com/science/article/pii/S0021967304008672 |journal=Journal of Chromatography A |volume=1043 |issue=2 |pages=323–327 |doi=10.1016/j.chroma.2004.05.083 |pmid=15330107 |issn=0021-9673|url-access=subscription }}</ref> | The conventional method of [[extract]]ing is [[Hydrodistillation|hydro-distillation]] (HD), but can also be extracted with [[solvent]]-free [[microwave]] extraction (SFME). In 30 minutes, SFME yields similar amounts of thymol with more oxygenated compounds than 4.5 hours of hydro-distillation at atmospheric pressures without the need for solvent.<ref>{{Cite journal |last1=Lucchesi |first1=Marie E |last2=Chemat |first2=Farid |last3=Smadja |first3=Jacqueline |date=2004-07-23 |title=Solvent-free microwave extraction of essential oil from aromatic herbs: comparison with conventional hydro-distillation |url=https://www.sciencedirect.com/science/article/pii/S0021967304008672 |journal=Journal of Chromatography A |volume=1043 |issue=2 |pages=323–327 |doi=10.1016/j.chroma.2004.05.083 |pmid=15330107 |issn=0021-9673|url-access=subscription }}</ref> | ||
[[File:Thymol biosynthesis.svg|center|thumb|500px|Predicted biosynthesis of thymol in thyme and oregano. Reconstruction of figure 4 in Krause et. al. (2021).<ref name="r505">{{cite journal | last=Krause | first=Sandra T. | last2=Liao | first2=Pan | last3=Crocoll | first3=Christoph | last4=Boachon | first4=Benoît | last5=Förster | first5=Christiane | last6=Leidecker | first6=Franziska | last7=Wiese | first7=Natalie | last8=Zhao | first8=Dongyan | last9=Wood | first9=Joshua C. | last10=Buell | first10=C. Robin | last11=Gershenzon | first11=Jonathan | last12=Dudareva | first12=Natalia | last13=Degenhardt | first13=Jörg | title=The biosynthesis of thymol, carvacrol, and thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase | journal=Proceedings of the National Academy of Sciences | volume=118 | issue=52 | date=2021-12-28 | issn=0027-8424 | pmid=34930840 | pmc=8719858 | doi=10.1073/pnas.2110092118 | page=}}</ref>]] | |||
==Uses== | ==Uses== | ||
[[ | During the 1910s, thymol was used for [[hookworm infection]] in the United States.<ref>{{cite book|last=Ferrell|first=John Atkinson|title=The Rural School and Hookworm Disease|url=https://books.google.com/books?id=omYAAAAAYAAJ|series=US Bureau of Education Bulletin|volume=20, Whole No. 593|year=1914|publisher=U.S. Government Printing Office|location=Washington, DC}}</ref><ref name="Rosenau1913">{{cite book|surname=Milton|given=Joseph Rosenau|title=Preventive Medicine and Hygiene|url=https://books.google.com/books?id=mVfQAAAAMAAJ&pg=PA119|year=1913|publisher=D. Appleton|page=119}}</ref> People of the Middle East continue to use [[za'atar]], a delicacy made with large amounts of thyme, to reduce and eliminate internal parasites.<ref>{{Cite news|last1=Inskeep|first1=Steve|last2=Godoy|first2=Maria|date=2013-06-11|title=Za'atar: A Spice Mix With Biblical Roots And Brain Food Reputation|language=en|work=NPR|url=https://www.npr.org/sections/thesalt/2013/06/11/190672515/zaatar-a-spice-mix-with-biblical-roots-and-brain-food-reputation|access-date=2022-02-24}}</ref> It is also used as a [[preservative]] in [[halothane]], an [[anaesthetic]], and as an antiseptic in mouthwash. When used to reduce plaque and gingivitis, thymol has been found to be more effective when used in combination with [[chlorhexidine]] than when used purely by itself.<ref>{{cite journal | last1 = Filoche | first1 = S. K. | last2 = Soma | first2 = K. | last3 = Sissons | first3 = C. H. | year = 2005 | title = Antimicrobial effects of essential oils in combination with chlorhexidine digluconate | journal = Oral Microbiol. Immunol. | volume = 20 | issue = 4| pages = 221–225 | doi = 10.1111/j.1399-302X.2005.00216.x | pmid = 15943766 }}</ref> | ||
Thymol | Thymol is a fragrance ingredient in some [[cosmetics]].<ref name=pubchem/> Thymol has been used to successfully control [[varroa mite]]s and prevent fermentation and the growth of [[Mold (fungus)|mold]] in [[bees|bee colonies]].<ref name=bees>{{cite news|last=Ward |first=Mark |date=2006-03-08 |url=http://news.bbc.co.uk/2/hi/science/nature/4780034.stm |title=Almond farmers seek healthy bees |website=BBC News |publisher=BBC}}</ref> Thymol is also used as a rapidly degrading, non-persisting [[pesticide]],<ref name=pubchem/><ref name="J. Coats 2008" /> such as insecticides and fungicides which are leveraged in plant care products. Thymol can also be used as a medical disinfectant and general purpose [[disinfectant]].<ref>{{cite web|url=http://archive.epa.gov/pesticides/reregistration/web/pdf/3143fact.pdf|title=Thymol|publisher=US Environmental Protection Agency|date=September 1993}}</ref> Thymol is also used in the production of [[menthol]] through the hydrogenation of the aromatic ring.<ref>{{Cite web |date=2023-10-06 |title=Menthol {{!}} Definition, Structure, & Uses {{!}} Britannica |url=https://www.britannica.com/science/menthol |access-date=2023-10-30 |website=www.britannica.com |language=en}}</ref> | ||
==List of plants that contain thymol== | ==List of plants that contain thymol== | ||
{{div col|colwidth=10em}} | |||
* ''[[Illicium verum]]'' | * ''[[Illicium verum]]'' | ||
* ''[[Euphrasia rostkoviana]]''<ref>{{cite journal | pmid = 26000025 | doi=10.1155/2015/734101 | volume=2015 | title=Composition and Antimicrobial Activity of ''Euphrasia rostkoviana'' Hayne Essential Oil | pmc=4427012 | journal=Evid Based Complement Alternat Med | pages=1–5 | last1 = Novy | first1 = P. | last2 = Davidova | first2 = H. | last3 = Serrano Rojero | first3 = C. S. | last4 = Rondevaldova | first4 = J. | last5 = Pulkrabek | first5 = J. | last6 = Kokoska | first6 = L.| year=2015 | doi-access=free }}</ref> | * ''[[Euphrasia rostkoviana]]''<ref>{{cite journal | pmid = 26000025 | doi=10.1155/2015/734101 | volume=2015 | title=Composition and Antimicrobial Activity of ''Euphrasia rostkoviana'' Hayne Essential Oil | pmc=4427012 | journal=Evid Based Complement Alternat Med | pages=1–5 | last1 = Novy | first1 = P. | last2 = Davidova | first2 = H. | last3 = Serrano Rojero | first3 = C. S. | last4 = Rondevaldova | first4 = J. | last5 = Pulkrabek | first5 = J. | last6 = Kokoska | first6 = L.| year=2015 | doi-access=free }}</ref> | ||
| Line 250: | Line 253: | ||
| first4 = M. G.}}</ref> | | first4 = M. G.}}</ref> | ||
* ''[[Trachyspermum ammi]]'' | * ''[[Trachyspermum ammi]]'' | ||
{{div col end}} | |||
==Toxicology and environmental impacts== | ==Toxicology and environmental impacts== | ||
[[File:Thymolum by Danny S. - 001.JPG|thumb|200px|Thymol powder]] | |||
In 2009, the [[United States Environmental Protection Agency|U.S. Environmental Protection Agency (EPA)]] reviewed the research literature on the toxicology and environmental impact of thymol and concluded that "thymol has minimal potential toxicity and poses minimal risk".<ref>{{Federal Register|74|12613}}</ref> | In 2009, the [[United States Environmental Protection Agency|U.S. Environmental Protection Agency (EPA)]] reviewed the research literature on the toxicology and environmental impact of thymol and concluded that "thymol has minimal potential toxicity and poses minimal risk".<ref>{{Federal Register|74|12613}}</ref> | ||
Latest revision as of 23:16, 28 June 2025
Template:Short description Script error: No such module "Distinguish". Template:Use American English Template:Cs1 config Template:Use dmy dates Template:Chembox
Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), Template:Chem2, is a monoterpenoid, phenol derivative of p-cymene, isomeric with carvacrol.[1] It occurs naturally in the oil of thyme, and it is extracted from Thymus vulgaris (common thyme), ajwain,[2] and various other plants as a white crystalline substance of a pleasant aromatic odor.[1]
Thymol provides the distinctive flavor of the culinary herb thyme, also produced from T. vulgaris.[1] Thymol is only slightly soluble in water at neutral pH, but is highly soluble in alcohols, other organic solvents, and in strongly alkaline aqueous solutions due to deprotonation of the phenol.
Chemical synthesis
Thymol is produced by the alkylation of m-cresol and propene.[3][4] Template:Chem2
A predicted method of biosynthesis of thymol in thyme and oregano begins with the cyclization of geranyl diphosphate by TvTPS2 to γ-terpinene. Oxidation by a cytochrome P450 in the CYP71D subfamily creates a dienol intermediate, which is then converted into a ketone by short-chain dehydrogenase. Lastly, keto-enol tautomerization gives thymol. Its dissociation constant (pKa) is Template:Val.[5] Thymol absorbs maximum UV radiation at 274 nm.[6]
History
The bee balms Monarda fistulosa and Monarda didyma, North American wildflowers, are natural sources of thymol. The Blackfoot Native Americans recognized these plants' strong antiseptic action and used poultices of the plants for skin infections and minor wounds. A tisane made from them was also used to treat mouth and throat infections caused by dental caries and gingivitis.[7]
Thymol was first isolated by German chemist Caspar Neumann in 1719.[8] In 1853, French chemist Alexandre Lallemand[9] (1816-1886) named thymol and determined its empirical formula.[10] Possible antiseptic properties of thymol were discovered in 1875,[11] and it was first synthesized by Swedish chemist Oskar Widman (1852-1930) in 1882.[12]
Extraction
The conventional method of extracting is hydro-distillation (HD), but can also be extracted with solvent-free microwave extraction (SFME). In 30 minutes, SFME yields similar amounts of thymol with more oxygenated compounds than 4.5 hours of hydro-distillation at atmospheric pressures without the need for solvent.[13]
Uses
During the 1910s, thymol was used for hookworm infection in the United States.[15][16] People of the Middle East continue to use za'atar, a delicacy made with large amounts of thyme, to reduce and eliminate internal parasites.[17] It is also used as a preservative in halothane, an anaesthetic, and as an antiseptic in mouthwash. When used to reduce plaque and gingivitis, thymol has been found to be more effective when used in combination with chlorhexidine than when used purely by itself.[18]
Thymol is a fragrance ingredient in some cosmetics.[1] Thymol has been used to successfully control varroa mites and prevent fermentation and the growth of mold in bee colonies.[19] Thymol is also used as a rapidly degrading, non-persisting pesticide,[1][20] such as insecticides and fungicides which are leveraged in plant care products. Thymol can also be used as a medical disinfectant and general purpose disinfectant.[21] Thymol is also used in the production of menthol through the hydrogenation of the aromatic ring.[22]
List of plants that contain thymol
- Illicium verum
- Euphrasia rostkoviana[23]
- Lagoecia cuminoides[24]
- Monarda didyma[25]
- Monarda fistulosa[26]
- Mosla chinensis
- Ocimum gratissimum L.[27]
- Origanum compactum[28]
- Origanum dictamnus[29]
- Origanum onites[30][31]
- Origanum syriacum
- Origanum vulgare[32][33]
- Satureja hortensis
- Satureja thymbra
- Thymus glandulosus[28]
- Thymus hyemalis[34]
- Thymus serpyllum
- Thymus praecox
- Thymus vulgaris[34][35]
- Thymus zygis[36]
- Trachyspermum ammi
Toxicology and environmental impacts
In 2009, the U.S. Environmental Protection Agency (EPA) reviewed the research literature on the toxicology and environmental impact of thymol and concluded that "thymol has minimal potential toxicity and poses minimal risk".[37]
Environmental breakdown and use as a pesticide
Studies have shown that hydrocarbon monoterpenes and thymol in particular degrade rapidly (DT50 16 days in water, 5 days in soil[20]) in the environment and are, thus, low risks because of rapid dissipation and low bound residues,[20] supporting the use of thymol as a pesticide agent that offers a safe alternative to other more persistent chemical pesticides that can be dispersed in runoff and produce subsequent contamination. Though, there has been recent research into sustained released systems for botanically derived pesticides, such as using natural polysaccharides which would be biodegradable and biocompatible.[38]
Compendial status
See also
Notes and references
External links
Template:Commons category-inline
Template:GABAAR PAMs Template:Transient receptor potential channel modulators Template:Terpenoids
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- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1". On page 324, Neumann mentions that in 1719 he distilled some essential oils from various herbs. On page 326, he mentions that during these experiments, he obtained a crystalline substance from thyme oil, which he called "Camphora Thymi" (camphor of thyme). (Neumann gave the name "camphor" not only to the specific substance that today is called camphor but to any crystalline substance that precipitated from a volatile, fragrant oil from some plant.)
- ↑ Marie-Étienne-Alexandre Lallemand (December 25, 1816 - March 16, 1886)
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