Thymol (YMDB16087)

Identification

YMDB ID

YMDB16087

Name

Thymol

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Thymol is a phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. (Dorland, 28th ed) -- Pubchem; Thymol is a monoterpene phenol derivative of cymene, C10H13OH, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. It is also called "hydroxy cymene". (from Webster's 1913 dictionary) -- Wikipedia; In a 1994 report released by five top cigarette companies, thymol is one of the 599 additives to cigarettes. Its use or purpose, however, is unknown, like most cigarette additives. -- Wikipedia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-Hydroxy-5-methyl-2-isopropylbenzene
2-Isopropyl-5-methylphenol
3-p-Cymenol
5-METHYL-2-(1-methylethyl)phenol
5-Methyl-2-isopropylphenol
6-Isopropyl-3-methylphenol
6-Isopropyl-m-cresol
1-Methyl-3-hydroxy-4-isopropylbenzene
2-Hydroxy-1-isopropyl-4-methylbenzene
3-Hydroxy-1-methyl-4-isopropylbenzene
3-Hydroxy-P-cymene
3-Methyl-6-isopropylphenol
5-Methyl-2-isopropyl-1-phenol
6-Isopropyl-P-cresol
Isopropyl cresol
Isopropyl-m-cresol
m-Thymol
P-Cymen-3-ol
Thymate
Thyme camphor
Thymic acid
Thymol crystal puriss
Thymol swarm brand
Apiguard
Swarm brand OF thymol

CAS number

Not Available

Weight

Average: 150.221
Monoisotopic: 150.104465071

InChI Key

MGSRCZKZVOBKFT-UHFFFAOYSA-N

InChI

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3

IUPAC Name

5-methyl-2-(propan-2-yl)phenol

Traditional IUPAC Name

thymol

Chemical Formula

C₁₀H₁₄O

SMILES

CC(C)C1=C(O)C=C(C)C=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Cumene
Phenylpropane
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Benzenoid
Monocyclic benzene moiety
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:27607 )
monoterpenoid (CHEBI:27607 )
Menthane monoterpenoids (C09908 )
Cyclic monoterpenes (C09908 )
Menthane monoterpenoids (LMPR0102090029 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.43	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.59	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.27 m³·mol⁻¹	ChemAxon
Polarizability	17.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Camphor	FDB014795
Herbal	FDB014795
Medicinal	FDB014795
Phenolic	FDB014795
Thyme	FDB014795

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0900000000-333dc57384e65e3b4cfa	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-1900000000-3679938a5ea114a30e48	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-3900000000-8ce5865e48dad7250d5e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-0109030000-5562c203cb318f30321b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-2492200000-85342d698be72263a95f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0900000000-333dc57384e65e3b4cfa	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-1900000000-3679938a5ea114a30e48	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-3900000000-8ce5865e48dad7250d5e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-0109030000-5562c203cb318f30321b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-2492200000-85342d698be72263a95f	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-3900000000-e309fdc1ab0cd926b420	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9880000000-3a69bebdbca0f95e862a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01p9-9700000000-e1a28495617d7b014e5c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9300000000-baeee6cdcafaadeebdec	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-015c-9100000000-e1efa41eaf818832448a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-000i-0900000000-333dc57384e65e3b4cfa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-000i-1900000000-3679938a5ea114a30e48	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-000i-3900000000-f72f603d97f0f7081b8d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 10V, negative	splash10-0002-0900000000-d3ae016121d86e17ddb4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 13V, negative	splash10-0002-1900000000-3e340243a54a9e3f0da4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 19V, negative	splash10-00dm-8900000000-82e846f2a3546e27414c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0002-0900000000-844f0c545c66f6c63993	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, negative	splash10-0a4i-0900000000-d30a5d305446b3540d85	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2900000000-4e6c9c70215576f53b60	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-2900000000-eeb06bc7587fcef0ba86	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-a8236f8b0194b3d08844	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-be4566e335ee9b00c724	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-fde7d3d2a42203ba2b95	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-92d1da1fba9df31389ed	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-32e3f430e6dfc819272b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2900000000-19305d290c7303afc3f5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pw9-7900000000-b0fcecf9ea71d3528408	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1b21dedfdc78e416ea8f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-43b3e1a99ba193849bf4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0532-3900000000-a152936b0bcf0d320092	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-9800000000-947167dd66d5b6947416	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9600000000-df6822dada158a51482c	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-000i-4900000000-73edaa628c1f5f2e1bd9	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Robinson AL, Ebeler SE, Heymann H, Boss PK, Solomon PS, Trengove RD. (2009). "Interactions between wine volatile compounds and grape and wine matrix components influence aroma compound headspace partitioning." J Agric Food Chem. 2009 Nov 11;57(21):10313-22.19845354

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	27607
HMDB ID	HMDB0001878
Pubchem Compound ID	6989
Kegg ID	C09908
ChemSpider ID	21105998
FOODB ID	FDB014795
Wikipedia ID	Thymol
BioCyc ID	Not Available

Structure for #<Compound:0xa0db6910>