Carvacrol (YMDB01647)

Identification

YMDB ID

YMDB01647

Name

Carvacrol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

5-Isopropyl-2-methylphenol, also known as 2-hydroxy-p-cymene or 2-methyl-5-isopropylphenol, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Thus, 5-isopropyl-2-methylphenol is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on 5-Isopropyl-2-methylphenol.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-Hydroxy-5-methyl-2-isopropylbenzene
1-Methyl-3-hydroxy-4-isopropylbenzene
2-Hydroxy-1-isopropyl-4-methylbenzene
2-Isopropyl-5-methylphenol
2-Isopropyl-5-methylphenol (thymol)
3-Hydroxy-1-methyl-4-isopropylbenzene
3-Hydroxy-p-cymene
3-Methyl-6-isopropylphenol
3-p-Cymenol
5-Methyl-2-(1-methylethyl)phenol
5-Methyl-2-isopropyl-1-phenol
5-Methyl-2-isopropylphenol
6-Isopropyl-3-methylphenol
6-Isopropyl-m-cresol
6-Isopropyl-p-cresol
Isopropyl cresol
Isopropyl-m-cresol
m-Cresol, 6-isopropyl-
m-Thymol
p-Cymen-3-ol
p-Cymene, 3-hydroxy-
Phenol, 2-isopropyl-5-methyl-
Phenol, 5-methyl-2-(1-methylethyl)-
Thymate
Thyme camphor
Thymic acid
Thymol
1-Hydroxy-2-methyl-5-isopropylbenzene
1-Methyl-2-hydroxy-4-isopropylbenzene
2-Hydroxy-p-cymene
2-Methyl-5-(1-methylethyl)phenol
2-Methyl-5-isopropylphenol
2-p-Cymenol
3-Isopropyl-6-methylphenol
5-Isopropyl-O-cresol
2-Hydroxy-4-isopropyl-1-methylbenzene
2-Hydroxycymene
2-Methyl-5-(1-methylethyl)-phenol
3-Isopropyl-6-methyl-phenol
5-Isopropyl-2-methyl-phenol
6-Methyl-3-isopropylphenol
Antioxine
BENZENE,2-hydroxy,4-isopropyl,1-methyl carvacrol
Carvacrol
Cymenol
Cymophenol
FEMA 2245
Hydroxy-P-cymene
Isopropyl-O-cresol
Isothymol
Isothymol (=2-isopropyl-4-methyl phenol)
Karvakrol
Methyl-5-(1-methylethyl)phenol
O-Thymol
Oxycymol
P-Cymen-2-ol
P-Cymene-2-ol
P-Mentha-1,3,5-trien-2-ol
5-Isopropyl-2-methylphenol

CAS number

89-83-8

Weight

Average: 150.2176
Monoisotopic: 150.10446507

InChI Key

RECUKUPTGUEGMW-UHFFFAOYSA-N

InChI

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

IUPAC Name

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

Traditional IUPAC Name

carvacrol

Chemical Formula

C₁₀H₁₄O

SMILES

CC(C)C1=CC=C(C)C(O)=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
O-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:3440 )
p-menthane monoterpenoid (CHEBI:3440 )
botanical anti-fungal agent (CHEBI:3440 )
Menthane monoterpenoids (C09840 )
Cyclic monoterpenes (C09840 )
Menthane monoterpenoids (LMPR0102090017 )

Physical Properties

State

Solid

Charge

Melting point

51.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.9 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	3.30 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	3.2	ALOGPS
logP	3.43	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.42	ChemAxon
pKa (Strongest Basic)	-5.5	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	17.88 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	FDB014512
Spice	FDB014512
Thymol	FDB014512
Woody	FDB014512

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-1900000000-ef32f1d484b3c21ba134	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0900000000-b0006c01682dd3cd5032	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-6900000000-b77d2bc899f0364b95e6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-1900000000-ef32f1d484b3c21ba134	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0900000000-b0006c01682dd3cd5032	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-6900000000-b77d2bc899f0364b95e6	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k9i-3900000000-3be7e2bf4cdcc1a3e998	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9770000000-bfcdd12ac3af31af5d4d	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-0udi-0900000000-712524634787b6273922	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0a4i-0900000000-68880fe4b40d01db1716	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-8a9c632983ea0192ea86	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2900000000-4025c9fcbf16ad5dc869	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lec-9500000000-d3d61486758aa2c087bd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-15cb932418fd2314ac11	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-d2de9111b421bbc52608	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ls-3900000000-cae7a0406163986d258d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-22917433edc8ad9dbc2e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-ec9ac6baa6857dfd0b60	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05o3-7900000000-102f2168cf41515b9d4d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k96-6900000000-a06e5e505d76cfe47ff1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9400000000-97275967d77e94a70074	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9100000000-623acc544c8c7c8ef29a	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-000i-3900000000-33df3527bcfd42c1888b	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	27607
HMDB ID	HMDB01878
Pubchem Compound ID	6989
Kegg ID	C09908
ChemSpider ID	21105867
FOODB ID	FDB014512
Wikipedia ID	Carvacrol
BioCyc ID	Not Available

Structure for #<Compound:0xae9b3080>