Cannabis Compound Database: Showing Compound Card for Carvacrol (CDB000092)

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Record Information

Version

1.0

Created at

2020-03-18 23:24:28 UTC

Updated at

2020-12-07 19:07:05 UTC

CannabisDB ID

CDB000092

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Carvacrol

Description

Carvacrol or 5-isopropyl-2-methylphenol is a naturally occurring organic compound classified as an alkylphenol (containing at least one aromatic ring) although biochemically, it is a monoterpenoid synthesized from isoprene units. Carvacrol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Carvacrol has a camphor, spice, and thymol taste with a characteristic pungent, warm odor of oregano. Carvacrol is also found in cannabis plants (PMID: 6991645 ), Carvacrol is found in highest concentrations in pot marjorams, common thymes, and black walnuts and in lower concentrations in rosemaries, common oregano, and sweet marjorams. Carvacrol was detected in pepper (spice), tamarinds, peppermints, lovages, and sweet basils making carvacrol a potential biomarker for the consumption of these foods. It has been added as a flavoring agent, preservative and fragrance in products. Its bioactivity and toxicological properties have been reviewed (PMID: 24915411 ). As a constituent of many essential oils, carvocrol was demonstrated to have anti-biofilm and anti-microbial properties (PMID: 30067078 ) and acts as an anti-viral against the norovirus (PMID: 24779581 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hydroxy-2-methyl-5-isopropylbenzene	ChEBI
1-Methyl-2-hydroxy-4-isopropylbenzene	ChEBI
2-Hydroxy-p-cymene	ChEBI
2-Methyl-5-(1-methylethyl)phenol	ChEBI
2-Methyl-5-isopropylphenol	ChEBI
2-p-Cymenol	ChEBI
3-Isopropyl-6-methylphenol	ChEBI
5-Isopropyl-O-cresol	ChEBI
2-Hydroxy-4-isopropyl-1-methylbenzene	HMDB
2-Hydroxycymene	HMDB
2-Methyl-5-(1-methylethyl)-phenol	HMDB
3-Isopropyl-6-methyl-phenol	HMDB
5-Isopropyl-2-methyl-phenol	HMDB
6-Methyl-3-isopropylphenol	HMDB
Antioxine	HMDB
BENZENE,2-hydroxy,4-isopropyl,1-methyl carvacrol	HMDB
Carvacrol	HMDB
Cymenol	HMDB
Cymophenol	HMDB
FEMA 2245	HMDB
Hydroxy-P-cymene	HMDB
Isopropyl-O-cresol	HMDB
Isothymol	HMDB
Isothymol (=2-isopropyl-4-methyl phenol)	HMDB
Karvakrol	HMDB
Methyl-5-(1-methylethyl)phenol	HMDB
O-Thymol	HMDB
Oxycymol	HMDB
P-Cymen-2-ol	HMDB
P-Cymene-2-ol	HMDB
P-Mentha-1,3,5-trien-2-ol	HMDB
5-Isopropyl-2-methylphenol	ChEBI

Chemical Formula

C₁₀H₁₄O

Average Molecular Weight

150.22

Monoisotopic Molecular Weight

150.1045

IUPAC Name

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

Traditional Name

carvacrol

CAS Registry Number

499-75-2

SMILES

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

InChI Identifier

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

InChI Key

RECUKUPTGUEGMW-UHFFFAOYSA-N

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Poaceae

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Household products:

Antimicrobial agent

Food and nutrition:

Flavoring agent

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	3.5 °C	Not Available
Boiling Point	237.7 °C	Wikipedia
Water Solubility	1.25 mg/mL at 25 °C	Not Available
logP	3.49	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-000i-3900000000-33df3527bcfd42c1888b	2015-03-01	View Spectrum
GC-MS	Carvacrol, non-derivatized, GC-MS Spectrum	splash10-000i-1900000000-ef32f1d484b3c21ba134	Spectrum
GC-MS	Carvacrol, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-b0006c01682dd3cd5032	Spectrum
GC-MS	Carvacrol, non-derivatized, GC-MS Spectrum	splash10-000i-6900000000-b77d2bc899f0364b95e6	Spectrum
GC-MS	Carvacrol, non-derivatized, GC-MS Spectrum	splash10-000i-1900000000-ef32f1d484b3c21ba134	Spectrum
GC-MS	Carvacrol, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-b0006c01682dd3cd5032	Spectrum
GC-MS	Carvacrol, non-derivatized, GC-MS Spectrum	splash10-000i-6900000000-b77d2bc899f0364b95e6	Spectrum
Predicted GC-MS	Carvacrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0k9i-3900000000-3be7e2bf4cdcc1a3e998	Spectrum
Predicted GC-MS	Carvacrol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9770000000-bfcdd12ac3af31af5d4d	Spectrum
Predicted GC-MS	Carvacrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-0udi-0900000000-712524634787b6273922	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0a4i-0900000000-68880fe4b40d01db1716	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-8a9c632983ea0192ea86	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2900000000-4025c9fcbf16ad5dc869	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lec-9500000000-d3d61486758aa2c087bd	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-15cb932418fd2314ac11	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-d2de9111b421bbc52608	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ls-3900000000-cae7a0406163986d258d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-22917433edc8ad9dbc2e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-ec9ac6baa6857dfd0b60	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05o3-7900000000-102f2168cf41515b9d4d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k96-6900000000-a06e5e505d76cfe47ff1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9400000000-97275967d77e94a70074	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9100000000-623acc544c8c7c8ef29a	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0035770

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carvacrol

METLIN ID

Not Available

PubChem Compound

10364

PDB ID

Not Available

ChEBI ID

3440

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Suntres ZE, Coccimiglio J, Alipour M: The bioactivity and toxicological actions of carvacrol. Crit Rev Food Sci Nutr. 2015;55(3):304-18. doi: 10.1080/10408398.2011.653458. [PubMed:24915411 ]
Marchese A, Arciola CR, Coppo E, Barbieri R, Barreca D, Chebaibi S, Sobarzo-Sanchez E, Nabavi SF, Nabavi SM, Daglia M: The natural plant compound carvacrol as an antimicrobial and anti-biofilm agent: mechanisms, synergies and bio-inspired anti-infective materials. Biofouling. 2018 Jul;34(6):630-656. doi: 10.1080/08927014.2018.1480756. Epub 2018 Aug 1. [PubMed:30067078 ]
Gilling DH, Kitajima M, Torrey JR, Bright KR: Antiviral efficacy and mechanisms of action of oregano essential oil and its primary component carvacrol against murine norovirus. J Appl Microbiol. 2014 May;116(5):1149-63. doi: 10.1111/jam.12453. Epub 2014 Feb 12. [PubMed:24779581 ]

Showing Compound Card for Carvacrol (CDB000092)

Structure for CDB000092 (Carvacrol)