Carvacrol

Carvacrol
Names

Preferred IUPAC name 2-Methyl-5-(propan-2-yl)phenol
Other names 5-Isopropyl-2-methylphenol 2-Methyl-5-(1-methylethyl)phenol
Identifiers
CAS Number	499-75-2^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL281202^Y
ChemSpider	21105867^Y
ECHA InfoCard	100.007.173
IUPHAR/BPS	2497
KEGG	C09840^Y
PubChem	10364
UNII	9B1J4V995Q^Y
InChI InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3^Y Key: RECUKUPTGUEGMW-UHFFFAOYSA-N^Y InChI=1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 Key: RECUKUPTGUEGMW-UHFFFAOYAI
SMILES Cc1ccc(cc1O)C(C)C
Properties
Chemical formula	C10H14O
Molar mass	150.217 g/mol
Density	0.9772 g/cm³ at 20 °C
Melting point	1 °C (34 °F; 274 K)
Boiling point	237.7 °C (459.9 °F; 510.8 K)
Solubility in water	insoluble
Solubility	soluble in ethanol, diethyl ether, carbon tetrachloride, acetone
Magnetic susceptibility (χ)	-109.1·10⁻⁶ cm³/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Carvacrol, or cymophenol, C₆H₃CH₃(OH)(C₃H₇), is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano.

Carvacrol is present in the essential oil of Origanum vulgare (oregano), oil of thyme, oil obtained from pepperwort, and wild bergamot. The essential oil of Thyme subspecies contains between 5% and 75% of carvacrol, while Satureja (savory) subspecies have a content between 1% and 45%. Origanum majorana (marjoram) and Dittany of Crete are rich in carvacrol, 50% and 60-80% respectively.

It is also found in tequila.

Carvacrol inhibits the growth of several bacteria strains, e.g. Escherichia coli and Bacillus cereus. Its low toxicity together with its pleasant taste and smell suggests its use as a food additive to prevent bacterial contamination. In Pseudomonas aeruginosa it causes damages to the cell membrane of these bacteria and, unlike other terpenes, inhibits their proliferation. The cause of the antimicrobial properties is believed to be disruption of the bacteria membrane.
It is a potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1). Application of carvacrol on the human tongue, as well as activation of TRPV3, causes a sensation of warmth. In addition, carvacrol also activates, but then rapidly desensitizes, the pain receptor TRPA1; this explains its pungency.

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Wikipedia