Carvacrol
Basic information
- CAS
499-75-2- Standard SMILES
Cc1ccc(C(C)C)cc1O- InChIKey
RECUKUPTGUEGMW-UHFFFAOYSA-N- Molecular formula
- C10H14O
- Average molar mass
- 150.22 g/mol
- Monoisotopic mass
- 150.10446507
Overview
Carvacrol is a phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1). It has a role as a TRPA1 channel agonist, a volatile oil component, an antimicrobial agent, an agrochemical and a flavouring agent. It is a p-menthane monoterpenoid, a member of phenols and a botanical anti-fungal agent. It derives from a hydride of a p-cymene.
Names & identifiers
- Preferred name
- Carvacrol
- IUPAC
- 2-methyl-5-propan-2-ylphenol
- English name
- Carvacrol
- Molecular formula
- C10H14O
- Molecular weight
- 150.22
Names & synonyms
CARVACROL5-Isopropyl-2-methylphenol499-75-2Isopropyl-o-cresolAntioxine2-p-Cymenol5-Isopropyl-o-cresol2-Hydroxy-p-cymenePhenol, 2-methyl-5-(1-methylethyl)-Karvakrolp-Cymen-2-ol2-Methyl-5-isopropylphenol
Show more names
o-ThymolISOTHYMOLCymenolFEMA 22452-hydroxy-p-cymen
2-methyl-5-propan-2-ylphenol3-Isopropyl-6-methylphenolp-Cymene, 2-hydroxy-1-Hydroxy-2-methyl-5-isopropylbenzeneFEMA No. 2245Phenol, 5-isopropyl-2-methyl-1-Methyl-2-hydroxy-4-isopropylbenzeneDENTOL
Database identifiers
- CAS
499-75-2- PubChem CID
- 10364
- DTXSID
DTXSID6042074- ChEMBL
CHEMBL281202- ChEBI
CHEBI:3440- UNII
- 9B1J4V995Q
- EC Number
- 207-889-6
- Nikkaji
- J6.180H
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 120
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Oils and Extracts
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
CosmeticsCosmetic ingredients (Carvacrol) -> CIR (Cosmetic Ingredient Review)
SpringerMaterials PropertiesDensity
Fragrances
Fragrance Ingredient (Carvacrol) -> IFRA transparency List
Fragrance
Pesticides
Other Treatment
Active substance -> EU Pesticides database: Pending
LogP
3.49
3.49
Odor
THYMOL ODOR
MEDICINAL SMOKE ODOR
TasteEXCELLENT SMOKE TASTE, @ 1-5 PPM
Food Additives
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.1% (2 of 1828) of reports.
Warning
H302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1828 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Phenol, 2-methyl-5-(1-methylethyl)-
Regulation (EC) No 1831/2003 (amended)
Phenol, 2-methyl-5-(1-methylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2-methyl-5-(1-methylethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Carvacrol (EC: 207-889-6)
5-Isopropyl-2-methylphenol: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryEmergency treatment: Irritants; [HSDB] Causes severe irritation on rabbit skin; Causes somnolence and convulsions at lethal doses; [RTECS] Safe when used as a flavoring agent in food; [JECFA]
FDA Requirements
172.515
121.1164; LIMITATIONS: SYNTHETIC FLAVOR.
Special Reports
REVIEW WITH 42 REF ON CARVACROL INCL TOXICITY, IRRITATION, SENSITIZATION, METAB, PERCUTANEOUS ABSORPTION, PHARMACOLOGY, CYTOTOXICITY, CHEMOTHERAPY, & EFFECT ON ISOLATED TISSUES & ORGANELLES.[OPDYKE DL J; MONOGRAPH ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17(ISS SUPPL) 743 (1979)]
Chemistry & industry
Pharmacology
Metabolism/Metabolites
/WHEN FED TO RABBITS,/ THE SUBSTITUTED MONOPHENOLS, THYMOL & CARVACROL, WHICH OCCUR IN ESSENTIAL OILS OF PLANTS...ARE...CONJUGATED WITH GLUCURONIC ACID & SULFATE.
CARVACROL IS METABOLIZED BY CONJUGATION WITH GLUCURONIC ACID & SULFATE.
Carvacrol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(2-methyl-5-propan-2-ylphenoxy)oxane-2-carboxylic acid and (2-methyl-5-propan-2-ylphenyl) hydrogen sulfate.
Absorption, Distribution and Excretion
CARVACROL APPEARS TO BE SLOWLY ABSORBED FROM INTESTINE IN RABBIT, SINCE 22 HR AFTER ADMIN OF 1.5 G, SOME 30% WAS STILL IN GASTRO-INTESTINAL TRACT, ABOUT 25% OF DOSE HAVING BEEN EXCRETED IN URINE.
CARVACROL APPLIED TO INTACT SHAVED ABDOMINAL SKIN OF MOUSE WAS NOT ABSORBED WITHIN 2 HR.
Cellular LocationsExtracellular
Uses & manufacturing
Uses
CIR ingredient: Carvacrol
Found in oil of origanum, thyme, marjoram, and summer savory; Used as a disinfectant, fungicide, and anthelmintic (nematodes); Also used in organic syntheses and in perfumes and flavorings; [Hawley] Origanum oil is about 60% carvacrol; [HSDB]
Using Disinfectants or Biocides [Category: Clean]
DISINFECTANT; IN ORGANIC SYNTHESES
MEDICATION: ANTIFUNGAL; ANTHELMINTIC AGENT
PERFUMES; FLAVORING
U.S. Production2023: 2,500 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing
FROM P-CYMENE BY SULFONATION & SUBSEQUENT ALKALI FUSION. HIXSON & MCKEE, CHEM ZENTR, II: 851, 1919; GIBBS & PHILLIPS, J IND ENG CHEM, 12: 145, 1920.
Related reactions
13 records
Compound notes
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