5-Isopropyl-2-methylphenol
Carvacrol
Grundinformationen
- CAS
499-75-2- Standard-SMILES
Cc1ccc(C(C)C)cc1O- InChIKey
RECUKUPTGUEGMW-UHFFFAOYSA-N- Summenformel
- C10H14O
- Durchschnittliche Molmasse
- 150,22 g/mol
- Monoisotopische Masse
- 150,10446507
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Carvacrol
- IUPAC
- 2-methyl-5-propan-2-ylphenol
- Lokaler Name
- 5-Isopropyl-2-methylphenol
- Englischer Name
- Carvacrol
- Summenformel
- C10H14O
- Molmasse
- 150.22
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
499-75-2- PubChem CID
- 10364
- DTXSID
DTXSID6042074- ChEMBL
CHEMBL281202- ChEBI
CHEBI:3440- UNII
- 9B1J4V995Q
- EC Number
- 207-889-6
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,1
- Polarare Oberfläche (TPSA)
- 20,2 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 120
Experimentelle und physikochemische Eigenschaften
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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
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)]
Chemie und Industrie
Pharmakologische Informationen
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
Verwendung und Herstellung
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
Zugehörige Reaktionen
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