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Carvacrol
o-Thymol · 5-ISOPROPYL-2-METHYLPHENOL · ISOTHYMOL · Karvakrol · Cymenol · FEMA 2245 · 2-METHYL-5-ISOPROPYLPHENOL · 1-Hydroxy-2-methyl-5-isopropylbenzene
Identifikatoren & physikalische Daten
| CAS No. | 499-75-2 |
|---|---|
| Summenformel | C10H14O |
| Durchschnittliche Molmasse | 150,22 g/mol |
| Monoisotopische Masse | 150,10446507 g/mol |
| SMILES | Cc1ccc(C(C)C)cc1O |
| InChIKey | RECUKUPTGUEGMW-UHFFFAOYSA-N |
| PubChem CID | 10364 |
| ChEMBL | CHEMBL281202 |
| ChEBI | CHEBI:3440 |
| EC No. | 207-889-6 |
| DTXSID | DTXSID6042074 |
| Lokaler Name | 5-Isopropyl-2-methylphenol |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 120 |
| LogP (Verteilungskoeffizient) | 3.49 |
| Geruch | THYMOL ODORMEDICINAL SMOKE ODOR |
| Geschmack | EXCELLENT SMOKE TASTE, @ 1-5 PPM |
| Dichte | 0.976 @ 20 °C/4 °C0.974-0.9790.976 g/mL at 20 °C(lit.) |
| Color/Form | NEEDLESCOLORLESS OR YELLOWISH, THICK LIQUID |
| Löslichkeit | SLIGHTLY SOL IN WATERSOL IN ETHANOL, ETHER, ALKALISVERY SOLUBLE IN ACETONE1.25 mg/mL at 25 °Cinsoluble in watermiscible in oilsmiscible (in ethanol)1.25g/l |
| Flammpunkt | 100 °C224 °F |
| Siedepunkt | 237-238 °C @ 760 MM HG237.70 °C. @ 760.00 mm Hg236-238 °C236-237 °C(lit.) |
| Schmelzpunkt | 1 °C3.5 °C3-4 °C(lit.) |
| Brechungsindex | INDEX OF REFRACTION: 1.5230 @ 20 °C/DMAX ABSORPTION (ALCOHOL): 277.5 NM (LOG E= 3.26)SADTLER REFERENCE NUMBER: 2470 (IR, PRISM)1.521-1.528n20/D 1.522(lit.) |
| Physical Description | Thick colorless liquid[Hawley] Clear, deep yellow liquid[MSDSonline]Colourless to pale yellow liquid, pungent, spicy odour |
| Kovats Retention Index | 12781275128012761289127312971272129812771279130413001294129912911294.31285129513151315.813171311130212932219222521832215221222142222219522092189218622232191 |
| Dampfdruck | 3.09-6.664Pa at 25℃ |
| FEMA | 2245 | CARVACROL |
| Lagerbedingungen | -20°C |
| pKa (Säurekonstante) | 10.38±0.10(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Colorless to Light orange to Yellow |
| Geruch | Penetrating, dry-medicinal (“-phenolic”) - herbaceous odor with a spicy undertone. |
| Geruchsart | spicy |
| Biologische Quelle | synthetic |
| Merck | 14,1872 |
| JECFA Number | 710 |
| BRN | 1860514 |
| Henry-Konstante | 1.5×100 mol/(m3Pa) at 25℃, Martins et al. (2017) |
| Stabilität | Stable. Combustible. Incompatible with strong bases, strong oxidizing agents. |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 |
| InChIKey | RECUKUPTGUEGMW-UHFFFAOYSA-N |
| SMILES | CC(C)c1ccc(C)c(O)c1 |
| LogP (Verteilungskoeffizient) | 3.33-3.49 |
| CAS Datenbank | 499-75-2(CAS DataBase Reference) |
| NIST chemische Informationen | Phenol, 2-methyl-5-(1-methylethyl)-(499-75-2) |
| EPA chemische Informationen | Isopropyl-o-cresol (499-75-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.1% (2 of 1828) of reports.WarningH302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (90.4%): Causes skin irritation [Warning Skin corrosion/irritation]H317 (91.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]H319 (90.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]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.Reported as not meeting GHS hazard criteria per 2 of 1828 reports by companies.There are 12 notifications provided by 1826 of 1828 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | 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)Status: Active Update: 26-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/235625-Isopropyl-2-methylphenol: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Emergency treatment: Irritants[HSDB] Causes severe irritation on rabbit skinCauses somnolence and convulsions at lethal doses[RTECS] Safe when used as a flavoring agent in food[JECFA] |
| FDA-Anforderungen | 172.515121.1164LIMITATIONS: 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 JMONOGRAPH ON FRAGRANCE RAW MATERIALS. CARVACROLFOOD COSMET TOXICOL 17(ISS SUPPL) 743 (1979)] |
| Hazard Classes and Categories | Acute Tox. 4 (99.8%)Skin Irrit. 2 (90.4%)Skin Sens. 1 (91.5%)Eye Irrit. 2 (90.2%) |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Toxizitätsübersicht | The CIR Expert panel concludes Sodium p-Chloro-m-Cresol, p-Chloro-m-Cresol, Chlorothymol, m-Cresol, o-Cresol, Isopropyl Cresols, Thymol, o-Cymen-5-ol, Cavacrol are safe at concentrations up to 0.5% in cosmeticshowever, the available data are insufficient to support the safety of p-Cresol and Mixed Cresols for use in cosmetic products.Safe for use in cosmetics, with qualifications |
| Natural Pollution Sources | FOUND IN OIL OF ORIGANUM, THYME, MARJORAM, SUMMER SAVORY...OCCURS IN BARK OIL OF THUJA ARTICULATA, CAMPHOR OIL, IN OILS OF MONARDA CITRIODORA & MONARDA FISTULOSA, IN SOME SPECIES OF SATUREJA, IN OIL OF VARIOUS SPECIES OF ORIGANUM, THYME, THYMBRA SPICATA L, IN SEED OIL OF PTYCHOTIS AJOWAN DC, & OTHERS. |
| Human Toxicity Excerpts | TECHNICAL GRADE (1.0 & 0.1% IN ETHANOL) PRODUCED POS PATCH TESTS IN PT WITH ACUTE DERMATITIS OF FACE, BUT NO POS RESPONSES IN CONTROL SUBJECTS. TESTED @ 4% IN PETROLATUM, IT PRODUCED NO IRRITATION AFTER 48-HR.CARVACROL SHOWED MODERATE CYTOTOXIC EFFECTS IN HELA CELLS. |
| Non-Human Toxicity Excerpts | SOMEWHAT MORE TOXIC THAN THYMOL IN RATS & RABBITS.EVALUATED FOR MUTAGENIC EFFECTS TO 5 STRAINS OF SALMONELLA TYPHIMURIUM EMPLOYING PROCEDURES DESCRIBED BY AMES, ISOTHYMOL HAD PRONOUNCED MUTAGENICITY.CARVACROL APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN FOR 24 HR UNDER OCCLUSION WAS SEVERELY IRRITATING.WHEN MIXT OF 93% CARVACROL & 7% THYMOL IN ARACHIS OIL WAS ADMIN BY GASTRIC INTUBATION TO CFE STRAIN RATS IN SINGLE DOSE OF 1.5 MMOL/KG, SLIGHT INCR IN PRODUCTION OF LIVER BIPHENYL-4-HYDROXYLASE WAS NOTED.CARVACROL SHOWED PAPAVERINE-LIKE ANTISPASMODIC ACTION ON ISOLATED SMALL INTESTINE OF MOUSE. ADDED TO BOVINE SEMINAL VESICLE MICROSOMES @ 4.1 UG/ML, IT INHIBITED THE IN VITRO FORMATION OF PROSTAGLANDIN E1 BY 50%. |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during LactationOregano (Origanum vulgare) leaves and oil contain carvacrol, thymol, eugenol and rosmarinic acid. Oregano has been used in medicinal doses for respiratory and gastrointestinal disorders and as an antimicrobial. Oregano oil has been advocated as a treatment for lactation-related Candida infection of the nippleshowever, no clinical studies have confirmed the safety or efficacy of this use. Oregano has been used as a galactogogue in Türkiye. No data exist on the safety or efficacy of oregano in nursing mothers or infants. Oregano and oregano oil are "generally recognized as safe" (GRAS) as food ingredients by the U.S. Food and Drug Administration. Oregano is generally well tolerated, but gastrointestinal upset and allergic skin reactions have been reported rarely. Because of a lack of data, oregano in amounts higher than those found in foods as a flavoring should probably be avoided during breastfeeding.Dietary supplements do not require extensive pre-marketing approval from the U.S. Food and Drug Administration. Manufacturers are responsible to ensure the safety, but do not need to prove the safety and effectiveness of dietary supplements before they are marketed. Dietary supplements may contain multiple ingredients, and differences are often found between labeled and actual ingredients or their amounts. A manufacturer may contract with an independent organization to verify the quality of a product or its ingredients, but that does not certify the safety or effectiveness of a product. Because of the above issues, clinical testing results on one product may not be applicable to other products. More detailed information about dietary supplements is available elsewhere on the LactMed Web site.◉ Effects in Breastfed InfantsRelevant published information was not found as of the revision date.◉ Effects on Lactation and Breastmilk |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3265 8/PG 3 |
| Zollcode | 29071990 |
| RTECS-Nr. | FI1225000 |
| R-Sätze (R) | 22-34 |
| Toxizität | LD orally in rabbits: 100 mg/kg (Kochmann) |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 26-36/37/39-45 |
| Gefahrenklasse | 8Acute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Skin Corr. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
| Gefahrstoffdaten | 499-75-2(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Reported found in cumin seed, thyme, oregano, calamus, lovage, myrtle and lemon balm.
Verwenden
Carvacrol is a flavoring agent that is a colorless to pale yellow liquid. it has a spicy and pungent odor, resembling thymol. it is insoluble in water and soluble in alcohol and ether. it is a mixture of the isomeric carvacrols (isopropyl o-creols), and is obtained by chemical synthesis. it is also an ingredient of savory, a fragrant herb in nature.
Herstellung & Synthese
synthetische
From p-cymene by sulfonation and subsequent alkali fusion.