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Carvacrol

Carvacrol structure

CAS No:
499-75-2
Formula:
C10H14O
Chemical Name:
Carvacrol
Synonyms:
Phenol,2-methyl-5-(1-methylethyl)-;Carvacrol;2-Methyl-5-(1-methylethyl)phenol;Antioxine;p-Cymen-2-ol;2-Hydroxy-p-cymene;2-Methyl-5-isopropylphenol;5-Isopropyl-2-methylphenol;5-Isopropyl-o-cresol;6-Methyl-3-isopropylphenol;2-Hydroxy-1-methyl-4-(1-methylethyl)benzene;3-Isopropyl-6-methylphenol;Isopropyl o-cresol;Isothymol;NSC 6188;Dentol;2-Methyl-5-(propan-2-yl)phenol
Categories:
Cosmetic Ingredient > Perfuming

Description

Carvacrol is a monoterpenoid phenol isolated from Lamiaceae family plants, with antioxidant, anti-inflammatory and anticancer properties. Carvacrol causes cell cycle arrest in G0/G1, downregulates Notch-1, and Jagged-1, and induces apoptosis[1].

Liquid|Colourless to pale yellow liquid, pungent, spicy odour

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 volatile oil component, a flavouring agent, an antimicrobial agent, an agrochemical and a TRPA1 channel agonist. It is a member of phenols, a p-menthane monoterpenoid and a botanical anti-fungal agent. It derives from a hydride of a p-cymene.

Carvacrol Basic Attributes

Molecular Weight：

150.21800

Exact Mass：

150.22

EC Number：

207-889-6

UNII：

9B1J4V995Q

NSC Number：

6188

DSSTox ID：

DTXSID6042074

Color/Form：

NEEDLES|COLORLESS OR YELLOWISH, THICK LIQUID

HScode：

2907199090

Characteristics

PSA：

20.23000

XLogP3：

3.1

Appearance：

Liquid

Density：

0.976 g/cm³ @ Temp: 20 °C

Melting Point：

1 °C

Boiling Point：

237-238 °C @ Press: 760 Torr

Flash Point：

85ºC

Refractive Index：

n20/D 1.522(lit.)

Water Solubility：

H2O: Insoluble

Toxicity：

LD orally in rabbits: 100 mg/kg (Kochmann)

Odor：

THYMOL ODOR

Taste：

EXCELLENT SMOKE TASTE, @ 1-5 PPM

Experimental Properties：

SOLIDIFICATION ABOUT 0 °C|UV: 6-304 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /o-Cresol, 6-isopropyl/

Safety Information

Packing level：

III

Hazard category：

Transport codes：

UN 3265

wgk germany：

hazard class code：

R22; R34

safety instructions：

S26-S36/37/39-S45

RTECS Number：

FI1225000

Marks：

Stability/Shelf Life：

Stable. Combustible. Incompatible with strong bases, strong oxidizing agents.

Precautionary statement(s)：

P280-P305 + P351 + P338-P310

Hazard Statements：

H302-H314

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)]

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 1719 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

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.

Drug Information

Reported Fatal Dose：

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).

Absorption：

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.

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 (2-methyl-5-propan-2-ylphenyl) hydrogen sulfate and (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(2-methyl-5-propan-2-ylphenoxy)oxane-2-carboxylic acid.

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.

MeSH Entry Terms：

5-isopropyl-2-methylphenol

Carvacrol Use and Manufacturing

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.|...BY CHLORINATION OF ALPHA-PINENE WITH TERT-BUTYL HYPOCHLORITE: RITTER, GINSBURG, J AM CHEM SOC 72, 2381 (1950); FROM 2-BROMO-P-CYMOL: STRUBELL, BAUMGARTEL, ARCH PHARM 291, 66 (1958).

Uses

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

Formulations：

THE COMMERCIAL PRODUCT CONSISTS OF A MIXTURE OF ISOMERS DIFFERING BECAUSE OF THE POSITION OF THE ISOPROPYL RADICAL. THE TECHNICAL & PURE QUALITY ARE DIFFERENT BECAUSE OF THE ODOR CHARACTERISTICS.|THE MAIN CONSTITUENT/OF ORIGANUM OIL/IS CARVACROL (ca 60%)

Manufacturing Info：

Phenol, 2-methyl-5-(1-methylethyl)-: ACTIVE|FLAVORS USEFUL IN: SMOKE FLAVORS, SPICE, MEAT FLAVORS.|REPORTED USES: /IN/ NON-ALCOHOLIC BEVERAGES 26 PPM; ICE CREAM, ICES, ETC 34 PPM; CANDY 92 PPM; BAKED GOODS 120 PPM; CONDIMENTS 37 PPM.|FEMA NUMBER 2245

Analytic Methods：

BY USE OF (13)C NMR, GAS-CHROMATOGRAPHY, & GAS CHROMATOGRAPHY-MASS SPECTROMETRIC ANALYSIS, ESSENTIAL OIL COMPONENTS WERE IDENTIFIED.|THYMOL & CARVACROL CONTENTS WERE DETERMINED WITH HIGH-PERFORMANCE LIQ CHROMATOGRAPHY.

Use Classification：

Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]

Food Additive Classes：

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:150.22
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:150.104465066
Monoisotopic Mass:150.104465066
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Benzonitrile

Phosphorus oxychloride

1,2-Dichloroethane

Oxalic acid

Methanol

Acetonitrile

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