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Carvacrol

2-Methyl-5-(1-methylethyl)phenol

Antioxine · p-Cymen-2-ol · 2-Hydroxy-p-cymene · Isothymol

Monoterpenoid phenol · C₁₀H₁₄O

Chemical structure of Carvacrol
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
499-75-2
Molecular formula
C₁₀H₁₄O
Molecular weight
150.22 g/mol
Aroma
Defining oregano note, pungent, warm, with Mediterranean spice character.

Safety

Phenolic · Mucous membrane irritant

Carvacrol is a monoterpenoid phenol, a weak acid that can be corrosive to tissues. The compound is the major constituent of oregano and savory; it has strong antibacterial activity but also irritates mucous membranes.

Skin. Undiluted on rabbit skin it was severely irritating. A 4 percent patch test on volunteers caused neither irritation nor sensitization; at 0.1 and 1 percent it irritated dermatitis patients. Thyme oil sensitive patients also reacted to carvacrol. In 179 cosmetic-suspect patients, 2 (1.1 percent) reacted to 5 percent.

Oral. Acute oral LD50 in rats is 810 mg/kg. Rabbit oral lethal dose is 100 mg/kg. Rabbit dermal LD50 exceeds 5 g/kg. Dog intravenous lethal dose is 310 mg/kg.

Cardiovascular. Strong antiplatelet aggregation activity in vitro. Satureja khuzestanica oil (93.9 percent carvacrol) reduced blood glucose in diabetic rats.

Reproductive. Pregnant rats given 100–1,000 ppm Satureja khuzestanica on days 0–15 showed no maternal toxicity or teratogenicity; implantation numbers and live fetuses even increased.

Liver. Carvacrol protects rat liver from CCl4 and ischemia-reperfusion damage, with strong antioxidant activity.

Mutagenicity. Non-mutagenic and even antimutagenic in the Ames test. Protected human lymphocytes from hydrogen peroxide DNA damage at low concentrations. At high concentrations of 0.1–2 mM, the compound becomes genotoxic.

Weak genotoxic potential, but DNA-level activity cannot be excluded.


Usage guidelines

Maximum dermal level
Not exceeding 1 percent as constituent, or per IFRA for source oils
Mucous membranes
Avoid direct contact
Pregnancy
Caution for oral use
Anticoagulants, surgery
Caution due to antiplatelet activity
Oils with high content
Oregano 61.6–83.4 percent · Wild marjoram carvacrol CT 76.4–81.0 percent · Winter savory 46.5–75.0 percent

Found in essential oils

Principal sources
Oregano61.6 – 83.4 %
Marjoram wild (carvacrol CT)76.4 – 81.0 %
Savory (summer + winter)43.6 – 75.0 %
Thyme (spike)70.0 %
Thyme (thymol CT, carvacrol CT, thymol/carvacrol CT)5.5 – 43.9 %
Oregano (Mexican)0.5 – 24.8 %
Marjoram wild (linalool CT)23.3 %
Thyme (limonene CT)20.5 %
Thyme (borneol CT)20.0 %
Ajowan1.0 – 16.4 %
Thyme (lemon)15.4 %
Black seed0.5 – 4.2 %
Verbena (white)0 – 1.8 %
Eucalyptus (polybractea cryptone CT)1.1 %
Thyme (linalool CT)1.0 – 1.1 %

Pharmacokinetics

Carvacrol is rapidly excreted in urine, primarily as a tertiary alcohol derivative formed by oxidation of the isopropyl group.


Notes

Carvacrol is the isomer of thymol. Both compounds have strong antimicrobial activity and are used in soaps and skin care for oily and acne-prone skin. Antioxidant activity is significant.

Oral oregano oil is being investigated for antimicrobial activity.