Тимол

Химические свойства

Thymol occurs as colorless or often large translucent crystals, or as a white crystalline powder with a herbal odor (aromatic and thymelike) and a pungent caustic taste.

Вхождение

Reported in the essential oils of Monarda punctata, Satureia thymera, Origanum floribundum, Ocimum viride, Ocimum gratissimum and particularly in thyme (Thymus vulgaris L., T. capitatus, T. serpillum L.), where it is contained up to 50%. Also reported found in citrus peel oils, orange and tangerine juice, bilberry, cranberry, blueberry, papaya, blackberry, celery seed, chive, clove bud, cumin seed, ginger, peppermint oil, corn mint oil, Scotch spearmint oil, nutmeg, parsley, thyme, Gruyere cheese, parmesan cheese, romano cheese, white wine, black tea, plum, sweet and wild marjoram, fenugreek, mango, cardamom, dill herb and seed, licorice, lovage leaf, buckwheat, sweet corn, elder flower, cherimoya, rosemary, lemon balm, Spanish sage, anise hyssop, sweet grass oil, eucalyptus oil and mastic gum oil.

Использование

Thymol is more commonly used in flavor compositions, mainly in toothpaste flavor, cough drops, mouth washes, gargles and chewing gums. It is often used partly for its antiseptic effect in such products. The concentration may vary from 2 to I00 ppm, highest in chewing gums.
A newer use of Thymol is that in imitation Mandarin flavor, since the material was identified in Mandarin peel oil in 1963. It blends excellently with Citrus, Mint, Spice and herbaceous flavor materials or with fruity complexes.

Определение

thymol: A pungent-smelling colourless crystalline compound, C₁₀H₁₄O;m.p. 51°C. It occurs in various essentialoils, particularly oil of thyme,and can be made by using iron(III)chloride to oxidize piperitone (itselfextracted from eucalyptus oil). Itsantiseptic properties are exploited ingargles and mouthwashes.

Методы производства

Thymol is obtained from the volatile oil of thyme (Thymus vulgaris Linne′ (Fam. Labiatae)) by fractional distillation followed by extraction and recrystallization. Thyme oil yields about 20–30% thymol. Thymol may also be produced synthetically from pcymene, menthone, or piperitone, or by the interaction of m-cresol with isopropyl chloride.

Общее описание

Thymol is a monoterpene phenol derivative. It is a key volatile aroma constituent of the essential oil of plants such as thyme, basil, and oregano. It has strong antioxidant, antibacterial, anticarcinogenesis, anti-inflammatory, and antiseptic properties.

Клиническое использование

Isopropyl m-cresol is extracted from oil of Thymus vulgaris(thyme, of the mint family) by partitioning into alkalineaqueous medium followed by acidification. The crystals obtainedfrom the mother liquor are large and colorless, with athymelike odor. Thymol is only slightly soluble in water,but it is extremely soluble in alcohols and other organic solvents.Thymol has mild fungicidal properties and is used inalcohol solutions and in dusting powders for the treatmentof tinea (ringworm) infections.

Профиль безопасности

Poison by ingestion and intravenous routes. Moderately toxic by subcutaneous route. Experimental reproductive effects. Mutation data reported. An allergen. Incompatible with acetanilide. When heated to decomposition it emits acrid smoke and irritating fumes. An FDA over-the-counter drug used as an antibacterial and antifungal agent.

Безопасность

Thymol is used in cosmetics, foods, and pharmaceutical applications as an excipient. However, thymol may be irritating when inhaled or following contact with the skin or eyes. It may also cause abdominal pain and vomiting, and sometimes stimulation followed by depression of the central nervous system following oral consumption; fats and alcohol increase absorption and aggravate symptoms.
Respiratory arrest, attributed to acute nasal congestion and edema, has been reported in a 3-week-old patient due to the erroneous intranasal application of Karvol, a combination product that includes thymol. The patient recovered, but it was recommended that inhalation decongestants should not be used in children under the age of 5 years.
LD50 (guinea pig, oral): 0.88 g/kg
LD50 (mouse, IP): 0.11 g/kg
LD50 (mouse, IV): 0.1 g/kg
LD50 (mouse, oral): 0.64 g/kg
LD50 (mouse, SC): 0.243 g/kg
LD50 (rat, oral): 0.98 g/kg

хранилище

Thymol should be stored in well-closed, light-resistant containers, in a cool, dry, place. Thymol is affected by light.

Несовместимости

Thymol is incompatible with iodine, alkalis, and oxidizing agents. It liquefies, or forms soft masses, on trituration with acetanilide, antipyrine, camphor, monobromated camphor, chloral hydrate, menthol, phenol, or quinine sulfate. The antimicrobial activity of thymol is reduced in the presence of proteins.

Регуляторный статус

GRAS listed. Included in the FDA Inactive Ingredients Database (inhalation, liquid; oral, powder for solution). Included in nonparenteral medicines (topical creams and ointments) licensed in the UK. Included in the Canadian List of Acceptable Nonmedicinal Ingredients.