General Description
Colorless to amber crystals or liquid. Density (of solid) 1.129 g/cm3. Solidifies at 28°C (82.4°F), but may remain liquid for a long time even at a much lower temperature. Slightly water soluble . Soluble in aqueous sodium hydroxide. Used medicinally as an expectorant. Used, because of its anti-oxidant properties, as an anti-skinning agent for paints.
Reactivity Profile
O-METHOXYPHENOL(90-05-1) may react with oxidizing materials. O-METHOXYPHENOL(90-05-1) forms salts readily with bases.
Air & Water Reactions
Sensitive to air and light (darkens). Slightly water soluble.
Hazard
Toxic by ingestion and skin absorption.
Fire Hazard
This chemical is combustible.
Description
Guaiacol has a characteristic sweet odor. It is slightly phenolic.
Guaiacol is obtained from hardwood tar or synthetically from onitrophenol
via o-anisidine.
Chemical Properties
Guaiacol, a phenolic product, obtained from hardwood tar or synthetically from onitrophenol via o-anisidine, appears as white or slightly yellow crystals or colorless to light yellow transparent oily liquid. It has a distinctive scent. It is slightly soluble in water and benzene,
also easily soluble in glycerol. And it is miscible with ethanol,
ether, chloroform, oil and glacier acetic acid.
Occurrence
Detected in the distillation product from guaiac resin; guaiacol is found in castoreum oil, in the essential oil from fowers of Pandanus odoratissimus L , in the distillation waters of orange leaves, in the essential oil of Ruta Montana L and in the essential oil of tobacco leaves Also reported found in lemon peel oil, bog blueberry, asparagus, cabbage, celery, onion, chive, tomato, peppermint oil, rye bread, Parmesan cheese, butter, smoked fsh, meats, barley, dried bonito, malt, hardwood smoke, cognac, beer, brandy, rum, whiskies, sherry, grape wines, cocoa, coffee, tea, peanuts, popcorn, soybeans, avocado, beans, mushroom, sesame seed, mango, tamarind, rice dill, licorice, corn oil, cuttlefsh and other sources
Definition
ChEBI: A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.
Preparation
Guaiacol can be obtained by diazotization and hydrolysis of anthranium anisole or obtained from fractionated of wood oil.
In the nature of guaiacol is presented in the guaiacum or pine oil. In the creosote oil obtained from wood dry distillation, guaiacol is the major ingredient. This product could be obtained through fractional distillation of creosote oil. Japan Osaka Refining Company takes o-nitrochlorobenzene as raw material, first synthesizes o-nitroanisole, and then reduces it to o-anisidine, and finally obtains the goods. China's production method is roughly the same. Ingredient consumption quota: 1250 kg / t of amino-containing anisole, 1500 kg / t of sulfuric acid (93%), 700 kg / t of sodium nitrite and 400 kg / t of copper sulfate.
Aroma threshold values
Detection: 3 to 31 ppb; aroma characteristics at 1.0%: phenolic, smoky, spicy, medicinal, vanilla, savory meaty, woody with a bourbon whiskey casky nuance.
Taste threshold values
Taste characteristics at 2.0 ppm: woody, phenolic, bacon, savory, smoky and medicinal.
Biochem/physiol Actions
Guaiacol, along with 2,4,6-trichloroanisole, is responsible for cork taint in wine. A method has been developed for extraction and quantitation of the two compounds.
Synthesis
Obtained from hardwood tar or synthetically from o-nitrophenol via o-anisidine.
Purification Methods
Crystallise guaiacol from *benzene/pet ether or distil it in a vacuum. [Beilstein 6 H 768, 6 IV 5563.]
Toxicity evaluation
LD50:900 mg / kg (rat, subcutaneous).
LD50: 3.7 mg / kg (rabbit, intravenously).
Oral administration of large amount can stimulate the esophagus and stomach, resulting in heart failure, collapse and death.