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Chemical properties
It appears as white or slightly yellow crystals or colorless to pale yellow transparent oily liquid. It has a special aromatic smell. It is slightly soluble in water and benzene. It is easily soluble in glycerol. It is miscible with ethanol, ether, chloroform, oil and glacier acetic acid.
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Application
Used for pharmaceuticals, dyes and spices intermediates
Mainly used for the preparation of coffee, vanilla, fumigation and tobacco flavor.
Used for the synthesis of dyes, also used as analytical reagents
In medicine, it can be used for the manufacture of calcium guaiacol sulfonate; in the spice industry, it is used the manufacture of vanillin and artificial musk; Used for test copper, hydrocyanic acid and nitrite
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Preparative methods
It can be obtained by diazotization and hydrolysis of anthranium anisole.
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.
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Toxicity
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.
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Description
Guaiacol has a characteristic sweet odor. It is slightly phenolic.
Guaiacol is obtained from hardwood tar or synthetically from onitrophenol
via o-anisidine.
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Chemical Properties
Guaiacol has a characteristic sweet odor. It is slightly phenolic.
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Chemical Properties
Light Yellow Oil
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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
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Uses
A phenolic natural product and reducing co-substrate for COX reactions.
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Uses
Synthetic flavors, medicine (expectorant).
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Uses
Guaiacol is a precursor of vanillin and santalidol (a synthetic sandal-
wood fragrance). it is obtained from wood tar by the destructive
distillation of hardwood, by the distillation of the phenol fraction
of coal tar, or through the use of o-dichlorobenzene. it is processed
to yield vanillin.
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Definition
ChEBI: A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.
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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.
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Taste threshold values
Taste characteristics at 2.0 ppm: woody, phenolic, bacon, savory, smoky and medicinal.
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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.
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Air & Water Reactions
Sensitive to air and light (darkens). Slightly water soluble.
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Reactivity Profile
Guaiacol may react with oxidizing materials. Guaiacol forms salts readily with bases.
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Hazard
Toxic by ingestion and skin absorption.
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Fire Hazard
Guaiacol is combustible.
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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.
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Chemical Synthesis
Obtained from hardwood tar or synthetically from o-nitrophenol via o-anisidine.
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Purification Methods
Crystallise guaiacol from *benzene/pet ether or distil it in a vacuum. [Beilstein 6 H 768, 6 IV 5563.]
