Basic information Chemical properties Application Preparative methods Toxicity Safety Related Supplier
- Product Name:Guaiacol
- Synonyms: PYROCATECHOL MONOMETHYL ETHER PYROGUAIAC ACID O-METHOXYPHENOL O-METHYLCATECHOL O-HYDROXYANISOLE CATECHOL MONOMETHYL ETHER Gulaiacol GUAJACOL
- Product Categories: Aromatic Ethers Aromatics Compounds Pharmaceutical Intermediates Antioxidant Biochemistry Aromatics - ANASTIL
- Mol File:90-05-1.mol
Guaiacol Chemical Properties
- Melting point:26-29 °C(lit.)
- Boiling point:205 °C(lit.)
- Density 1.129 g/mL at 25 °C(lit.)
- vapor density 4.27 (vs air)
- vapor pressure 0.11 mm Hg ( 25 °C)
- refractive index n
- FEMA 2532 | GUAIACOL
- Flash point:180 °F
- storage temp. Refrigerator
- solubility H2O: insoluble
- form Liquid After Melting
- pka9.98(at 25℃)
- color Clear colorless to light yellow
- PH5.4 (10g/l, H2O, 20℃)
- Water Solubility 17 g/L (15 ºC)
- FreezingPoint 28℃
- Sensitive Air Sensitive
- Merck 14,4553
- JECFA Number713
- BRN 508112
- Stability:Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents.
- CAS DataBase Reference90-05-1(CAS DataBase Reference)
- NIST Chemistry ReferencePhenol, 2-methoxy-(90-05-1)
- EPA Substance Registry SystemPhenol, 2-methoxy-(90-05-1)
- Hazard Codes Xn,T,Xi
- Risk Statements 22-36/38
- Safety Statements 26
- RIDADR 2810
- WGK Germany 1
- RTECS SL7525000
- Autoignition Temperature750 °C
- Hazard Note Toxic/Irritant
- TSCA Yes
- HazardClass 6.1(b)
- PackingGroup II
- HS Code 29095010
- Hazardous Substances Data90-05-1(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 725 mg/kg (Taylor)
Guaiacol Usage And Synthesis
- Chemical propertiesIt 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.
- ApplicationUsed 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
- Preparative methodsIt 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.
- ToxicityLD50:900 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.
- DescriptionGuaiacol has a characteristic sweet odor. It is slightly phenolic. Guaiacol is obtained from hardwood tar or synthetically from onitrophenol via o-anisidine.
- Chemical PropertiesGuaiacol has a characteristic sweet odor. It is slightly phenolic.
- Chemical PropertiesLight Yellow Oil
- OccurrenceDetected 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
- UsesGuaiacol 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.
- UsesSynthetic flavors, medicine (expectorant).
- UsesA phenolic natural product and reducing co-substrate for COX reactions.
- DefinitionChEBI: A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.
- Aroma threshold valuesDetection: 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 valuesTaste characteristics at 2.0 ppm: woody, phenolic, bacon, savory, smoky and medicinal.
- General DescriptionColorless 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.
- Air & Water ReactionsSensitive to air and light (darkens). Slightly water soluble.
- Reactivity ProfileGuaiacol may react with oxidizing materials. Guaiacol forms salts readily with bases.
- HazardToxic by ingestion and skin absorption.
- Fire HazardGuaiacol is combustible.
- Chemical SynthesisObtained from hardwood tar or synthetically from o-nitrophenol via o-anisidine.
- Purification MethodsCrystallise guaiacol from *benzene/pet ether or distil it in a vacuum. [Beilstein 6 H 768, 6 IV 5563.]
Guaiacol Preparation Products And Raw materials
- Raw materials2-Nitrochlorobenzeneo-AnisidinePine oilCREOSOTEGUM GUAIAC
- Preparation ProductsVanillinPyrocatecholEugenol2,3-Dihydro-2,2-dimethyl-7-benzofuranol 3-Hydroxy-4-methoxybenzaldehyde1,2-DimethoxybenzeneGuaifenesinTriclosan2-METHOXYPHENOXYACETIC ACID5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile3-Methyl-2-(3,4-dimethoxyphenyl)butyronitrile4-Bromo-2-methoxyphenolHomovanillic acid1-ALLYLOXY-2-METHOXY-BENZENE3,4-Dimethoxybenzyl chlorideDL-4-HYDROXY-3-METHOXYMANDELIC ACIDguacetisal Terpinyl cyclohexanol mixtureGuaiacol glycidyl etherSulfogaiacol
- 3,4-Dimethoxyphenol 4-Methoxyphenol 3-(o-Methoxyphenoxy)-1,2-propanediol, Guaiacol Glyceryl Ether, Robitussin,GUAIACOL GLYCERYL ETHER SIGMA REFERENCE STANDARD p-(2-Methoxyethyl) phenol 2-Phenylphenol 2-(Trifluoromethoxy)aniline 2-Aminophenol CHLOROPHOSPHONAZO III 2,6-Dimethoxyphenol METHOXYPHENOL, PARA-(SG) 2-Iodophenol Guaiacol o-Anisic acid 2-Methoxy-5-nitrophenol sodium salt guaiacol sulphdnate potassium,Potassium guaiacol sulphonate o-Anisaldehyde 2-Methoxy-5-nitrophenol 2'-Methoxyacetophenone
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