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Guaiacol

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CAS:90-05-1
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Guaiacol Basic information
Product Name:Guaiacol
Synonyms:PYROCATECHOL MONOMETHYL ETHER;PYROGUAIAC ACID;O-METHOXYPHENOL;O-METHYLCATECHOL;O-HYDROXYANISOLE;CATECHOL MONOMETHYL ETHER;Gulaiacol;GUAJACOL
CAS:90-05-1
MF:C7H8O2
MW:124.14
EINECS:201-964-7
Product Categories:ANASTIL;Pharmaceutical Intermediates;Aromatics Compounds;Antioxidant;Biochemistry;Aromatics;Aromatic Ethers;90-05-1;bc0001
Mol File:90-05-1.mol
Guaiacol Structure
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 n20/D 1.543(lit.)
FEMA 2532 | GUAIACOL
Fp 180 °F
storage temp. 2-8°C
solubility H2O: insoluble
pka9.98(at 25℃)
form Liquid After Melting
color Clear colorless to light yellow
PH5.4 (10g/l, H2O, 20℃)
Odorat 1.00 % in dipropylene glycol. phenolic smoke spice vanilla woody
Odor Threshold0.0074ppm
Odor Typephenolic
Water Solubility 17 g/L (15 ºC)
FreezingPoint 28℃
Sensitive Air Sensitive
Merck 14,4553
JECFA Number713
BRN 508112
Dielectric constant11.0(-18℃)
Stability:Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents.
Cosmetics Ingredients FunctionsPERFUMING
InChI1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
InChIKeyLHGVFZTZFXWLCP-UHFFFAOYSA-N
SMILESCOc1ccccc1O
LogP1.34
CAS DataBase Reference90-05-1(CAS DataBase Reference)
NIST Chemistry ReferencePhenol, 2-methoxy-(90-05-1)
EPA Substance Registry SystemGuaiacol (90-05-1)
Safety Information
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 TSCA listed
HazardClass 6.1(b)
PackingGroup II
HS Code 29095010
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Hazardous Substances Data90-05-1(Hazardous Substances Data)
ToxicityLD50 orally in rats: 725 mg/kg (Taylor)
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.
MSDS Information
ProviderLanguage
1-Hydroxy-2-methoxybenzene English
SigmaAldrich English
ACROS English
ALFA English
Guaiacol Usage And Synthesis
Chemical PropertiesGuaiacol 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. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is also present in wood smoke, as a product of pyrolysis of lignin.
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: Guaiacol is a monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position. It has a role as an expectorant, a disinfectant, a plant metabolite and an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor. It is functionally related to a catechol.
PreparationGuaiacol 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 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 DescriptionGuaiacol is a 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. It is an agent thought to have disinfectant properties and used as an expectorant.
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.
Biochem/physiol ActionsGuaiacol, 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.
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.]
Toxicity evaluationLD50:900 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.
Tag:Guaiacol(90-05-1) Related Product Information
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