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

Flash point:

180 °F

storage temp. 

2-8°C

solubility 

H2O: insoluble

form 

Liquid After Melting

pka

9.98(at 25℃)

color 

Clear colorless to light yellow

PH

5.4 (10g/l, H2O, 20℃)

Odor

at 1.00 % in dipropylene glycol. phenolic smoke spice vanilla woody

Odor Type

phenolic

Odor Threshold

0.0074ppm

Water Solubility 

17 g/L (15 ºC)

FreezingPoint 

28℃

Sensitive 

Air Sensitive

JECFA Number

713

Merck 

14,4553

BRN 

508112

Dielectric constant

11.0（-18℃）

Stability:

Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents.

InChIKey

LHGVFZTZFXWLCP-UHFFFAOYSA-N

LogP

1.34

CAS DataBase Reference

90-05-1(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 2-methoxy-(90-05-1)

EPA Substance Registry System

Guaiacol (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 Temperature

750 °C

Hazard Note 

Toxic/Irritant

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

II

HS Code 

29095010

Hazardous Substances Data

90-05-1(Hazardous Substances Data)

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.

Toxicity

LD50 orally in rats: 725 mg/kg (Taylor)

MSDS

• Language:English Provider:1-Hydroxy-2-methoxybenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Guaiacol Usage And Synthesis

Chemical Properties

Guaiacol 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.

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

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.

Uses

Synthetic flavors, medicine (expectorant).

Uses

A phenolic natural product and reducing co-substrate for COX reactions.

Definition

ChEBI: 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.

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.

General Description

Guaiacol 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 Reactions

Sensitive to air and light (darkens). Slightly water soluble.

Reactivity Profile

Guaiacol may react with oxidizing materials. Guaiacol forms salts readily with bases.

Hazard

Toxic by ingestion and skin absorption.

Fire Hazard

Guaiacol is combustible.

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.

Guaiacol(90-05-1)Related Product Information

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