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Guaiacol

Guaiacol structure

CAS No:
90-05-1
Formula:
C7H8O2
Chemical Name:
Guaiacol
Synonyms:
PYROCATECHOL MONOMETHYL ETHER;PYROGUAIAC ACID;O-METHOXYPHENOL;O-METHYLCATECHOL;O-HYDROXYANISOLE;CATECHOL MONOMETHYL ETHER;Gulaiacol;GUAJACOL
Categories:
Active Pharmaceutical Ingredients > Respiratory Drugs

Description

Guaiacol, a phenolic compound isolated from Guaiac resin, inhibits LPS-stimulated COX-2 expression and NF-κB activation[1]. Anti-inflammatory activity[1].

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.

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.

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.

Crystallise guaiacol from *benzene/pet ether or distil it in a vacuum. [Beilstein 6 H 768, 6 IV 5563.]

Guaiacol Basic Attributes

Molecular Weight：

124.14

Exact Mass：

124.14

BRN：

508112

EC Number：

201-964-7

TSCA：

TSCA listed

Color/Form：

Clear colorless to light yellow

HScode：

29095010

Characteristics

PSA：

29.46000

XLogP3：

1.3

Appearance：

Creosote, beechwood is a colorless to yellowish oily liquid with a smoky odor and caustic burning taste. (NTP, 1992)

Density：

1.129 g/mL at 25 °C (lit.)

Melting Point：

26-29 °C (lit.)

Boiling Point：

205 °C (lit.)

Flash Point：

82ºC

Refractive Index：

n20/D1.543(lit.)

Water Solubility：

17 g/L (15 ºC)

Storage Conditions：

Refrigerator

Vapor Pressure：

0.11 mm Hg ( 25 °C)

Vapor Density：

4.27 (vs air)

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.

Odor：

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

Taste：

CAUSTIC, BURNING TASTE

PH：

5.4 (10g/l, H2O, 20℃)

PKA：

9.98(at 25℃)

Henrys Law Constant：

8.6×100mol/(m3Pa) at 25℃, McFall et al. (2020)

Air and 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.

Autoignition Temperature：

750 °C

Critical Temperature & Pressure：

2-8°C

Safety Information

Packing level：

Hazard category：

6.1(b)

Transport codes：

UN 2810

wgk germany：

hazard class code：

Xn,T,Xi

safety instructions：

RTECS Number：

SL7525000

Marks：

Storage features：

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs.

Stability/Shelf Life：

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

Precautionary statement(s)：

P280-P301 + P312 + P330-P305 + P351 + P338-P337 + P313

Hazard Statements：

Toxic by ingestion and skin absorption.

RIDADR：

2810

Fire Hazards：

Guaiacol is combustible.

Guaiacol Use and Manufacturing

Used in medicine, dye and perfume intermediates. It is used to manufacture calcium guaiacolsulfonate in medicine and vanillin and artificial musk in the perfume industry.

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.

Synthetic flavors, medicine (expectorant).

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

Material

Tetrahydrofuran

Cyclohexane

Pyridine

Catechol

Vanillin

Sodium methoxide

Dimethyl carbonate

Ethanol

Acetic acid

Methanol

Dimethylformamide

1-Butanol

Benzene

Hydrochloric acid

Phosphoric acid

Dimethyl sulfate

Hydrogen peroxide

2-Methoxyaniline

o-Xylene

4-tert-Butylcatechol

Downstream Products

Toluene

Cyclohexanol

Cyclohexanone

Phenol

Fumaric acid

Cyclohexane

Catechol

Vanillin

Oxalic acid

Cyclopentane

Formic acid

Methanol

Benzene

Methacrylic acid

2-Ethoxyphenol

o-Cresol

o-Phenylenediamine

Methylcyclopentane

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