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guaiacol

Product name guaiacol
Synonyms catechol monomethyl ether
2-methoxyphenol
GOST no data
CAS 90-05-1

Guaiacol is a colorless crystalline solid with a characteristic odor. It turns dark upon storage on air and light. It is readily soluble in alcohols, diethyl ether, acetic acid, chloroform, water alkalis. Boundedly soluble in aliphatic hydrocarbons and water (1.7% wt at 17°C). Guaiacol can be distilled with steam.

Guaiacol possess both an ether and phenol chemical properties. It can be methylated by action of dimethyl sulfate resulting in veratrole (dimethyl ether of catechol). It can be also alkylated with allyl alcohol or allyl chloride to form eugenol:

Guaiacol alkylation with allyl alcohol


Guaiacol irritates mucous membrane of eyes and respiratory tract. Being in contact with skin it may cause eczema.

Production.

  • Guaiacol is found in nature. It is a component of guaiacum pitch. It is produced industrially by processing of wood pyrolysis products.
  • by catechol methylation with dimethyl sulfate, methylsulfuric acid or methanol:

    guaiacol synthesis from catechol

Uses.

  • Guaiacol is a source compound in making of flavorings such as eugenol, isoeugenol, santalidol;
  • as an intermediate in synthetic vanillin production;
  • it is used in manufacturing of pharmaceuticals (papaverine, phthivazine and others);
  • in making of stabilizers and antioxidants for plastics and rubbers;
  • as a local anesthetic and antiseptic;

Manufacturer(s) no data
Chemical structure of guaiacol

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