Guaiacol

  • Guaiacol
  • Catechol monomethyl
  • 2-methoxy -phenol (IUPAC)
  • Methylcatechol
  • 2-hydroxy -anisole
  • 1-hydroxy -2-methoxy -benzene

Colorless to yellowish oily liquid or solid with a characteristic odor

Fixed

1.12 g · cm -3

27-29 ° C

205 ° C.

0.3 mbar ( 30 ° C)

9.98

Poorly in water (10 g · l-1 at 30 ° C)

1.5429 (20 ° C)

Attention

520 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Guaiacol is in guaiac trees occurring phytochemicals, the structurally derived from anisole and phenol.

History

Guaiacol was first produced in 1826 by Otto Unspoiled by the distillation of guaiac resin.

Occurrence

Guaiacol occurs in beechwood and guaiac. Guaiacol is formed in addition to other phenols by thermal or microbial degradation of lignin or phenolic acids (eg, ferulic acid ) and comes in many foods esp. in smoked products before.

Properties

Guaiacol smells smoky medical and tastes sweet. The flavor threshold in water is 3 ppb. With its strong smoky taste guaiacol contributes significantly to the coffee aroma and flavor to smoked foods.

With iron (III ) ions, a green color is produced.

Representation

Guaiacol is produced by methylation of 1,2- dihydroxybenzene by means of dimethyl sulfate. As a byproduct, also the dimethylated product that veratrole forms.

It is feasible from o -anisidine by boiling its diazonium salt.

Use

Guaiacol is used in the fragrance industry for the production of vanillin and in the pharmaceutical industry, for example in drug against bronchial diseases ( guaifenesin ).

CAS registry number PubChem Vapor pressure Dangerous Substances Directive (67/548/EEC) Fagus sylvatica CRC Press Boca Raton, Florida Florida CRC Handbook of Chemistry and Physics Annalen der Physik Digital Object Identifier Integrated Authority File
9011
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