12-04577. Guaiacol Carbonate [Archived]

Nomenclature

CAS number: 553-17-3
Carbonic acid bis(2-methoxyphenyl) ester; guaiacol carbonic acid neutral ester; carbonic acid guaiacol ether; Duotal.
C15H14O5; mol wt 274.27.
C 65.69%, H 5.14%, O 29.17%.

Description and references

Prepd by the action of phosgene on a concd soln of guaiacol in aq NaOH: DE 58129 (to Bayer); S. P. Schotz, Synthetic Organic Compounds (London, 1925) p 137; J. Schwyzer, Die Fabrikation pharmazeutischer und chemisch-technischer Produkte (Berlin, 1931) p 212; H. P. Kaufmann, Arzneimittel-Synthese (Springer-Verlag, 1953) p 607.

Chemical structure

Properties

Odorless needles from ethanol, mp 88.1°. Faint taste of guaiacol. Practically insol in water. At room temp 1 g dissolves in 60 ml ethanol, 1 ml chloroform, 18 ml ether. Much more sol in hot alcohol, hot benzene, hot chloroform. Slightly sol in liq fatty acids. At 20°, 100 g of glycerol (d 1.2612) will dissolve 0.043 g of guaiacol carbonate. Difficult to hydrolyze. Upon ingestion much is excreted unchanged.

Therapeutic Category

Expectorant.

Therapeutic Category (Veterinary)

Expectorant.

Keywords

Expectorant

Status

This monograph has been retired and is no longer subject to revision or update.