Beta Damascone

Product Name:

Beta Damascone

Synonyms:

2-Buten-1-one, 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-;B-Damascone;1-(2,6,6-Trimethyl-1-cyclohexenyl)-2-butene-1-one;1-(2-Butenoyl)-2,6,6-trimethyl-1-cyclohexene;3,4-Dihydro-3,4,7-megastigmatrien-7-one;BETA-DAMASCONE;BETA-DAMASCONE

CAS:

35044-68-9

MF:

C13H20O

MW:

192.3

Mol File:

35044-68-9.mol

Boiling point 

271.2±10.0 °C(Predicted)

density 

0.907±0.06 g/cm3(Predicted)

FEMA 

3243 | 1-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-2-BUTEN-1-ONE

JECFA Number

384

EPA Substance Registry System

2-Buten-1-one, 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)- (35044-68-9)

Chemical Properties

Beta-Damascone is a colorless to pale yellow liquid with a very powerful floral, complex fruity note, reminiscent of plum, rose, and blackcurrant. ??-Damascone is found as a volatile constituent of many natural materials, for example, in rose oils and extracts.
One synthetic route to the damascones starts with an appropriate cyclogeranic acid derivative (halide, ester, etc.). This is reacted with an allyl magnesium halide to give 2,6,6-trimethylcyclohexenyl diallyl carbinol, which on pyrolysis yields the desired l-(2,6,6-trimethylcyclohexenyl)-3-buten-l-one. Damascone is obtained by rearrangement of the double bond in the side chain.
The ??- and ??-damascones are used in perfume compositions, especially rose perfumes, and in flavor compositions, to which they impart naturalness and body.

Preparation

Various methods: recently from ionone izoxazoles, also from 7,8-dehydro-β-ionole.

Aroma threshold values

Detection: 8.6 to 41 ppb

Taste threshold values

Taste characteristics at 30 ppm: green, woody, minty with a herbal floral nuance.