AMBROX DL Chemical Properties

Melting point:

75-76 °C

Boiling point:

273.9±8.0 °C(Predicted)

Density 

0.939±0.06 g/cm3(Predicted)

FEMA 

3471 | 1,5,5,9-TETRAMETHYL-13-OXATRICYCLO(8.3.0.0(4,9))TRIDECANE

Odor

at 10.00 % in dipropylene glycol. dry woody amber ambergris musk sweet

Odor Type

amber

JECFA Number

1240

LogP

5.41

EPA Substance Registry System

Naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a-tetramethyl- (3738-00-9)

AMBROX DL Usage And Synthesis

Chemical Properties

3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan is a crystalline autoxidation product of ambrein with a typical ambergris odor. It is prepared from (?)-sclareol, a diterpene alcohol obtained from extraction of clary sage plants. Oxidative degradation to a lactone (“sclareolide”), hydrogenation of the latter to the corresponding diol, and dehydration yield the title compound.

Occurrence

Reported found in clary sage oil.

Preparation

Racemic sclareolide can be prepared by cyclization of homofarnesic acid in the presence of SnCl4 as a catalyst . Pure diastereomers are obtained by acid cyclization of (E)- and (Z)-4-methyl-6-(2,6,6-trimethylcyclohex-l(2)-enyl)-3- hexen-1-ol, prepared from 2-methyl-4-(2,6,6-trimethylcyclohex-l(2)-enyl)-2- butenal [394]. If the racemic sclareolide mixture is resolved into its enantiomers, the (–)-oxide may also be obtained by a totally synthetic route

Definition

ChEBI: Ambronide is a naphthofuran.

Synthesis Reference(s)

Synthesis, p. 216, 1983 DOI: 10.1055/s-1983-30287

Trade name

Compound starting from natural sclareol: Ambermore, Ambermore-DL, Ambermore-EX (Aromor), Ambrox® Super (Firmenich), Ambroxan® (Kao), Ambroxide (Symrise); compound starting from homofarnesic acid derivatives: Ambrox® DL (Firmenich); compound starting from 2-methyl- 4-(2,6,6-trimethylcyclohex-l(2)enyl)-2-butenal: Cetalox® (Firmenich), Cetalor (Aromor).

AMBROX DL(3738-00-9)Related Product Information

• Sclareolide
• AMBROX DL
• Ambroxane