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.
Uses
This ingredient provides warmth, richness and elegance to all areas of perfumery from sheer florals to modern ambers. Due to its power, best effects can be achieved at lower dosages, however, higher levels are often used to provide performance and substantivity.
Definition
ChEBI: Ambronide is a naphthofuran.
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
General Description
AMBROX DL is an elegant amber-based fragrance note with rich woody characteristics. This substance is typically solid at room temperature and consists of a blend of approximately 30 per cent of the proprietary ingredient Cachalox® and 70 per cent Cetalox (9-epi-Ambrox). Owing to its long-lasting fragrance and high stability, it is frequently used in personal care products. It has also become the fragrance of choice for perfumes with pronounced woody undertones.
Trade name
Compound starting from natural sclareol: Ambermore,
Ambermore-DL, Ambermore-EX (Aromor), Ambrox® Super (Firmenich),
Ambroxide® (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).
