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| | AMBROX DL Basic information |
| Product Name: | AMBROX DL | | Synonyms: | 1-b]furan,dodecahydro-3a,6,6,9a-tetramethyl-Naphtho[2;Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan;AMBROX DL;DODECAHYDRO-3A,6,6,9A-TETRAMETHYLNAPHTO-(2,1-B)-FURAN;Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]fur;Tetramethyl perhydronaphthofuran;Naphtho2,1-bfuran, dodecahydro-3a,6,6,9a-tetramethyl-;AMBROX DL, FIRMENICH | | CAS: | 3738-00-9 | | MF: | C16H28O | | MW: | 236.39 | | EINECS: | 223-118-6 | | Product Categories: | | | Mol File: | 3738-00-9.mol |  |
| | AMBROX DL Chemical Properties |
| | 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 Preparation Products And Raw materials |
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