| Identification | Back Directory | [Name]
AMBROX DL | [CAS]
3738-00-9 | [Synonyms]
Cetalox
AMBERLYN
Ambermor
AMBROX DL
Ambraoxide
AMBERLYN 50
Iridium ether
amber naphthofuran
AMBROX DL, FIRMENICH
Tetramethyl perhydronaphthofuran
Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]fur
3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan
Dodecahydro-3a,6,6,9a-tetramethylnaphtol[2,1-b]furan
1-b]furan,dodecahydro-3a,6,6,9a-tetramethyl-naphtho[
Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan
Naphtho2,1-bfuran, dodecahydro-3a,6,6,9a-tetramethyl-
1-b]furan,dodecahydro-3a,6,6,9a-tetramethyl-Naphtho[2
DODECAHYDRO-3A,6,6,9A-TETRAMETHYLNAPHTO-(2,1-B)-FURAN
(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan
3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e]benzofuran
3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran | [EINECS(EC#)]
223-118-6 | [Molecular Formula]
C16H28O | [MDL Number]
MFCD06799381 | [MOL File]
3738-00-9.mol | [Molecular Weight]
236.39 |
| Hazard Information | Back Directory | [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. | [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 | [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). |
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