AMBROX DL
- Product Name
- AMBROX DL
- CAS No.
- 3738-00-9
- Chemical Name
- AMBROX DL
- Synonyms
- Cetalox;Ambermor;AMBERLYN;AMBROX DL;Ambraoxide;AMBERLYN 50;Iridium ether;CETALOX 922560;amber naphthofuran;AMBROX DL, FIRMENICH
- CBNumber
- CB9272233
- Molecular Formula
- C16H28O
- Formula Weight
- 236.39
- MOL File
- 3738-00-9.mol
AMBROX DL Property
- 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)
N-Bromosuccinimide Price
- Product number
- FFG0002227
- Product name
- DODECAHYDRO-3ALPHA,6,6,9ALPHA-TETRAMETHYL-NAPHTHO[2,1-B]FURAN
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $501.47
- Updated
- 2021/12/16
AMBROX DL Chemical Properties,Usage,Production
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).