CETALOX，AMBROX DL

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Product Description

Ambrox DL （CETALOX）is a concentrated aromatic ingredient which may be used fragrance compounds according to legal and IFRA guidelines.

Product Detail

CETALOX Basic information

Product Name:	CETALOX，AMBROX DL
Synonyms:	Iridiumether;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;Dod ecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]fur;Ambermor;Tetramethyl perhydronaphthofuran
CAS:	3738-00-9
MF:	C16H28O
MW:	236.39
EINECS:	223-118-6
Product Categories:
Mol File:	3738-00-9.mol

CETALOX 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)

CETALOX 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).