Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan

AMBROX DL Chemische Eigenschaften,Einsatz,Produktion Methoden

• Chemische Eigenschaften

  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.

• synthetische

  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

• Handelsname

  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 Upstream-Materialien And Downstream Produkte

Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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