3879-60-5

Usage

Definition

ChEBI: The (2E,6Z)-stereoisomer of farnesol.

Upstream product

• 19317-11-4 farnesal 
• 4602-84-0 farnesol 
• 64-18-6 formic acid 
• 7212-44-4 (+/-)-nerolidol 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 20085-73-8 ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate 
• 19954-66-6 ethyl 3,7,11-trimethyl-2ξ,6Z,10-dodecatrienoate 
• 50-00-0 formaldehyd 
• 3879-26-3 (Z)-nerylacetone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 80767-64-2 p-nitrobenzoate de trimethyl-3,7,11 dodecatriene-1,6 Z, 10-yl 
• 59830-37-4 1-phenylsulfonyl-2-methyl-4-hydroxy-but-2-ene 
• 61194-08-9 chlorure de geranylmagnesium 

Downstream Products

• 6750-34-1 (3R,7R)-hexahydrofarnesol 
• 156848-67-8 C₂₂H₂₉BrO₃ 
• 28624-23-9 2,3,4,4a,5,6-hexahydro-1,4a-dimethyl-7-(1-methylethyl)-naphthalene 
• 469-61-4 (+/-)-cedrene 
• 5975-30-4 epizonarene 
• 104746-49-8 (1S,2R)-5,5-dimethyl-2-(6-methylhepta-1,5-dien-2-yl)cyclohexanol 

Relevant academic research and scientific papers

PRODUCTION OF FARNESOL

The present invention relates to an improved way for the production of farnesol.

Method for Converting Farnesol to Nerolidol in the Presence of Alpha-Bisabolol

A method for converting farnesol to nerolidol in the presence of alpha-bisabolol including providing or preparing a mixture of alpha-bisabolol, farnesol, and one or more catalysts for selective isomerization of farnesol to nerolidol in the presence of alpha-bisabolol, and converting at least a portion of the farnesol to nerolidol.

Synthesis of farnesol isomers via a modified wittig procedure

(Chemical Equation Presented) The four olefin stereoisomers of farnesol have been synthesized from readily available nerylacetone or commercial geranylacetone. A new variation on the use of β-oxido ylides favored the (2Z)-stereoisomers, whereas the (2E)-isomers were obtained through a classical Horner-Wadsworth-Emmons condensation with triethyl phosphonoacetate and reduction of the resulting ester.

Stereospecific synthesis and biological evaluation of farnesyl diphosphate isomers

(Matrix presented) A unified, stereospecific synthetic route to the three geometric isomers of (E,E)-farnesyl diphosphate (E,E-FPP) (1,2, and 3) has been developed. The key feature of this synthesis is the ability to control the stereochemistry of triflation of the β-ketoester 10 to give either 11 or 14. Preliminary evaluation of these compounds with protein-farnesyl transferase indicates that 1 and 2 are surprisingly effective substrates; however, Z,Z-FPP (3) is a poor substrate and a sub-micromolar inhibitor.

SYNTHESE A L'AIDE DE SULFONES-XXVI. SYNTHESE D'ALCOOLS ALLYLIQUES ET DE POLYPRENOLS PAR ATTACHEMENT D'UN SYNTHON PRENOL EN POSITION 4 E

The E-hydroxyalkylsulphone PhSO2CH2C(CH3)=CHCH2OH is regioselectively and stereoselectively substituted by Grignard reagents in the presence of copper(II) acetylacetonate, giving E allylic alcohols in high yield.A recurrent synthesis of polyprenols and an efficient preparation of the African Monarch pheromone are described.

Sur la stereochimie de la cyclisation du nerolidol an α-bisabolol

The cyclisation of linalyl to α-terpinyl derivatives is known to take place with efficient transfer of chirality.Information was needed about the analogous cyclisation of nerolidyl to bisabolyl derivatives.This was made possible through the recent determination of the absolute configuration of bisabolol and epibisabolol.Hydrolysis of (+)(S) nerolidyl paranitrobenzoate has been carried out under the experimental conditons used for (-)(R) linalyl paranitrobenzoate.Strong asymmetric induction was observed about C4 (in the ring) but very little, if any, about C8 (in the chain).The cyclisation of (+)(S) nerolidol has been brought about by 90/10 aqueous formic acid.Under these experimental conditions very little asymmetric induction is observed about C8 or C4.This is explained by rapid racemisation of the starting material under the cyclisation conditions.