70286-33-8

Upstream product

• 24163-93-7 (Z,Z)-farnesyl bromide 
• 870-63-3 prenyl bromide 
• 121881-29-6 (R)-4-((E)-2-Methanesulfonyl-1-methyl-vinyl)-1-methyl-cyclohexene 
• 121881-34-3 1-[(E)-2-((R)-4-Methyl-cyclohex-3-enyl)-prop-1-ene-1-sulfonyl]-propan-2-one 
• 5989-27-5 D-limonene 
• 372-97-4 farnesyl pyrophosphate 
• 86803-80-7 (R)-(+)-1,1'-bi-2-naphthol (Z,Z)-monofarnesyl ether 
• 7212-44-4 (+/-)-nerolidol 
• 40716-66-3 (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol 
• 3790-71-4 (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol 

Relevant academic research and scientific papers

Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol

Heteropoly acid H3PW12O40 is an active and environmentally friendly homogeneous catalyst for the synthesis of α-bisabolol, a high-priced and highly demanded ingredient for the fragrance, cosmetic and pharmaceutical industries, starting from more abundant biomass-based sesquiterpenic alcohols. The solvent nature remarkably affects the reaction pathways and product selectivity. In acetone solutions, α-bisabolol can be obtained in 55-60% GC yields from nerolidol and 60-70% GC yields from farnesol at complete substrate conversions, which are probably the best results ever reported for these reactions. α-Bisabolol synthesized by this method contains no farnesol, which is a potentially allergenic compound and should be avoided in the commercially used α-bisabolol. This advantage is especially important because the distillative separation of α-bisabolol and farnesol is a troublesome task. The catalyst shows high turnover numbers and operates under mild nearly ambient conditions.

PROCESS FOR REMOVING FARNESOL FROM MIXTURES WITH ALPHA-BISABOLOL

Process for esterification of farnesol in an initial mixture comprising alpha-bisabolol, farnesol and optionally other components, with the following steps: 1. Preparation or production of the initial mixture, 2. Adding (i) a transesterification catalyst and (ii) one or more compounds of formula (B) [in-line-formulae]R2YnCO2R1??(B) [/in-line-formulae] in which the following applies: R1 stands for an alkyl residue with 1 to 12 C atoms; R2 stands for hydrogen, an alkyl residue with 1 to 20 C atoms, a cycloalkyl residue with 5 to 20 C atoms, an aryl residue with 6 to 20 C atoms or a heteroaryl residue with 5 to 20 C atoms; and Y stands for CH2, CH(Me), CH(Et), C(Me)2, CH2—CH(Me), CH(Me)-CH2 or CH2—CH(Me)-CH2 and n stands for a whole number from 0 to 6; or R2 stands for a group CO2R3, R3 standing for an alkyl residue with 1 to 12 C atoms; and Y stands for CH2, CH(Me), CH(Et), C(Me)2, CH2—CH(Me), CH(Me)-CH2 or CH2—CH(Me)-CH2 and n stands for a whole number from 0 to 8, or Y stands for an optionally substituted phenyl or naphthyl ring with a total of at most four substituents on the ring, n=1 applying.

CYCLIZATION OF SOME LINEAR TERPENOLS INITIATED BY "ACTIVATED" DMSO

It was shown that the acylhydroxysulfonium salt generated in situ from DMSO and trifluoroacetic anhydride causes low-temperature cyclization of geraniol, linalool, and nerol in an aprotic medium to a mixture of p-menthane monoterpenoids, and the maximum yield is obtained in the case of the last two terpenols.A similar result was obtained for E-nerolidol.

A New Method for C-C Coupling of Terminal Alkenes via a Sulphonylation-Alkylation-Desulphinylation Sequence: Synthesis of E- and Z-α-Bisabolenes

A new method for regiospecific C-C coupling of terminal alkenes based on a sulphonylation-alkylation-desulphinylation process, mediated through allylic sulphinic acids, and its application to the conversion of limonene into E- and Z-α-bisabolenes, are described.