57243-06-8

Upstream product

• 603-35-0 triphenylphosphine 
• 112-89-0 1-Bromooctadecane 
• 42036-79-3 Phosphonium salt of [1-BROMOOCTADECANE] 

Downstream Products

• 53623-10-2 3,11-dimethylnonacosan-2-one 
• 593-50-0 melissyl alcohol 
• 104410-91-5 7(Z),11(Z)-nonacosadiene 

Relevant academic research and scientific papers

Synthesis of 1-octacosanol and GC-C-IRMS discrimination of samples from different origin

Lately, long-chain primary alcohols have been investigated in depth on account of their biological activities. In particular, 1-octacosanol (C 28H57OH), the main component of policosanol, the hypolipidaemic fatty alcohol mixture obtained from sugar cane wax, has been the subject of a multitude of pharmacological studies. The aim of this work was to search a convenient synthetic protocol for the preparation of 1-octacosanol in a gram scale. The key step was a Wittig reaction between the octadecyltriphenylphosphonium ylide and the methyl 10-oxodecanoate. Some steps were further improved by power ultrasound and microwave irradiation, either alone or in combination. Our methodology is suitable for a rapid generation of homologues by varying the chain length in the alkyl halide. Due to the high commercial value, a series of 1-octacosanol samples, either isolated from natural sources or from synthesis (different origin and suppliers), were analysed by gas chromatography-combustion-isotopic ratio mass spectrometry (GC-C-IRMS) and according to the carbon isotopic content, classified on the basis of their origin.

A PROCESS FOR PREPARING LONG CHAIN SATURATED OR UNSATURATED OXYGENATED COMPOUNDS

A process for preparing long chain saturated or unsaturated oxygenated compounds. The process for the preparation of long-chain saturated or unsaturated oxygenated compounds having from 20 to 36 carbon atoms, selected from the group consisting of polycosanoic acids, their alkyl esters, polycosanols and corresponding compounds having an unsaturated hydrocarbon chain comprises the operation of reacting, in accordance with the Wittig or Peterson olefination reaction, a phosphorus ylide RP(Ar)3, wherein R is a saturated or unsaturated hydrocarbon chain containing one or more ethylenic and/or acetylenic unsaturations and Ar is aryl, or the corresponding α-silylcarbanion, respectively, with an n-alkanoic acid, formylated in the terminal position, or with its corresponding alkyl ester.

An Efficient Synthesis of 1-Triacontanol

Reduction of 12-dodecanolide (1), readily accessible from cyclododecanone, with diisobutylaluminium hydride afforded a 98:2 mixture of 12-hydroxydodecanal (3) and 2-oxa-1-cyclotridecanol (2).Its reaction with triphenyloctadecylphosphorane yielded 12-triaconten-1-ol (4), the catalytic hydrogenation of which gave a total yield of 68percent of 1-triacontanol (5) starting from cyclododecanone.