557-61-9Relevant articles and documents
Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer's agent
Zhang, Hong-Yan,Yamakawa, Yu-Ichiro,Matsuya, Yuji,Toyooka, Naoki,Tohda, Chihiro,Awale, Suresh,Li, Feng,Kadota, Shigetoshi,Tezuka, Yasuhiro
, p. 604 - 608 (2014/01/23)
In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)- octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on Aβ(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity.
Synthesis of 1-octacosanol and GC-C-IRMS discrimination of samples from different origin
Cravotto, Giancarlo,Calcio Gaudino, Emanuela,Barge, Alessandro,Binello, Arianna,Albertino, Andrea,Aghemo, Costanza
experimental part, p. 428 - 439 (2010/09/20)
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.
PROCESS FOR THE PREPARATION OF ALIPHATIC PRIMARY ALCOHOLS AND RELATED INTERMEDIATES IN SUCH PROCESS
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Page/Page column 13-14, (2010/11/08)
The invention relates to a new method prepare high-molecular-weight aliphatic linear, straight-chain primary alcohols having between 24 up to and including 32 carbon atoms, comprising the steps of : a. transforming the alcohol group of an α-functionalised-ω-hydroxy linear straight chain alkyl or alkene (i) into an alkoxy-metal complex (ii) b. optionally, followed by a transformation of the α-group into a nucleophilic group, c. followed by a coupling reaction of the component as formed on its α-position. The invention further relates to process for the preparation of such protected alcohols via an organometallic cross coupling reaction or a Wittig reaction and novel intermediates and starting compounds therefore.
METHOD FOR THE PRODUCTION OF PRIMARY LONG-CHAIN ALCOHOLS
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Page/Page column 11-12, (2010/02/15)
The invention relates to a method for the production of linear long-chain alcohols with 20 to 40 carbon atoms by means of a growth reaction with ethylene on aluminium compounds.
PROCESS FOR THE PREPARATION OF ALIPHATIC PRIMARY ALCOHOLS AND RELATED INTERMEDIATES IN SUCH PROCESS
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Page/Page column 9; 13, (2010/02/11)
The invention relates to protected alcohol with formula (R1 - O-)mPG, wherein R1 represents a linear, straight-chain alkyl group having 26-30 C-atoms, m is 1 or 2, and PG, forming an ether group in combination with the -O- of the former primary alcohol, represents a protecting group chosen from the group of substituted methyl, substituted ethyl, substituted benzyl and (substituted) silyl groups with at least one substituent on the Si-atom being not a methyl group, in case m = 1; and a diol protecting group in case m = 2, with the proviso that PG is no saccharide. The invention further relates to process for the preparation of such protected alcohols via an organometallic cross coupling reaction.
PROCESS FOR THE PREPARATION OF ALIPHATIC PRIMARY ALCOHOLS AND INTERMEDIATES IN SUCH PROCESS
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Page/Page column 13, (2010/02/11)
The invention relates to protected unsaturated alcohol with formula (R1 - O-)mPG, wherein R1 represents a linear, straight-chain aliphatic hydrocarbon group containing one or more double bonds and having 26-30 C-atoms, m is 1 or 2 and PG, forming an ether group in combination with the -O- of the former primary alcohol, represents a protecting group chosen from the group of substituted methyl ethers, substituted ethyl ethers, (substituted) benzyl ethers and (substituted) silyl ethers with at least one substituent on the Si-atom being not a methyl group, in case m=1; and a diol protecting group in case m=2; A protected saturated alcohol with formula (R2 - O -)mPG, herein R2 represents a linear straight-chain alkyl group with 26-30 C-atoms and PG and m are as defined above; unsaturated alcohols with formula R1OH wherein R1 represents a linear, straight-chain aliphatic hydrocarbon group containing one, two or three double bonds and having 27 C-atoms, a linear, straight-chain aliphatic hydrocarbon group containing one or more double bonds and having 28 C-atoms with the proviso that when R1 has one double bond which is between C18 and C19 or between C19 and C20, R1OH has the E-configuration, or a linear, straight-chain aliphatic hydrocarbon group containing two or three double bonds and having 26-29 C-atoms. The invention further relates to processes for the preparation of such protected unsaturated alcohols via an organometallic cross coupling reaction, a Wittig reaction via Olefin Cross Metathesis.
A PROCESS FOR PREPARING LONG CHAIN SATURATED OR UNSATURATED OXYGENATED COMPOUNDS
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Page 16, (2008/06/13)
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.
Arundinoside B, a new acylated glucoside from Chlorophytum arundinaceum
Tandon, Mamta,Shukla
, p. 988 - 989 (2007/10/03)
A new acylated glucoside, arundinoside B, isolated from the roots of Chlorophytum arundinaceum has been characterised as 1-O-(β-D-3-benzoylglucopyranosyl]octacosanol (1) by spectral and chemical evidence.
Synthesis of even C24-C30 primary normal aliphatic alcohols from cyclododecanone
Zakharkin, L. I.,Churilova, I. M.,Anikina, E. V.
, p. 65 - 67 (2007/10/02)
A simple method has been developed for the oxidation of cyclododecanone by sodium persulfate in an aqueous methanol solution of sulfuric acid to give 12-hydroxydodecanoic acid, which upon treatment with HBr in acetic acid gives 12-bromododecanoic acid with RMgX, where R=C12H25, C14H29, C16H33, and C18H37 in THF in the presence of Li2CuCl4 and subsequent reduction of the salts of the alkanecarboxylic acids by LiAlH4 give primary even normal C24-C30 alcohols.
