17278-80-7

Usage

Synthesis Reference(s)

Tetrahedron, 34, p. 595, 1978 DOI: 10.1016/0040-4020(78)80058-1

InChI:InChI=1/C16H30O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h1,3,17H,2,4-15H2,(H,18,19)/b3-1+

Upstream product

• 533-87-9 threo-9,10,16-trihydroxyhexadecanoic acid 
• 6949-98-0 9,10,16-trihydroxyhexadecanoic acid 
• 18941-99-6 16-Hydroxy-hexadecin-⁽⁹⁾-saeure 
• 533-87-9 DL-threo-9RS,10RS,16-trihydroxyhexadecanoic acid 
• 629-03-8 1 ,6-dibromohexane 
• 4224-70-8 6-bromohexanoic acid 
• 10297-09-3 oct-7-ynoic acid 
• 18458-50-9 7-octynoic acid methyl ester 
• 17696-11-6 8-bromooctanoic acid 
• 6557-85-3 6-bromohexyl malonic acid diethyl ester 
• 57818-67-4 methyl 16-bromohexadec-9-enoate 
• 533-87-9 erythro-9,10,16-trihydroxyhexadecanoic acid 
• 10030-73-6 (E)-9-hexadecenoic acid 
• 871-91-0 oct-7-yn-1-ol 

Downstream Products

• 57491-61-9 16-Tosyloxy-9-hexadecensaeure 
• 54045-02-2 (3S,3aS,4S,7R,8S,8aS)-3-Formyl-4-((Z)-16-hydroxy-hexadec-9-enoyloxy)-8-hydroxymethyl-8-methyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methano-azulene-6-carboxylic acid 
• 124395-03-5 Toluene-4-sulfonic acid (E)-pentadeca-7,14-dienyl ester 
• 88109-73-3 9-hexadecyn-1-ol 
• 10378-01-5 palmitoleyl alcohol 
• 35507-72-3 (E)-1,8-pentadecadiene 
• 84042-37-5 Methyl 16-tosyloxy-(E)-9-hexadecenoate 
• 28645-51-4 (10E/Z)-oxacycloheptadec-10-en-2-one 
• 506-13-8 16-hydroxyhexadecanoic acid 
• 533-87-9 threo-9,10,16-trihydroxyhexadecanoic acid 
• 533-87-9 erythro-9,10,16-trihydroxyhexadecanoic acid 

Relevant academic research and scientific papers

Simple and facile synthesis of (E)-9-hexadecen-1,16-olide (isoambrettolide) and dimethyl (E)-2-undecen-1,11-dioate, a juvenile hormone

(E)-9-Hexadecen-1,16-olide (isoambrettolide) possessing musk-like odour is used as fixative in perfumery formulations. It has been synthesized from threo-aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) by simple procedure. The compound showed antibacterial activity. Synthesis of dimethyl (E)-2-undecen-1,11-dioate was achieved for the first time from threo-aleuritic acid, the major component of lac resin, and its bioassay has been reported.

Bacterial CYP153A monooxygenases for the synthesis of omega-hydroxylated fatty acids

CYP153A from Marinobacter aquaeolei has been identified as a fatty acid ω-hydroxylase with a broad substrate range. Two hotspots predicted to influence substrate specificity and selectivity were exchanged. Mutant G307A is 2- to 20-fold more active towards fatty acids than the wild-type. Residue L354 is determinant for the enzyme ω-regioselectivity.

Probing structure/affinity relationships for the Plasmodium falciparum hexose transporter with glucose derivatives

A series of 3-O-substituted glucose derivatives was prepared with alkyl, alkenyl, aromatic and ferrocenic substituents; to vary lipophilicity and hydrogen bonding ethylenedioxy and perfluorinated fragments were also introduced. Apparent affinities for the Plasmodium falciparum hexose transporter (PfHT) were determined after heterologous expression in Xenopus oocytes, with highest affinities for compounds with C8-C13 lipophilic chains. As no derivatives show significant affinity for the mammalian glucose transporter (GLUT1), these structure/affinity assays contribute to design of potent PfHT inhibitors and eventual development of antimalarials.

Studies on desulphurisation of epithio derivatives of isomeric aleuritic acid and their corresponding dihydroxy dioic acids

(Z) and (E)-Epithio derivatives of isomeric aleuritic acids (9,10,16-trihydroxyhexadecanoic) and 9,10-dihydroxyhexadecane-1,16-dioic acids have been synthesised. Their desulphurisation with iodine yielded corresponding unsaturated acids without any change in configuration.

Acides gras marques en position ω par un nucleide radioactif emetteur γ

The synthesis of many saturated, acetylenic, olefinic (Z or E) fatty acids labeled with 123I or 131I at the ω-position has been achieved.The radioactive iodine atom is introduced by a I-, *I- exchange reaction; the influence on the yield of several parameters - presence of iodine carrier, fatty acid and water concentrations, solution acidity - has been studied.Experimental conditions which produce labeling yields higher than 95percent have been defined; these results have lead to a very easy labeling method used in several hospitals in the external study of myocardial metabolism of fatty acids.

Phosphonium Iodide in Organic Synthesis

Phosphonium iodide is found useful in the stereospecific conversion of some vicinal diols to olefins.Synthesis of cis-hexadec-9-enolide has been achieved.

A Convient Synthesis of (Z)-9-Hexadecen-1-yl Acetate, a Sex Pheromone of Rice Green Caterpillar, Naranga aenescens, from Aleuritic Acid

Aleuritic acid (2) is converted into the 16-hydroxyolefinic acid (3) via ethyl orthoformate reaction and pyrolysis.The methyl ester (4) of (3) on mesylation followed by lithium aluminium hydride reduction gives the olefin alcohol (6).This is converted into Z-olefin alcohol (9) via the acetylene route and acetylated to afford the desired pheromone (1)