89102-35-2

Basic information

• Product Name: (5R,6S)-5,6-Dihydroxyhexadecanoic acid 1,5-lactone
• Synonyms: (5R,6S)-5,6-Dihydroxyhexadecanoic acid 1,5-lactone;(6R)-6-[(S)-1-Hydroxyundecyl]tetrahydro-2H-pyran-2-one;(6R)-6α-[(S)-1-Hydroxyundecyl]tetrahydro-2H-pyran-2-one;(6R)-Tetrahydro-6-[(S)-1-hydroxyundecyl]-2H-pyran-2-one
• CAS NO: 89102-35-2
• Molecular Formula: C₁₆H₃₀O₃
• Molecular Weight: 0
• Mol File: 89102-35-2.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5R,6S)-5,6-Dihydroxyhexadecanoic acid 1,5-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6S)-5,6-Dihydroxyhexadecanoic acid 1,5-lactone(89102-35-2)
• EPA Substance Registry System: (5R,6S)-5,6-Dihydroxyhexadecanoic acid 1,5-lactone(89102-35-2)

Safety Data

• Hazardous Substances Data: 89102-35-2(Hazardous Substances Data)

Upstream product

• 89163-24-6 (5S,6R)-5,6-dihydroxyhexadecanoic acid 
• 88948-60-1 (5S,6R)-6-(benzyloxy)-5-hexadecanolide 
• 97185-11-0 (5S,6R)-(-)-5,6-O-isopropylidenedioxydecanoic acid 
• 17049-50-2 n-decyl magnesium bromide 
• 89408-87-7 (S)-5-formyl δ-valerolactone 
• 108-05-4 vinyl acetate 
• 89102-35-2 (5R*,6S*)-6-hydroxyhexadecan-5-olide 
• 188576-26-3 4-((4S,5S)-5-Decyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester 
• 188576-31-0 4-((4R,5R)-5-Decyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester 
• 188576-28-5 4-((4S,5S)-5-Decyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester 
• 188576-29-6 4-((4R,5R)-5-Decyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester 
• 125481-80-3 (E/Z)-methyl 5-hexadecenoate 
• 89408-86-6 (+)-(6S)-6-(hydroxymethyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 131064-72-7 4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butanal 

Downstream Products

• 81792-36-1 racemic erythro 6-acetoxy-5-hexadecanolide 
• 89102-36-3 (5R,6S)-6-hydroxyhexadecan-5-olide 
• 85551-39-9 (5R,6S)-6-acetoxy-5-hexadecanolide 
• 85551-42-4 acetic acid (R)-1-((S)-6-oxo-tetrahydropyran-2-yl)undecylester 
• 89102-35-2 (5R*,6S*)-6-hydroxyhexadecan-5-olide 

Relevant articles and documents

Intramolecular S(N)2 ring opening of a cyclic sulfate: Synthesis of erythro-(-)-6-acetoxy-5-hexadecanolide - a major component of mosquito oviposition attractant pheromone

Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-α followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfate 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S,5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield.

Asymmetric total synthesis of all four isomers of 6-acetoxy-5- hexadecanolide: The major component of mosquito oviposition attractant pheromones

An asymmetric total synthesis of (5S,6R)-(+)-erythro-6-acetoxy-5- hexadecanolide 1a has been accomplished from readily available hex-5-yn-1-ol via Shi's asymmetric epoxidation as the key step, in eight steps with an overall yield of 33.5%. In addition, the stereoselective synthesis of all four isomers of 6-acetoxy-5-hexadecanolide 1a-1d were obtained via Sharpless asymmetric dihydroxylation and Mitsunobu reaction as the key steps with overall yields of 16.5-21.2%, respectively.

Production of (5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition pheromone, from the seed oil of the summer cypress plant, Kochia scoparia (Chenopodiaceae)

The oviposition pheromone for the pathogen-vectoring mosquitoes in the genus Culex (Diptera: Culicidae), that is, (5R,6S)-6-acetoxy-5- hexadecanolide, is efficiently synthesized, in admixture with the inactive (5S,6R) enantiomer (~33% w/w), from the fixed oil extracted from the seeds of the summer cypress plant, Kochia scoparia (Chenopodiaceae), cultivated on an industrial scale. Oviposition bioassays using gravid females of Culex quinquefasciatus, a vector of filariasis in human beings, showed that the product was attractive, with activity comparable to that of a pure synthetic sample containing the same amount of the active enantiomer. Production of the pheromone in the form of a biologically active crude material via a cheap and renewable plant suitable for development as a new industrial crop provides the basis for control of Cx. quinquefasciatus and other congeneric vectors of pathogens in resource-poor areas of the world.