67587-22-8

Usage

Uses

Used in Flavor and Fragrance Industry:
Methyl octadec-2-ynoate is used as a flavoring agent and fragrance component for its fruity and floral scent. It is ideal for use in perfumes, soaps, and other scented products due to its pleasant aroma.
Used in Food Industry:
Methyl octadec-2-ynoate is used as a food additive to impart a fruity flavor in various food products, enhancing their taste and appeal to consumers.
Used in Pharmaceutical Industry:
Methyl octadec-2-ynoate has potential pharmaceutical applications, as it has been found to exhibit anti-inflammatory and anti-tumor properties. Its therapeutic potential is currently being explored for the development of new treatments.
Overall, methyl octadec-2-ynoate is a versatile compound with applications in various industries, including flavor and fragrance, food, and pharmaceutical sectors. Its safe use in food and consumer products, along with its potential health benefits, make it a valuable ingredient in these industries.

Upstream product

• 112-67-4 n-hexadecanoyl chloride 
• 26186-00-5 1-heptadecyne 
• 79-22-1 methyl chloroformate 
• 173473-44-4 Methyl 3-oxo-2-(triphenylphosphoranylidene)octadecanoate 

Downstream Products

• 65446-29-9 2-methoxy-6-pentadecyl-benzoic acid methyl ester 
• 17257-37-3 methyl octadec-cis-2-enoate 
• 16611-84-0 6-Pentadecylsalicylic Acid 
• 38449-27-3 6-pentadecylsalicylic acid methyl ester 

Relevant academic research and scientific papers

Ralstonins A and B, Lipopeptides with Chlamydospore-Inducing and Phytotoxic Activities from the Plant Pathogen Ralstonia solanacearum

Ralstonia solanacearum has an orphan hybrid polyketide synthase-nonribosomal peptide synthetase gene cluster. We herein isolate its products (named ralstonins A and B) from R. solanacearum and elucidate their structures and biological activities. Ralstonins are unusual lipodepsipeptides composed of 11 amino acids (containing unique amino acids such as β-hydroxytyrosine and dehydroalanine) and a 3-amino-2-hydroxyoctadecanoic acid, and their production is controlled by quorum sensing, a mechanism of bacterial cell-cell communication. Ralstonins exhibited chlamydospore-inducing activity and phytotoxicity.

Synthesis of Anacardic Acids

The anacardic acids 1-11, isolated from various plants, were synthesized by a new general method.Reaction of the methyl alkynoates 12-18 with 1-methoxy-1,4-cyclohexadiene at 200 deg C afforded directly the methyl 2-methoxybenzoates 19-25 with long chain substituents in 6-position in 74-85percent yield.The dienophiles 12-16 were prepared by pyrolysis of the corresponding acylphosphoranes 26-30, the dienophiles 17 and 18 by methoxycarbonylation of the corresponding alkynes 31 and 32 via the hydroxy esters 33 and 34.Demethylation of 19-23 with AlI3 gave the methyl salicylates 35-39 which could be hydrolized to the anacardic acids 1-4 and 7.Hydrolysis of 24 and 25 provided the hydroxy acids 40 and 41, which were converted by treatment with CBr4/PPh3 into the acids 42 and 43 bearing bromoalkyl side chains.These were transformed into 44-47 by reaction with 1-hexynyllithium and 1-octynyllithium.Stereoselective hydrogenation of 44-47 gave 48-51 with (Z)-alkene side chains.In a similar approach 42 was converted into 52 and then into 53, which gave upon treatment with 1-pentynylmagnesium bromide or 1-heptynylmagnesium bromide the acids 54 and 55 with alkadiyne side chains.Stereoselective hydrogenation provided 56 and 57 with (Z,Z)-alkadiene side chains.The 2-methoxy group in 48-51, 56, 57 was demethylated by treatment with AlI3 to give the anacardic acids 5, 6, 8-11. - Keywords: Anacardic acids; Benzoates, methyl 6-alkyl-2-methoxy-; 2-Alkynoates, methyl; Aluminium triiodide, demethylation by treatment with