57221-93-9

Upstream product

• 3639-35-8 10-hydroxydecanoic acid ethyl ester 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 22054-14-4 8-hydroxyoctanal 
• 21573-31-9 oct-7-enal 
• 57221-80-4 8-tetrahydropyranyloxyoctanal 
• 57221-92-8 ethyl (E)-10-(2-tetrahydropyranyloxy)-2-decenoate 
• 78426-45-6 ethyl (2E)-2,9-decadienoate 
• 64971-11-5 10-Hydroxy-4-decensaeureethylester 
• 64971-10-4 4,9-Decadiensaeureethylester 
• 25017-00-9 2-Acetyl-deca-4,9-diensaeure-aethylester 

Downstream Products

• 14113-05-4 (E)-10-hydroxy-dec-2-enoic acid 
• 765-01-5 10-hydroxy-2-decenoic acid 

Relevant academic research and scientific papers

Method for the preparation of unsaturated hydroxy fatty acids and their esters, their use in pharmaceutical and/or cosmetic preparations

A method of preparing unsaturated hydroxy fatty acids and esters thereof corresponding to general formula (Id): wherein n=1 to 4, m=2 to 16, R1═OH, Cl, Br, OR3 in which R3 is a straight or branched alkyl, alkenyl or alkynyl radical of 1 to 16 carbons or glycerol esters, optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, R2═H, SiR′1R′2R′3 in which R′1, R′2 and R′3 can be identical or different from each other and are a straight or branched alkyl, alkenyl or alkynyl radical of 1 to 16 carbons or glycerol esters, optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, or R2═C—Ar3 with Ar representing an aryl radical optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, or R2=the tetrahydropyranyl of formula: is disclosed.

Synthesis of (E)-9-oxo-2-decenoic acid and (E)-10-hydroxy-2-decenoic acid

Syntheses of (E)-9-oxo-decenoic acid (III), queen's substance and (E)-10-hydroxy-2-decenoic acid (V), a componenet of royal jelly and a bee pheromone, have been accomplished through a common intermediate (I).

WITTIG-HORNER REACTION IN HETEROGENOUS MEDIA VII. A NEW STRATEGY FOR THE TOTAL SYNTHESIS OF THE ROYAL JELLY ACID AND THE QUEEN SUBSTANCE OF HONEY-BEE

A new general scheme for the preparation of Royal Jelly acid and Queen Substance of honey-bee, including, as the key steps, copper I catalyzed addition of functional (protected alcohol and ketone) Grignard reagents to acrolein diethylacetal, and the Wittig-Horner reaction of unprotected 8-hydroxyoctanal and 7-oxo-octanal with triethylphosphonoacetate in water, in the presence of potassium carbonate.

LA REACTION DE WITTIG-HORNER EN MILIEU HETEROGENE VI. SELECTIVITE DE LA REACTION SUR DES COMPOSES BIFONCTIONNELS

Heterogenous media of low basicity (K2CO3 or KHCO3), liquid-liquid or solid-liquid allow the Wittig-Horner reaction of fragile and unprotected aldehydes (hydroxyaldehydes, nitroaldehyde and ketoaldehydes) with excellent yields.The reaction is applied to the synthesis of Royal Jelly acid and Queen Substance of Honey bee.

Mechanism of Formation of α,β-Unsaturated Esters in the Reaction of Ethyl Mercaptoacetate Dianion with Carbonyl Compounds

Dianion derived fron ethyl mercaptoacetate undergoes aldol type reaction with a carbonyl compounds to give an adduct, which exhibited low diastereoselectivity.However, the adducts obtained by the reaction with a variety of aldehydes were subsequently treated with ethyl chloroformate in the presence of trivalent phosphorus compound to give (E)-isomers of α,β-unsaturated esters in high yields with greater than 85percent stereoselectivity regardless of the stereochemistry of the diastereomers of the adducts.The stereochemical mechanism and application of this reaction were studied in detail.