52207-99-5

Usage

Uses

Used in Fragrance and Flavor Industry:
CIS-7, CIS-11-HEXADECADIENYL ACETATE is used as a key ingredient in perfumes, soaps, and other cosmetic and personal care products to impart a pleasant and versatile aroma.
Used in Food and Beverage Industry:
In the food and beverage industry, CIS-7, CIS-11-HEXADECADIENYL ACETATE is used to enhance flavor profiles, adding a fruity and sweet taste to various products.
Used in Insect Control Products:
CIS-7, CIS-11-HEXADECADIENYL ACETATE has been studied for its potential insect-repellent properties and is used in some insect control products, providing a natural alternative for pest management.

InChI:InChI=1/C18H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-18(2)19/h6-7,10-11H,3-5,8-9,12-17H2,1-2H3/b7-6-,11-10-

Upstream product

• 126784-39-2 ethyl 3-hydroxy-heptanoate 
• 53042-78-7 11-(Z/E)-Hexadecen-7-yn-1-yl acetate 
• 53042-80-1 (Z)-hexadec-7-yn-11-enyl-1-acetate 
• 53963-10-3 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran 
• 75812-59-8 Acetic acid (Z)-11-(diphenyl-phosphinoyl)-undec-7-enyl ester 
• 75812-60-1 11-(2-tetrahydropyranyloxy)-4Z-undecenyldiphenylphosphine oxide 
• 1448312-21-7 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran 
• 110-62-3 pentanal 
• 75-36-5 acetyl chloride 
• 34335-17-6 7-(2-tetrahydropyranyloxy)heptanal 
• 59499-30-8 (7Z,11Z)-8,12-Hexadecadiensaeure-ethylester 
• 3990-05-4 ethyl 6-formylhexanoate 
• 85416-31-5 (Z)-8-Iodo-1-(2-tetrahydropyranyloxy)-7-octene 
• 85416-28-0 8-Iodo-1-(2-tetrahydropyranyloxy)-7-octyne 

Downstream Products

• 53963-06-7 Z,Z-7,11-hexadecadienyl alcohol 

Relevant academic research and scientific papers

Ti-catalyzed cross-cyclomagnesiation of 1,2-dienes in the stereoselective synthesis of insect pheromones

The Ti-catalyzed intermolecular cross-cyclomagnesiation reaction of aliphatic and oxygenated 1,2-dienes with Grignard reagents was used as the key step to develop facile stereoselective methods for preparation of the major components of citrus leafminer moth (Phyllocnistis citrella) pheromones as well as cotton pink bollworm (Pectinophora gossypiella) and fruit fly (Drosophila melanogaster) attractants.

STEREOSPECIFIC SYNTHESIS OF COMPONENTS OF THE NATURAL SEX PHEROMONE OF Pectinophora gossypiella

A multistage stereospecific synthesis of components of the natural pheromone was realized.Conditions were found for stereospecific trans-reduction of the triple bonds.A procedure was developed for regiospecific dehydrohalogenation of 1,2-dibromoalkanes.Conditions giving the Z and E isomers in ratio of 96 : 4 were found for the Wittig reaction.

OZONOLYSIS OF ALKENES AND THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS XL. SYNTHESIS OF (Z,Z)-, (E,E)-, AND (E/Z,Z/E)-7,11-HEXADECADIEN-1-YL ACETATES - COMPONENTS OF THE SEX PHEROMONE OF PECTINOPHORA GOSSYPIELLA (SAUNDERS)

A new approach is proposed for the synthesis of (Z,Z)-, (E,E)-, and (E/Z,Z/E)-7,11-hexadecadien-1-yl acetates, which are components of the sex pheromone of the pink bollworm (Pectinophora Gossypiella).The method is based on the selective ozonolysis of (Z,Z,Z)-, (E,E,E), and (E,E,Z)-cyclododecatrienes.

SYNTHETIC INVESTIGATIONS IN THE FIELD OF INSECT ATTRACTANTS (SEX ATTRACTANTS). X. SYNTHESIS OF THE ACETATES OF CIS-7,CIS-11- AND CIS-7,TRANS-11-HEXADECADIEN-1-OL, THE SEX PHEROMONES OF THE PINK BOLLWORM MOTH Pectinophora gossypiella S. (LEPIDOPTERA, GELECHIIDAE) AND THE GRAIN MOTH Sit...

The synthesis of the acetates of cis-7,cis-11- and cis-7,trans-11-hexadecadien-1-ol, which are the sex pheromones of the pink bollworm moth Pectinophora gossypiella and the Angoumois grain moth Sitotroga cerealella, and their geometric isomers on the basis of the Wittig reaction and of the unsaturated functionally ω-substituted aldehydes is described.The alkylation of the dilithium derivative of 4-pentyn-1-ol by 2-(6-bromohexyloxy)tetrahydropyran in a mixture of liquid ammonia and THF gave a 40percent yield of 11-(2-tetrahydropyranyloxy)-4-undecyn-1-ol, which was hydrogenated selectively to 11-(2-tetrahydropyranyloxy)-cis-4-undecen-1-ol or was reduced to 11-(2-tetrahydropyranyloxy)-trans-4-undecen-1-ol.Both alcohols were oxidized by pyridinium chlorochromate to 11-(2-tetrahydropyranyloxy)-cis-4-undecenal and 11-(2-tetrahydropyranyloxy)-trans-4-undecenal.The reaction of both aldehydes with amyltriphenylphosphonium bromide under stereocontrolled conditions followed by acetolysis gave the acetates of cis-7,cis-11-, cis-7,trans-11-, trans-7,cis-11-, and trans-7,trans-11-hexadecadien-1-ols and a mixture of the acetates of cis-7,cis-11- and cis-7,trans-11-hexadecadien-1-ol (gossyplure).

A Practical Synthesis of Sex Pheromones of Pink Bollworm: Gossyplure

The practical synthesis of (Z,Z) and (Z,E)-7,11-hexadecadienyl acetates, sex pheromones of pink bollworm (gossyplure) is described.

STEREOSELECTIVE AND VERSATILE APPROACH FOR THE SYNTHESIS OF GOSSYPLURE AND ITS COMPONENTS

Efficient synthetic routes to gossyplure and its components (1a and 1b) were formulated.The three key units viz the alkynol 3, the bromide 5, and the alkanal 13 were derived from easily accessible starting materials.Alkylation of 3 with 5, and subsequent semihydrogenation followed by oxidation, provided the C11-alkenal 8 which was subjected to a stereocontrolled Wittig reaction with a C5-phosphonium salt, to yield directly the disired pheromone (1a + 1b).The synthesis of its individual components involved the manipulation via an acetylenic intermediate, viz the alkynol 14 which was obtained through alkylation of 3.A sequence of well-established reactions on 14, then provided the corresponding (E)- and (Z)-alkenylphosphonium salts which upon a (Z)-specific Wittig olefination with the C7-aldehyde (13), led to the stereoselective synthesis of 1a and 1b.