62972-93-4

Usage

Uses

Used in Pheromone Synthesis:
11-OCTADECYN-1-OL is used as a key intermediate in the synthesis of cis-Vaccenyl acetate, a female-produced sex attractant pheromone component of the cerambycid beetle Ortholeptura valida (LeConte). This pheromone plays a crucial role in the mating behavior of these beetles, and the compound is essential for the production of this biologically active substance.
Used in Chemical Research:
Due to its unique structure and properties, 11-OCTADECYN-1-OL can be used as a starting material or a building block in the synthesis of various other organic compounds. It can be particularly useful in the development of new chemicals with potential applications in pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Analytical Chemistry:
11-OCTADECYN-1-OL can also be employed as a reference material or a standard in analytical chemistry for the identification and quantification of similar compounds. Its unique properties make it a valuable tool for researchers working on the development of new analytical methods and techniques.

Upstream product

• 65734-26-1 octadeca-1,11c-diene 
• 6198-58-9 methyl (Z)-vaccenate 
• 86426-74-6 octadec-11-ynal 
• 55695-90-4 2-(9-bromononyloxy)tetrahydropyran 
• 76070-19-4 11-((tetrahydro-2H-pyran-2-yl)oxy)undecanal 
• 108536-01-2 (Z)-8-(tetrahydro-2H-pyran-2-yloxy)oct-4-enyl 4-methylbenzensulfonate 
• 62422-46-2 (Z)-8-<(tetrahydropyran-2-yl)oxy>oct-4-enol 
• 56506-08-2 (Z)-oct-4-ene-1,8-diol 
• 10160-24-4 7-bromoheptyl alcohol 
• 629-30-1 1,7-heptandiol 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 10160-25-5 7-bromo-1-(2-tetrahydropyranyloxy)heptane 
• 21676-07-3 (Z)-undec-4-en-1-ol 
• 13423-48-8 triphenylheptylphosphonium bromide 

Downstream Products

• 648880-73-3 (Z)-octadec-11-enyl methanesulfonate 
• 4273-95-4 (Z)-11-octadecenal 
• 6186-98-7 (Z)-11-octadecen-1-yl acetate 

Relevant academic research and scientific papers

Isolation, identification, and synthesis of sex pheromone components of female tea cluster caterpillar, andraca bipunctata walker (lepidoptera: bombycidae) in Taiwan

Octadecanal (18: Ald), (E)-11-octadecenal (E11-18: Ald). (E)-14-octadecenal (E14-18:Ald) and (E, E)-11,14-octadecadienai (E11,E14-18: Ald) were isolated and identified as major components from the pheromone glands of the tea cluster caterpillar, Andraca bipunctata, in Taiwan by analyzing the mass spectra of gland components and their DMDS adduces. GC retention times and mass spectra of the components were in agreement with those of authentic synthetic compounds. The average amount of 18 : Ald, E11-18:Ald. E14-18:Ald and E11,E14-18:Ald per female gland (1 to 3 days old) was 121 ± 76, 50 ± 20. 187 ± 75. and 237 ± 110 ng. respectively, in a ratio of 20:8:31:41. Synthetic E11, E14-18:Ald caught more males than each of the other three components or blank control in field trapping tests. E11, E14-18 : Aid is reported as an insect sex pheromone for the first time. Male antenna responded to E11, E14-18: Ald strongly in an EAG analysis. Furthermore, 4 hr after the injection of PBAN (pheromone biosynthetic activating neuropeptide) into decapitated female moths (2 days old), the percentage of the E11, E14-C18 Ald in the gland extract increased from 0% to 75.5%, which was also significantly more than that of unligaled and uninjected control at 55.1%. All these data indicated that E11, E14-18:Ald is the sex pheromone of the Andraca bipunctuta in Taiwan. Plenum Publishing Corporation.

Remarkable regioselective hydroboration of terminal alkenes by calcium borohydride

Calcium borohydride is found to hydroborate unsaturated systems in the presence of ethyl acetate. The reaction exhibits remarkable selectivity towards terminal double bonds. Several Z-11-alken-1-ol pheromones are synthesized using this method.

Synthesis of Z-11-octadecenal, the sex pheromone of the wax moth

A new synthesis of Z-11-octadecenal, the sex pheromon of the wax moth Achroia grisella starting from the methyl 10-undecenoate is elaborated. - Key words: insect pheromone, stereoselective synthesis; Wittig reaction; hydroboration.

Synthesis of (E,E)-10,12-hexadecadienal and (Z)-11-octadecenal

Two economically important insect pheromones, viz. (E,E)-10,12-hexadecadien-1-al (1) and (Z)-11-octadecenal (2) of cotton pests have been synthesised from cheap and readily available materials utilising in situ alkylation of dianion of 4-pentyn-1-ol obtainable easily by lithium amide induced opening of tetrahydrofurfuryl chloride in liquid ammonia.

INSECT PHEROMONES AND THEIR ANALOGS III. SYNTHESIS OF THE SEX ATTRACTANTS OF SOME LEPIDOPTERA

A new route to the synthesis of a number of attractants of Lepidoptera (Argyrotaenia velutinana, Mamestra configurata, and Lycorea ceres ceres) have been developed.These substances are acetates of enols with the cis configuration: tetradec-11-en-1-ol, hexadec-11-en-1-ol, and octadec-11-en-1-ol, respectively.The constants of the substances obtained agree completely with those given in the literature.The method is based on the coupling of the C3, C5, and C7 aldehydes with methyl 11-bromoundecanoate (I) by the Wittig reaction.To obtain compound (I) from methyl undeca-2E,5E,10-trienoate or methyl undeca-10-enoate we used hydroboration according to Brown followed by hydrogenation and bromination of the alcohol obtained.The advantage of this method is the use as starting materials of esters of unsaturated acids readily obtained by the homogeneous catalytic co-oligomerization of 1,3-dienes with acrylates.