34010-15-6

Usage

Uses

Used in Insect Pheromone Production:
CIS-11-TETRADECEN-1-OL is used as a key component in the production of insect pheromones. It is involved in the biosynthesis process, where acetyltransferases catalyze the formation of acetates from acetyl-CoA and fatty alcohols, such as CIS-11-TETRADECEN-1-OL, to create pheromones that are essential for insect communication and mating.
Used in Chemical Synthesis:
CIS-11-TETRADECEN-1-OL can be used as a starting material or intermediate in the synthesis of various chemical compounds, including fragrances, flavors, and other specialty chemicals. Its unique structure and properties make it a valuable building block for creating a wide range of products.
Used in Research and Development:
As a compound involved in insect pheromone production, CIS-11-TETRADECEN-1-OL is also used in research and development to study the biological processes and mechanisms underlying insect communication, mating behavior, and chemical ecology. This knowledge can be applied to develop novel pest control strategies, improve agricultural practices, and enhance our understanding of insect biology.
Used in Pharmaceutical Industry:
CIS-11-TETRADECEN-1-OL may have potential applications in the pharmaceutical industry, particularly in the development of new drugs targeting insect-related diseases or conditions. Its role in pheromone biosynthesis could provide insights into the development of novel compounds with insecticidal or repellent properties, which could be used to combat insect-borne diseases or control pest populations.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 1141, 1995 DOI: 10.1016/0040-4039(94)02441-D

InChI:InChI=1/C14H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h3-4,15H,2,5-14H2,1H3/b4-3-

Upstream product

• 35289-31-7 dodec-11-en-1-ol 
• 5675-51-4 1,12-dodecandiol 
• 111-81-9 Methyl 10-undecenoate 
• 6287-90-7 11-bromo-undecanoic acid methyl ester 
• 24724-07-0 methyl 11-hydroxyundecanoate 
• 42236-50-0 1,12-diacetoxydodecane 
• 35153-10-7 11-Dodecenyl acetate 
• 1931-65-3 methyl 11-oxoundecanoate 
• 106-98-9 1-butylene 
• 68760-58-7 11-eicosenol 
• 40564-10-1 2-propylidene-cyclopentanone 
• 33925-73-4 13-tetradec-11-yn-1-ol 
• 35148-18-6 (Z)-9-dodecenol 
• 75-21-8 oxirane 

Downstream Products

• 35237-64-0 (Z)-11-tetradecenal 
• 20711-10-8 (Z)-11-tetradecenyl acetate 
• 913964-02-0 3-[(11Z)-tetradec-11-en-1-yl]-1,3-oxazolidine-2,4-dione 
• 3669-80-5 11-hydroxyundecanoic acid 

Relevant academic research and scientific papers

SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES

Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones

Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).

Concise syntheses of insect pheromones using Z-Selective cross metathesis

Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.

SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES

The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.

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 PHEROMONES, IV. CHEMISTRY OF THE WITTIG REACTION, I. EFFECTS OF REACTION CONDITIONS ON THE STEREOSELECTIVITY AND YIELD OF THE WITTIG REACTION

The reactions of nonstabilized triphenylphosphorus ylides with aldehydes have been studied in detail.The stereochemistry and yields of the alkene products are highly dependent upon base used for the generation of the ylide, the solvent and reaction temperature.The synthesis of sex pheromone components by Wittig reaction are also described.

SYNTHESIS OF (Z)-TETRADEC-11-EN-1-OL AND (Z)-HEXADEC-11-EN-1-OL FROM DODECANE-1,12-DIOL

A method have been developed for obtaining (Z)-tetradec-11-en-1-ol and (Z)-hexadec-11-en-1-ol via dodec-11-yn-1-ol.