35746-21-5

Usage

Uses

Used in Pheromone-based Pest Management:
E-11-TETRADECENAL is used as a pheromone component in pest management strategies, specifically targeting the spruce budworm. By mimicking the natural sex pheromone released by female spruce budworms, E-11-TETRADECENAL can be employed to attract and monitor the presence of male spruce budworms in affected areas. This approach helps in controlling pest populations and reducing the damage caused by these insects to forests and agricultural crops.
Used in Chemical Ecology Research:
E-11-TETRADECENAL is also utilized in chemical ecology research to study the behavior and communication mechanisms of various insect species. Understanding the role of pheromones in insect mating and aggregation can provide valuable insights into the development of novel pest control methods and the conservation of ecosystems.
Used in Fragrance and Flavor Industry:
Due to its unique chemical structure and properties, E-11-TETRADECENAL can be used as a raw material in the fragrance and flavor industry. It can contribute to the development of new scents and flavors, enhancing the sensory experience of various products.

Hazard

Low toxicity by ingestion, inhalation, and skin contact.

InChI:InChI=1S/C14H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h3-4,14H,2,5-13H2,1H3/b4-3+

Upstream product

• 112-45-8 10-Undecenal 
• 112-43-6 10-Undecen-1-ol 
• 59101-18-7 trideca-1,12-dien-3-ol 
• 79-37-8 oxalyl dichloride 
• 35153-18-5 (E)-11-tetradecen-1-ol 
• 71487-11-1 11-tetradecenal diethylacetal 
• 119136-11-7 methyl (E)-11-tetradecenoate 
• 818-88-2 sebacic acid mono methyl ester 
• 33189-72-9 (E)-tetradec-11-en-1-yl acetate 
• 50816-18-7 9-decen-1-yl acetate 
• 401812-65-5 1-tosyloxytetradeca-3E,13-diene 
• 401812-63-3 methyl tetradeca-3E,13-dienoate 
• 401812-62-2 tetradeca-3E,13-dienoic acid 
• 401812-64-4 tetradeca-3E,13-dien-1-ol 

Relevant academic research and scientific papers

Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates

Compounds of the formula (I) wherein R2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.

(E4,Z9)-Tetradecadienal, a sex pheromone for three North American moth species in the genus Saturnia

The lepidopteran genus Saturnia has three representatives in North America, S. walterorum, S. mendocino, and S. albofasciata. (E4,Z9)-Tetradecadienal (E4,Z9-14:Aid) was identified as a sex pheromone component for all three species by combinations of coupled gas chromatography-electroantennogram detection (GC-EAD), GC-mass spectrometry (MS), and field trials. In field trials, all three species were strongly attracted to (E4,Z9-14:Ald) as a single component, Small amounts of (Z)-9-tetradecenal (Z9-14:Ald) also were found in extracts of all three species, but blends of this compound with E4,Z9-14:Aid were no more attractive to male moths than E4,Z9-14:Ald alone. Extracts of pheromone glands of female S. walterorum occasionally contained a third, trace compound eliciting responses from male antennae in GC-EAD experiments, but this compound was not identified. It is suggested that the three species can use the same, single component as a sex attractant because the flight period of S. albofasciata (fall) is different than that of the other two species (spring), whereas the geographic distributions of S. mendocino and S. walterorum overlap over only small portions of their ranges. Furthermore, the latter two species readily hybridize, so there may be minimal fitness cost to cross-attraction.

Stereospecific synthesis of 11E-tetradecenal, 11E-tetradecen-1-ol, and its acetate, pheromone components of insects of Lepidoptera order, from 10-undecenoic acid

A regio-and stereospecific synthesis of 11E-tetradecen-1-ol and its derivatives, which are pheromone components of many insect species of Lepidoptera order, by means of a reaction of methylmagnesium cuprate reagent with 1,12-tridecadien-3-yl acetate by the SN2' mechanism, was carried out.

INSECT PHEROMONES AND THEIR ANALOGUES. XXXVII. SYNTHESIS OF TETRADEC-11E-ENAL AND OF TETRADEC-11E-EN-1-OL AND ITS ACETATE FROM UNDECENOIC ACID

A stereospecific synthesis has been achieved of tetradec-11E-enal and of tetradec-11E-en-1-ol and its acetate - components of the pheromones of many species of insects of the order Lepidoptera - from the readily available undecenoic acid, using the Knoevenagel reaction and catalytic hydroalumination.

SIMPLE SYNTHESIS OF ACETOGENIN TRANSOID INSECT PHEROMONES STARTING FROM ACETYLCYCLOPROPANE

A highly effective synthesis of a series of alkyl and 1-alkenyl cyclopropyl ketones, which are key components in the complete synthesis of a large number of transoid lepidoptera pheromones, has been developed, based on the alkylation of N-cyclohexyl-1-cyclopropylethylideneimine or its condensation with aldehydes.

Acetylcyclopropane as a Five-Carbon Building Block in the Synthesis of some Acetogenin Insect Pheromones

Interaction of deprotonated acetylcyclopropane cyclohexylimine with several aliphatic alkyl halides, epoxides, and aldehydes efficiently gave the corresponding cyclopropyl ketones.Some of the respectible alcohols were rearranged in a highly stereoselective manner under the action of trimethylsilyl bromide in the presence of zinc bromide into the corresponding linear (E)-homoallyl bromides.The latter were used, in turn, as key intermediates in concise syntheses of thirteen terminally functionalized straight-chain oligoolefins which are known to constitute acetogenin pheromonal components for more than 65 species of lepidopteran insects.

Kolbe electrosynthesis of (E)-11-tetradecenal-The sex pheromone of eastern spruce budworm (Choristoneura of fumiferana)

The synthesis of (E)-11-tetradecenal (7), a potent lepidoptera sex pheromone is reported employing the modified Knoevenagel condensation and Kolbe electrolysis in the key steps.

Synthesis of E,Z-11-tetradecen-1-al

The present invention pertains to a process for making a E,Z-11-tetradecen-1-al containing from 80 to 83 mole percent of the E isomer and from 17 to 20 mole percent of the Z isomer which exhibits pheromone-like activity for the spruce bud worm (choristoneura fumiferana).

Pheromones via Organoboranes. 2. Vinylic Organoboranes. 8. Applications of the General Stereoselective Synthesis of (E)-Disubstituted Alkenes via Thexylchloroborane-Dimethyl Sulfide to the Synthesis of Pheromones Containing an (E)-Alkene Moiety

Various (E)-pheromones of the general structure (E)-X-alken-1-yl acetates, (E)-X-alken-1-ols, and (E)-X-alken-1-als have been prepared via thexylchloroborane-dimethyl sulfide (ThxBHCl*SMe2).Hydroboration of acetate-functionalized alkenes with ThxBHCl*SMe2 gives cleanly the corresponding thexylalkylchloroboranes (ThxBRCl, B).Hydridation of B with potassium triisopropoxyhydride (KIPBH) at -78 deg C gives cleanly the corresponding thexylalkylboranes (ThxBRH, C).These are quenched immediately with 1-halo-1-alkynes to give B-(cis-1-halo-1-alkenyl)thexylalkylboranes (D).Treatment of D with sodium methoxide results in the displacement of bromine by the alkyl group on boron to produce B-(trans-1-alkyl-1-alkenyl)thexylborinates (E).Protonolysis of E with acetic acid provides (E)-X-alken-1-yl acetates in high yields and in >99percent isomeric purities.Treatment of (E)-X-alken-1-yl acetates with base affords the corresponding (E)-X-alken-1-ols.Oxidation of (E)-X-alken-1-ols with dimethyl sulfoxide activated by oxalyl chloride or the complex of dimethyl sulfide and chlorine produces (E)-X-alken-1-als quantitatively.By properly choosing the starting functionalized alkenes and 1-halo-1-alkynes, various (E)-pheromones can be prepared easily.The present procedure appears to be general.There does not appear to be any limitation on the length of the carbon chain or the position of the double bond in the target molecules.