54664-97-0

Usage

Uses

Used in Pest Control:
(Z,Z)-tetradeca-9,11-dienyl acetate is used as a pheromone in the pest control industry to control insect populations. By disrupting the mating behavior of insects, it helps in managing and reducing their numbers, making it an effective tool for pest management.
Used in Fragrance and Flavor Industry:
(Z,Z)-tetradeca-9,11-dienyl acetate is used as a key ingredient in the fragrance and flavor industry due to its sweet, floral, and fruity aroma. It is commonly utilized in the formulation of perfumes and aromatherapy products, adding a pleasant and attractive scent to these products.

InChI:InChI=1/C16H28O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h4-7H,3,8-15H2,1-2H3/b5-4-,7-6-

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Relevant academic research and scientific papers

Method for Producing Asymmetric Conjugated Diyne Compound and Method for Producing Z,Z-Conjugated Diene Compound Using the Same

Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z1—Y1 to a coupling reaction with an alkynyl halide (2) Y2—Z2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y2—Z2—C≡C—C≡C—Z1—Y1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

Olefinic acetates, Δ-9,11-14:OAc and Δ-7,9-12:OAc used as sex pheromone components in three geometrid moths, Idaea aversata, I. straminata, and I. biselata (Geometridae, Lepidoptera)

Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C17 to C21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts of Idaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GC-EAD). In extracts of I. straminata, (Z,E)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species, I. biselata, only (Z,Z)-7,9- dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components in I. aversata and I. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings from I. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11- tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also in I. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding the (Z,Z)-7,9- dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed in I. straminata. In field tests, a two-component blend containing (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males of I. aversata. This two-component blend was also attractive to males of I. straminata, but in a ratio of 1:1. High numbers of male I. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components of I. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.

Stereoselective Synthesis of a Potential Sex Pheromone of Stenoma Cecropia (Lepidoptera)

A convenient preparation of (Z,E) 9,11- and (Z,Z) 9,11-tetradecadien-1-yl and (9Z) 9,11-tetradecenyn-1-yl acetate, alcohol and aldehyde with 99.5percent stereoisomeric purity is described.The key step of this synthesis is the carbocupration of acetylene followed by palladium catalyzed cross coupling rection with the appropriate zinc reagent.

SYNTHESIS OF LOBESIA BOTRANA AND SPODOPTERA LITTORALIS NATURAL SEX-ATTRACTANTS

Starting from the coupling reaction of alkyl cuprates with 1-alkynyl-2-propenyl acetates, the title compounds were preparated by short convenient syntheses.