67818-23-9

Usage

Uses

Used in Perfumery and Fragrance Industry:
(7Z,9Z)-7,9-Dodecadien-1-ol acetate is used as a scent enhancer for its sweet, floral, and fruity odor, adding depth and complexity to perfumes and fragrances. Its natural occurrence in fruits and flowers makes it a desirable component in the creation of authentic and long-lasting scents.
Used in Flavor Industry:
In the flavor industry, (7Z,9Z)-7,9-Dodecadien-1-ol acetate is utilized as a flavor ingredient in food products. Its unique odor profile contributes to the enhancement of flavors, providing a pleasant and appetizing taste to various consumables.
Used in Industrial and Commercial Applications:
(7Z,9Z)-7,9-Dodecadien-1-ol acetate is also employed in industrial and commercial applications beyond the perfumery and flavor industries. Its versatility as a scent and flavor enhancer makes it suitable for a wide range of products, from cleaning agents to air fresheners, where it can improve the overall sensory experience for consumers.

Upstream product

• 16666-78-7 propylidenetriphenylphosphorane 
• 79837-91-5 9-(Tetrahydro-2-pyranyloxy)-2-noninal 
• 99393-41-6 (Z)-9-Dodecen-7-ynyl acetate 
• 58766-03-3 1-(tetrahydro-2H-pyran-2-yl)oxy-7,9-dodecadiene 
• 108-24-7 acetic anhydride 
• 154556-91-9 (7E,9Z)-dodec-7,9-dien-1-ol 
• 13175-44-5 oct-7-en-1-ol 
• 629-41-4 1,8-Octanediol 
• 14596-92-0 cis-1,3-hexadiene 
• 5048-35-1 oct-7-en-1-yl acetate 
• 94742-72-0 1-iodo-(E)1-octen-8-yl acetate 

Relevant academic research and scientific papers

METHOD FOR PRODUCING COMPOUND HAVING CONJUGATED DIENE STRUCTURE

PROBLEM TO BE SOLVED: To provide a method capable of industrially producing a conjugated diene or a conjugated triene in a short process from a raw material which is easy to obtain and handle. SOLUTION: A conjugated diene is produced from a 3-alkenal via reactions of the following first step, second step, and third step in this order: the first step of reacting a Grignard reagent with the 3-alkenal to obtain a homoallylic alcohol; a second step of reacting an esterification reagent or a halogenation reagent with the homoallylic alcohol to obtain a sulfonic ester or a halogenated product; and a third step of having a base act on the sulfinic acid ester or the halogenated product to cause an elimination reaction. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS

Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.

Synthesis and field evaluation of synthetic blends of the sex pheromone of crocidosema aporema (lepidoptera: Tortricidae) in soybean

Crocidosema (= Epinotia) aporema (Walsingham) (Lepidoptera: Tortricidae) is a bud borer that feeds on soybean and forage legumes. Its economic importance is restricted to South America, where it can alternate throughout the year between forage and grain legumes. The sex pheromone of C. aporema females is composed of a 15:1 mixture of (7Z,9Z)-dodeca-7,9-dien-1-ol and (7Z,9Z)- dodeca-7,9-dienyl acetate. Aiming at the development of a monitoring tool, it was synthesized both components of the pheromone and evaluated male captures in pheromone traps baited with different blends of synthetic pheromone, in an experimental soybean field in Uruguay. The conjugated dienes were obtained from 2-pentyn-1-ol and 1,7-heptanediol, by oxidation of the former, Wittig coupling and Zn-catalyzed reduction of the triple bond. The 1:1 mixture was the most efficient in capturing males. The pheromone traps were attractive for up to 40 days, even with small septum loads (0.1 mg) and low population levels.

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.

Synthesis of (7Z,9Z)-dodecadienyl acetate, a component of sex pheromones of the leafrollers Epinotia and Eucosma, using conjugated diynols

Two analogous routes to the title pheromones were elaborated based on organocuprate cross-coupling of Z,Z-dienic electrophiles, (2Z,4Z)-1-acetoxy-2,4-heptadiene (6) and (3Z,5Z)-1-bromoctadiene (8), with ω-tert-butoxy-1-chloropentane and -butane, respectively.Optimal conditions for the reaction of 2,4-heptadiyn-1-ol and 3,5-octadiyn-1-ol to the respective Z,Z-alkadienols as precursors for the electrophiles were found.Treatment of diynols with activated zinc in aqueous alcohol provided high geometrical purity of the product (> 94percent).In both cases, copper-catalyzed cross-coupling afforded 1-tert-butoxy-7,9-dodecadiene (four stereoisomers), acetolysis of which gave the target pheromone contaminated by stereoisomers.In the case of allylic electrophile 6, the reaction occured with the loss of the initial configurational purity, whereas the use of homoyllylic bromide 8 ensured almost complete retention of the configuration of the double bonds and obtaining the target pheromone of 87percent configurational purity.

GENERAL METHODOLOGY FOR THE SYNTHESIS OF CONJUGATED DIENIC INSECT SEX PHEROMONES

A general methodology for the synthesis of various type of dienic insect sex pheromones (Z-E, E-Z, Z-Z) is based on the carbocupration of acetylene by functionalised or non-functionalised lithium dialkyl cuprates, followed by the coupling of the resulting Z dialkenyl cuprates with functionalised or non-functionalised E or Z alkenyl iodides under Pd0 catalysis.The following compounds were efficiently synthesized with a high degree of stereoisomeric purity: (E-Z)7,9-dodecadien,-1-yl acetate 1 (Lobesia botrana), (E-Z)10,12-hexadecadien,-1-ol 2 (Bombyx mori), (Z-E)9,11-tetradecadien,-1-yl acetate 3 (Spodoptera littoralis), (Z-E)5,7 dodecadien-1-ol 4 (Malascoma disstria), (Z-Z)11, 13-Hexadecadien-1-al 5 (Amyelois transitella), (Z)9,11-dodecadien-1-yl acetate 6 (Diparopsis castanea) and (Z-Z)9,11-tridecadien-1-yl acetate 22 (a known "pseudo-pheromone").