78350-11-5

Basic information

• Product Name: (5Z,7E)-5,7-Dodecadien-1-ol acetate
• Synonyms: (5Z,7E)-5,7-Dodecadien-1-ol acetate
• CAS NO: 78350-11-5
• Molecular Formula: C14H24O2
• Molecular Weight: 224.34
• Mol File: 78350-11-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5Z,7E)-5,7-Dodecadien-1-ol acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z,7E)-5,7-Dodecadien-1-ol acetate(78350-11-5)
• EPA Substance Registry System: (5Z,7E)-5,7-Dodecadien-1-ol acetate(78350-11-5)

Safety Data

• Hazardous Substances Data: 78350-11-5(Hazardous Substances Data)

Usage

Description

(5Z,7E)-5,7-Dodecadien-1-ol acetate is a naturally occurring organic compound that features a unique structure with two double bonds at the 5th and 7th carbon atoms. It is characterized by its distinct chemical properties and is known for its potential applications in various fields.

Uses

Used in Biological Studies:
(5Z,7E)-5,7-Dodecadien-1-ol acetate is used as a chemical marker for the identification of components in the female sex pheromone of the Simao pine caterpillar moth. This application is crucial for understanding the chemical communication and mating behaviors of this species, which can contribute to pest management strategies and ecological research.
Used in Chemical Synthesis:
(5Z,7E)-5,7-Dodecadien-1-ol acetate can be utilized as a starting material or intermediate in the synthesis of various complex organic compounds, including pharmaceuticals, agrochemicals, and fragrances. Its unique structure with double bonds at specific positions makes it a valuable building block for creating novel molecules with potential applications in different industries.
Used in Fragrance Industry:
(5Z,7E)-5,7-Dodecadien-1-ol acetate is used as a fragrance ingredient to create natural and complex scent profiles. Its unique olfactory properties can contribute to the development of new perfumes, colognes, and other scented products, offering a wide range of olfactory experiences for consumers.
Used in Flavor Industry:
(5Z,7E)-5,7-Dodecadien-1-ol acetate can also be employed as a flavoring agent in the food and beverage industry. Its distinct taste and aroma characteristics can be used to enhance or create new flavors in various products, providing a unique sensory experience for consumers.

Upstream product

• 18829-55-5 (E)-2-Heptenal 
• 83085-84-1 <5-(acetyloxy)pentyl>triphenylphosphonium bromide 
• 73416-71-4 (5Z,7E)-5,7-dodecadien-1-ol 
• 108-24-7 acetic anhydride 
• 85838-35-3 (E)-7-dodecen-5-yn-1-yl acetate 
• 75-36-5 acetyl chloride 
• 110-62-3 pentanal 
• 928-90-5 5-hexyl-1-ol 
• 16644-98-7 (E)-1-iodohexene 
• 82751-00-6 (E)-7-dodecen-5-yn-1-ol 
• 693-02-7 hex-1-yne 
• 96754-41-5 7-(2-tetrahydropyranyloxy)-2-heptynal 
• 31608-23-8 7-(tetrahydro-2H-pyran-2-yloxy)hept-2-yn-1-ol 
• 130592-56-2 (2E,4Z)-9-(Tetrahydro-pyran-2-yloxy)-nona-2,4-dien-1-ol 

Downstream Products

• 73416-71-4 (5Z,7E)-5,7-dodecadien-1-ol 
• 75983-34-5 (5Z,7E)-5,7-dodecadienal 

Relevant articles and documents

Synthesis of (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof

The invention belongs to the technical field of insect pheromone synthesis, and discloses a new method for synthesizing (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof.The method takes propynol as an initial raw material to be subjected to coupling with 1-bromobutane to generate 2-heptyne-1-alcohol, triple bond is reduced to be E-type double bond through LiAlH4, 2-heptyne-1-alcohol is oxidized to be olefine aldehyde through PDC, olefine aldehyde reacts with a Wittig reagent (5-ethyoxyl-5-oxopentyl)triphenyl phosphonium bromide to produce (5Z,7E)-dodecane-5,7-dienoic acid ethyl ester which is reduced by LiAlH4 to obtain (5Z,7E)-dodecane-5,7-diene-1-alcohol, (5Z,7E)-dodecane-5,7-diene-1-alcohol reacts with acetyl chloride and propionyl chloride finally to obtain (5Z,7E)-dodecane-5,7-diene-1-alcohol acetate and (5Z,7E)-dodecane-5,7-diene-1-alcohol propionate. The method utilizes LiAlH4 to reduce the triple bond to be the E-type double bond, and utilizes theWittig reaction of the Wittig reagent with the tail end provided with ester group and aldehyde to directly build the Z-type double bond, the synthesis route is simple, convenient and efficient, and the reaction condition is moderate and environmentally friendly.

Stereoselective synthesis of Z, E conjugated dienes: Application to the synthesis of insect sex pheromones

Stereoselective synthesis of insect pheromone components 1-5, p possessing Z,E conjugated diene system has been developed using 1,3-enynes (generated by the in situ alkylation of dianion of prop-2-yn-1-ol followed by Horner-Witting reaction) as precursors.

SYNTHESIS OF INSECT ATTRACTANTS (SEX ATTRACTANTS). VIII. STEREOSELECTIVE SYNTHESIS OF FOUR ISOMERS OF 5,7-DODECADIEN-1-OL AND THEIR ACETATES AND ALDEHYDES, COMPONENTS OF THE SEX PHEROMONES OF INSECTS OF THE Lasiocampidae (Lepidoptera) FAMILY

A new method is proposed for the stereoselective synthesis of four stereoisomers of 5,7-dodecadien-1-ol and their acetates and aldehydes on the basis of the Wittig reaction. 7-(2-Tetrahydropyranyloxy)-2-heptyn-1-ol was obtained by the alkylation of 2-propyn-1-ol with 2-(4-bromobutoxy)tetrahydropyran.By hydrogenation in the presence of colloidal nickel catalyst or by reduction with lithium aluminum hydride it was converted into the Z and E isomers respectively of 7-(2-tetrahydropyranyloxy)-2-hepten-1-ol.Oxidation of the alcohol group in the above-mentioned hydroxy acetals led to the corres ponding aldehydes, which then entered into the Wittig reaction with pentylidenetriphenylphosphorane under the conditions for the formation of a double bond with a specific configuration of the isomers (Z and E).Subsequent removal of the tetrahydropyranyl protection of the alkyl group in the Wittig reaction products gave 5,7-dodecadien-1-ols, which were converted into the corresponding acetates of the aldehydes by acetylation of oxidation.The products are components of the sex pheromones of insects of the Lasiocampidae family.