16974-11-1

Basic information

• Product Name: Z-9-DODECEN-1-YL ACETATE
• Synonyms: CIS-9-DODECEN-1-OL ACETATE;Z-9-DODECEN-1-YL ACETATE;(9Z)-9-Dodecenyl acetate;(Z)-9-Dodecen-1-ol acetate;(z)-9-dodecenyl;(z)-9-dodecenylacetate;(z)-acetate-9-dodecen-1-ol;9-Dodecen-1-ol, acetate, (Z)-
• CAS NO: 16974-11-1
• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.36
• EINECS: 241-054-7
• Product Categories: insect pheromone
• Mol File: 16974-11-1.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 300.1±21.0℃ (760 Torr)
• Flash Point: 96.5±20.4℃
• Appearance: /
• Density: 0.881±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00114mmHg at 25°C
• Refractive Index: 1.4439 (22℃)
• CAS DataBase Reference: Z-9-DODECEN-1-YL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: Z-9-DODECEN-1-YL ACETATE(16974-11-1)
• EPA Substance Registry System: Z-9-DODECEN-1-YL ACETATE(16974-11-1)

Safety Data

• Hazardous Substances Data: 16974-11-1(Hazardous Substances Data)

Usage

Uses

(9Z)-Dodecen-1-ol Acetate is derived from 2-Decyn-1-ol (D228475), which is used in the synthesis of antitumor agents, isomers of Panaxytriol and Falcarinol (F101100). Also used in the synthesis of aromatase inhibitors used in the treatment of cancers, primarily breast and ovarian.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 1433, 1980 DOI: 10.1016/S0040-4039(00)92738-2

InChI:InChI=1/C14H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h4-5H,3,6-13H2,1-2H3/b5-4-

Upstream product

• 29541-97-7 9-acetoxynonal 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 91856-11-0 Δ⁹-dodecen-1-ol 
• 108-24-7 acetic anhydride 
• 35148-18-6 (Z)-9-dodecenol 
• 21676-03-9 (Z)-3-hexenyl iodide 
• 1779-13-1 octadeca-9Z-ene 
• 872-05-9 1-Decene 
• 7642-09-3 cis-3-hexene 
• 14850-22-7 cis-3-octene 
• 693-80-1 oleyl acetate 
• 50816-18-7 9-decen-1-yl acetate 
• 112-62-9 Methyl oleate 
• 143-28-2 oleoyl alcohol 

Downstream Products

• 56219-03-5 (Z)-9-Dodecenal 
• 29541-97-7 9-acetoxynonal 

Relevant articles and documents

Simple stereospecific synthesis of the insect sex pheromones of Cossus cossus, Eupoecilia ambiguella and Orgyia pseudotsugata

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Method for synthesizing grassland spodoptera litura sex pheromone active ingredients

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.

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.