163041-94-9

Basic information

• Product Name: E3,Z8,Z11-Tetradecatriene acetate
• Synonyms: E3,Z8,Z11-Tetradecatriene acetate;3,8,11-Tetradecatrien-1-ol, acetate, (3E,8Z,11Z)- (9CI);Tuta Absoluta PheroMone (Major);E3Z8Z11-14Ac;(3E,8Z,11Z)-3,8,11-Tetradecatrien-1-yl acetate;(3E,8Z,11Z)-Tetradeca-3,8,11-trienyl acetate;(E,Z,Z)-3,8,11-Tetradecatrienyl acetate;Tuta absoluta Pheromone blend
• CAS NO: 163041-94-9
• Molecular Formula: C16H26O2
• Molecular Weight: 250.37644
• Mol File: 163041-94-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 333.6±31.0 °C(Predicted)
• Appearance: /
• Density: 0.903±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: E3,Z8,Z11-Tetradecatriene acetate(CAS DataBase Reference)
• NIST Chemistry Reference: E3,Z8,Z11-Tetradecatriene acetate(163041-94-9)
• EPA Substance Registry System: E3,Z8,Z11-Tetradecatriene acetate(163041-94-9)

Safety Data

• Hazardous Substances Data: 163041-94-9(Hazardous Substances Data)

Usage

Uses

(3E,8Z,11Z)-Tetradeca-3,8,11-trienyl Acetate is a compound found in the pheromones. It is a major sex pheromone component of the tomato pest.

InChI:InChI=1S/C16H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h10-15H,3-9H2,1-2H3

Upstream product

• 824970-38-9 (5Z,8Z)-undeca-5,8-dienal 
• 92845-01-7 allyl acetate 
• 90121-03-2 (3Z,6Z)-1-bromonona-3,6-diene 
• 53046-97-2 (Z,Z)-1-hydroxynona-3,6-diene 
• 92844-99-0 (2E)-5-<(2-tetrahydropyranyl)oxy>pent-2-en-1-ol 
• 51442-80-9 5-(tetrahydro-2H-pyran-2-yloxy)-2-pentyn-1-ol 
• 75-36-5 acetyl chloride 
• 166901-15-1 (E₃,Z₈,Z₁₁)-3,8,11-tetradecatrienyl alcohol 
• 104188-11-6 (4Z,7Z)-4,7-decadien-1-ol 
• 185955-53-7 1-(methoxymethyloxy)pent-4-yne 
• 1455183-94-4 (E₃,Z₈,Z₁₁)-3,8,11-tetradecatrienyl methoxymethyl ether 

Relevant articles and documents

Titanium(II)-based Z-reduction of alkynes: Stereo- and regio-specific Z-dideuteriation of conjugated and methylene-skipped ynes

A TiII-mediated, stereo- and regio-specific reduction of isolated, conjugated and methylene skipped poly-ynes to the corresponding Z-dideuterio polyenes in a one-pot procedure with D2O as deuterium source is described, and this methodology (using H2O) is applied to the synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex attractant of Scrobipalpuloides absoluta, a destructive pest of tomatoes.

Microscale, random reduction: Application to the characterization of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, a new lepidopteran sex pheromone

The major sex attractant released by Scrobipalpuloides absoluta, a devastating tomato pest, was identified as (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate by a novel strategy involving the random reduction of double bonds. The technique is applicable to double bond localization of polyunsaturated compounds available even in nanogram quantities. The triene ester was synthesized by a stereospecific procedure and shown to be highly attractive to conspecific males and identical to the natural substance.

Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones

Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).

5-ACETOXY-(E3)-3-PENTENYL METHOXYMETHYL ETHER AND METHOD FOR PREPARING (E3)-3-ALKENYL ACETATE USING THE SAME

Provided are 5-acetoxy-(E3)-3-pentenyl methoxymethyl ether which can be prepared in conventional reaction equipment and a method for preparing an (E3)-3-alkenyl acetate by using it. More specifically, 5-hydroxy-(E3)-3-pentenyl methoxymethyl ether obtained by reacting 4-formyl-(E3)-3-butenyl methoxymethyl ether with a reductant is reacted with an acetylating agent to prepare 5-acetoxy-(E3)-3-pentenyl methoxymethyl ether. (E3)-3-alkenyl methoxymethyl ether obtained by a coupling reaction between the 5-acetoxy-(E3)-3-pentenyl methoxymethyl ether and a Grignard reagent is treated with an acid, and then reacted with an acetylating agent to prepare the (E3)-3-alkenyl acetate.