163041-87-0

Usage

Uses

Used in Pheromone-based Pest Management:
3,8-Tetradecadien-1-ol, acetate, (3E,8Z)(9CI) is used as a sex pheromone for attracting and monitoring the population of S. absoluta moths. This application aids in pest management strategies by enabling farmers and researchers to track and control the spread of these pests, ultimately protecting crops and reducing the need for chemical pesticides.
Used in Chemical Synthesis:
In the chemical industry, 3,8-Tetradecadien-1-ol, acetate, (3E,8Z)(9CI) is used as a reactant in the synthesis of epoxyisoprostanes, which are compounds with anti-inflammatory properties. This application contributes to the development of new pharmaceuticals and therapeutic agents for treating various inflammatory conditions.

Upstream product

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• 172960-51-9 (8Z)-1-(tetrahydropyran-2-yloxy)-8-tetradecen-3-yne 
• 172960-50-8 (E)-1-bromodec-4-ene 
• 150667-91-7 (4E)-1-(Tetrahydropyran-2-yloxy)-4-decene 
• 77022-43-6 4-Decyn-1-yl tetrahydropyranyl ether 
• 10339-62-5 (E)-4-decen-1-ol 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 108-24-7 acetic anhydride 
• 1455184-04-9 (E₃,Z₈)-3,8-tetradecadienyl methoxymethyl ether 
• 501665-82-3 5-hydroxy-(E₃)-3-pentenyl methoxymethyl ether 
• 86197-10-6 4-formyl-(E₃)-3-butenyl methoxymethyl ether 

Relevant academic research and scientific papers

Sex pheromone of tomato pest Scrobipalpuloides absoluta (Lepidoptera: Gelechiidae)

The sex attractant of Scrobipalpuloides absoluta females is a 90:10 mixture of (3E, 8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate. Tetradecadienyl acetates bearing 8Z, 11Z; 3E,8Z; and 3E, 11Z double bonds were synthesized by stereospecific procedures; the mass spectral and gas chromatographic properties of the 3E,8Z isomer were found to be congruent with those of the tetradecadienyl acetate from S. absoluta. In wind tunnel bioassays, a 10:1 mixture of synthetic (3E,8Z, 11Z)-3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate was highly attractive to S. absoluta males. Interestingly, the presence of (8Z.11Z)-8,11-tetradecadien-1-yl acetate (10%) inhibited the response to (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate completely.

Identification of the sex pheromone of Scrobipalpula absolute; determination of double bond positions in triple unsaturated straight chain molecules by means of dimethyl disulphide derivatization

The sex pheromone of Scrobipalpula absoluta (Meyrick) (Lepidoptera: Gelechiidae) was identified as a 92:8 mixture of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate (1) and (3E,8Z)-3,8-tetradecadienyl acetate (2) through mass spectrometric investigation of the dimethyl disulphide derivatives of excised sex pheromone glands. It is the first time that this method was used for triple unsaturated straight chain molecules. Compound (2) was identified as a new pheromone component. A synthetic mixture of the two identified compounds proved to be attractive in wind tunnel experiments.

An Improved and Convenient New Synthesis of the Pheromone Components of the Tomato Leafminer Tuta absoluta

A convenient new synthesis of the two pheromone components of the tomato pest Tuta absoluta in high overall yields and high stereoselectivity (30% yield, E,Z,Z 97% for the major compound and 23% yield, E,Z 99% for the minor component) is reported. The approaches compare favorably with others previously described.

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.

Tetradecatrienyl and tetradecadienyl acetates and their use as sex attractants for tomato pests

The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.