20711-10-8

Basic information

• Product Name: (Z)-11-TETRADECEN-1-YL ACETATE
• Synonyms: acetate,(z)-11-tetradecen-1-o;cis-11-Tetradecen-1-ol acetate;cis-11-Tetradecen-1-yl acetate;cis-11-tetradecen-1-ylacetate;cis-11-tetradecenyl;Z-11-Tetradecenol acetate;(Z)-11-TETRADECEN-1-YL ACETATE;(Z)-tetradec-11-enyl acetate
• CAS NO: 20711-10-8
• Molecular Formula: C₁₆H₃₀O₂
• Molecular Weight: 254.41
• EINECS: 243-982-8
• Mol File: 20711-10-8.mol

Chemical Properties

• Melting Point: <25℃
• Boiling Point: 316.2±11.0℃ (760 torr)
• Flash Point: 87.2±17.6℃
• Appearance: /
• Density: 0.878±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.000416mmHg at 25°C
• Refractive Index: 1.4515 (20℃)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol (Sparingly)
• CAS DataBase Reference: (Z)-11-TETRADECEN-1-YL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-11-TETRADECEN-1-YL ACETATE(20711-10-8)
• EPA Substance Registry System: (Z)-11-TETRADECEN-1-YL ACETATE(20711-10-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 20711-10-8(Hazardous Substances Data)

Usage

Uses

Used in Pest Control:
(Z)-11-TETRADECEN-1-YL ACETATE is used as a pheromone-based pest control agent for managing insect populations, particularly in agricultural settings. It is employed to attract and trap male insects, thereby disrupting their mating patterns and reducing the overall population of pests.
Used in Research:
(Z)-11-TETRADECEN-1-YL ACETATE is also used in research settings to study the mating behavior and communication mechanisms of various insect species. This knowledge can be applied to develop more effective pest control strategies and better understand the biology and ecology of these insects.
Used in Environmental Monitoring:
(Z)-11-TETRADECEN-1-YL ACETATE can be utilized in environmental monitoring programs to detect the presence of specific insect species and assess their population levels. This information can be valuable for predicting potential pest outbreaks and implementing timely control measures.

InChI:InChI=1/C16H30O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h4-5H,3,6-15H2,1-2H3/b5-4-

Upstream product

• 57584-82-4 11-Oxoundecyl acetate 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 33189-72-9 (E)-tetradec-11-en-1-yl acetate 
• 33925-72-3 11-tetradecyne-1-yl acetate 
• 127-09-3 sodium acetate 
• 133074-64-3 Z/E-11-tetradecenyl bromide 
• 34010-15-6 cis-11-tetradecen-1-ol 
• 108-24-7 acetic anhydride 
• 925-90-6 ethylmagnesium bromide 
• 98752-56-8 (Z)-2-(8-phenylthiododec-11-enyloxy)tetrahydro-2H-pyran 
• 114052-40-3 Δ¹¹-tetradecenol 
• 62466-69-7 5-Bromo-1-(1'-ethoxyethoxy)pentane 
• 110065-87-7 (Z)-9-bromonon-3-ene 
• 119265-29-1 1-(1-ethoxyethoxy)-11Z-tetradecene 

Downstream Products

• 3669-80-5 11-hydroxyundecanoic acid 
• 33189-72-9 (E)-tetradec-11-en-1-yl acetate 

Relevant articles and documents

Behavioral responses of Spodoptera littoralis males to sex pheromone components and virgin females in wind tunnel

The major component of the sex pheromone of female Spodoptera littoralis, (Z,E)-9,11-tetradecadienyl acetate (1), elicited all steps of the male behavioral sequence, i.e., wing fanning and taking flight, oriented upwind flight and arrival to the middle of the tunnel, close approach and contact with the source. The activity was equivalent to that elicited by virgin females. In the range of doses tested, the dosage of 1 had no significant effect on the number of source contacts. Male response was significantly affected by light intensity, being optimum at 3 lux. Activity of the minor components (Z)-9-tetradecenyl acetate (2), (E)-11-tetradecenyl acetate (3), tetradecyl acetate (4), (Z)-11-tetradecenyl acetate (5), and (Z,E)-9,12-tetradecadienyl acetate (6) was significantly lower than that of the major component when assayed individually. In multicomponent blends compound 4 appeared to strongly decrease the number of males arrested at the source, the effect being particularly important when compound 5 was present in the blend. Results of single sensillum experiments confirmed the existence of two main physiologically distinct sensillar types. The most common type of sensilla contained a neuron that responded specifically to compound 1. A second type of sensilla, located laterally on the ventral sensory surface, contained two receptor neurons responding to compound 6 and to (Z)-9-tetradecenol. Among short sensilla, one hair responded to compound 4 and could represent a minor sensillar type. No sensory neuron was found to detect the other minor pheromone compounds 2, 3, and 5,.

A "TUNABLE" STEREOSELECTIVE ALKENE SYNTHESIS BY IODODESILYLATION OF VINYLSILANES

The stereoselectivity of iododesilylation of terminal E-vinylsilanes varies with changing amount of Lewis acid.The use of this "tunable" stereoselective reaction was demonstrated by the syntheses of two insect sex pheromones with defined E/Z isomeric rations.

SYNTHESIS OF PHEROMONE DERIVATIVES VIA Z-SELECTIVE OLEFIN METATHESIS

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES

Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

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.

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).

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.

Concise syntheses of insect pheromones using Z-Selective cross metathesis

Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.

Exo- and endohormones. XXIV. 1 a convenient synthesis of (Z)-11-tetradecen-1-YL acetate, component of lepidoptera insect sex pheromone

A new and practical synthesis of (Z)-11-tetradecene-1-yl acetate was developed using commercially raw material. The synthesis was based on a C 10+C2=C12 and C12+C 2=C14 coupling scheme, starting from 1,10-decane-diol. The route involves, as the key step, the use of the mercury derivative of the terminal alkyne ω-functionalised as intermediate, which is lithiated and then alkylated. The first coupling reaction took place between monosodium acetylene obtained in situ and 1-tert-butoxy-10-bromo-decane. The second coupling reaction consisted in directly lithiated of di (t-butoxy-dodec-11-yne) mercury and then alkylated with ethyl bromide obtaining 1-tert-butoxy-tetradec- 11-yne. After acetylation and stereoselective reduction in the presence of NiP-2 catalyst of 1-tertbutoxy- tetradec-11-yne gave (Z)-11-tetradecene-1-yl acetate with 99% isomeric purity.

Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates

Compounds of the formula (I) wherein R2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.