30562-09-5

Basic information

• Product Name: (Z,E)-9,11-TDDA
• Synonyms: CIS-9, TRANS-11-TETRADECADIENYL ACETATE;(Z,E)-9,11-TDDA;(Z,E)-tetradeca-9,11-dienyl acetate;(9E,11Z)-9,11-Tetradecadien-1-ol acetate;(E,E)-9,11-Tetradecadienyl acetate;9,11-Tetradecadien-1-ol, 1-acetate, (9E,11Z)-;9,11-Tetradecadien-1-ol, acetate, (9E,11Z)-;9,11-Tetradecadien-1-ol, acetate, (Z,E)-
• CAS NO: 30562-09-5
• Molecular Formula: C₁₆H₂₈O₂
• Molecular Weight: 252.39
• EINECS: 250-242-8
• Mol File: 30562-09-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 85-86 °C0.003 mm Hg(lit.)
• Flash Point: 142 °F
• Appearance: /
• Density: 0.89 g/cm³
• Vapor Pressure: 6.47E-06mmHg at 25°C
• Refractive Index: 1.463
• Storage Temp.: −20°C
• CAS DataBase Reference: (Z,E)-9,11-TDDA(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,E)-9,11-TDDA(30562-09-5)
• EPA Substance Registry System: (Z,E)-9,11-TDDA(30562-09-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 30562-09-5(Hazardous Substances Data)

Usage

Description

(Z,E)-9,11-TDDA, also known as (E,E)-9,11-Tetradecadienyl Acetate, is an organic compound with a unique structure consisting of a tetradecadienyl group attached to an acetate group. It is characterized by the presence of two carbon-carbon double bonds in the Z and E configurations, which contribute to its distinct chemical properties and potential applications.

Uses

Used in Agricultural Industry:
(Z,E)-9,11-TDDA is used as an insect control agent for managing various pests that affect crops. Its chemical structure allows it to interfere with the hormonal regulation in insects, disrupting their growth and development, and ultimately leading to their death. This application helps in reducing the reliance on chemical pesticides and promotes sustainable agricultural practices.
Used in Chemical Industry:
(Z,E)-9,11-TDDA is used as a precursor in the preparation of 1,3-dienes through extrusion processes. These 1,3-dienes are valuable intermediates in the synthesis of various chemicals, including pharmaceuticals, polymers, and specialty chemicals. The extrusion process involves heating and forcing the compound through a die, which facilitates the formation of the desired 1,3-diene products. This application highlights the versatility of (Z,E)-9,11-TDDA as a building block in the chemical industry.

InChI:InChI=1/C16H28O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h4-7H,3,8-15H2,1-2H3/b5-4-,7-6+

Upstream product

• 81744-94-7 7-tetrahydropyranyloxy-heptyl-magnesium chloride 
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• 70979-90-7 6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexen-4-yn-3-ol, acetate 
• 76934-45-7 (2E,4Z)-Trideca-2,4-diene-1,13-diol 
• 81744-96-9 cis-tridec-4-en-2-yn-1,13 diol 
• 72553-57-2 (9E,11E)-9,11-Tetradecadienyl-(tetrahydro-2-pyranyl)ether 
• 67886-17-3 7-(tetrahydropyran-2-xyloxy)heptylmagnesium bromide 
• 67818-16-0 (2E,4E)-2,4-Heptadienylacetat 
• 106094-39-7 1-(2-tetrahydropyranyloxy)-(9E,11Z)-9,11-tetradecadiene 
• 106094-32-0 1-(2-tetrahydropyranyloxy)-10-(trimethylsilyl)-(Z)-9-decene 
• 106094-34-2 10-bromo-1-(2-tetrahydropyranyloxy)-(E)-9-decene 
• 106094-31-9 trimethyl-(10-((tetrahydro-2H-pyran-2-yl)oxy)dec-1-yn-1-yl)silane 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 

Relevant articles and documents

Olefinic acetates, Δ-9,11-14:OAc and Δ-7,9-12:OAc used as sex pheromone components in three geometrid moths, Idaea aversata, I. straminata, and I. biselata (Geometridae, Lepidoptera)

Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C17 to C21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts of Idaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GC-EAD). In extracts of I. straminata, (Z,E)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species, I. biselata, only (Z,Z)-7,9- dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components in I. aversata and I. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings from I. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11- tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also in I. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding the (Z,Z)-7,9- dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed in I. straminata. In field tests, a two-component blend containing (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males of I. aversata. This two-component blend was also attractive to males of I. straminata, but in a ratio of 1:1. High numbers of male I. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components of I. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.

A Stereospecific Synthesis of All Four Isomers of 9,11-Tetradecadienyl Acetate Using a General Method Applicable to 1,3-Dienes

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