42521-46-0

Basic information

• Product Name: (9Z,12E)-9,12-Tetradecadien-1-ol
• Synonyms: (9Z,12E)-Tetradecadien-1-ol;(9Z,12E)-9,12-Tetradecadien-1-ol
• CAS NO: 42521-46-0
• Molecular Formula: C₁₄H₂₆O
• Molecular Weight: 210.36
• Mol File: 42521-46-0.mol

Chemical Properties

• Boiling Point: 98-99 °C(Press: 0.1 Torr)
• Appearance: /
• Density: 0.860±0.06 g/cm3(Predicted)
• PKA: 15.20±0.10(Predicted)
• CAS DataBase Reference: (9Z,12E)-9,12-Tetradecadien-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (9Z,12E)-9,12-Tetradecadien-1-ol(42521-46-0)
• EPA Substance Registry System: (9Z,12E)-9,12-Tetradecadien-1-ol(42521-46-0)

Safety Data

• Hazardous Substances Data: 42521-46-0(Hazardous Substances Data)

Usage

Uses

Used in Biological Studies:
(9Z,12E)-9,12-Tetradecadien-1-ol is used as a key compound in the biological study of sequence, identification, and functional characterization of sex pheromone receptors in beet armyworms. Its role in these studies is crucial for understanding the chemical communication and mating behavior of these insects, which can have significant implications for pest management and agricultural practices.
Used in Chemical Research:
(9Z,12E)-9,12-Tetradecadien-1-ol can also be utilized in chemical research as a starting material or intermediate for the synthesis of various complex organic molecules. Its unique structure and functional groups make it a valuable building block for the development of new compounds with potential applications in pharmaceuticals, agrochemicals, and other industries.
Used in Pheromone Production:
In the field of chemical ecology, (9Z,12E)-9,12-Tetradecadien-1-ol can be employed in the production of pheromones, which are chemical signals used by animals for communication. (9Z,12E)-9,12-Tetradecadien-1-ol's ability to mimic or interact with sex pheromone receptors in specific insect species can be harnessed for the development of pheromone-based pest control strategies, reducing the reliance on chemical pesticides and promoting more sustainable agricultural practices.
Used in Fragrance Industry:
Due to its unique chemical structure and properties, (9Z,12E)-9,12-Tetradecadien-1-ol can be used as a component in the fragrance industry. It can contribute to the development of new and innovative scents, adding complexity and depth to perfumes, colognes, and other fragrance products.

Upstream product

• 30507-70-1 Tetradec-9Z,12E-dien-1-yl Acetate 
• 53143-98-9 (9Z,12E)-9,12-Tetradecadiensaeure-methylester 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 112464-06-9 1-<(tetrahydro-2H-pyran-2-yl)oxy> 9Z, 12E-tetradecadiene 
• 143-28-2 oleoyl alcohol 
• 7319-00-8 (E)-1,4-hexadiene 
• 68516-29-0 1-(Tetrahydropyran-2-yloxy)tetradec-12E-en-9-yne 
• 629-41-4 1,8-Octanediol 
• 53143-96-7 <(E)-3-Pentenyl>triphenylphosphonium-bromid 
• 70654-41-0 [1-(8-tetrahydropyran-2-yloxy-octyl)-hexa-2t,4t-dienyl]-phosphonic acid diethyl ester 
• 120593-09-1 ((E)-Pent-3-enylidene)-triphenyl-λ⁵-phosphane 
• 81651-56-1 2-[((9E,12E)-Tetradeca-9,12-dienyl)oxy]-tetrahydro-pyran 
• 63072-78-6 sorbyl bromide 
• 70654-44-3 (Z,E)-9,12-tetradecadien-1-ol 

Downstream Products

• 30507-70-1 Tetradec-9Z,12E-dien-1-yl Acetate 
• 58257-52-6 (Z)-undec-9-en-1-ol 
• 87092-33-9 (Z,E)-9,12-tetradecadienal 
• 51354-22-4 (Z,Z)-9,12-tetradecadienyl acetate 

Relevant articles and documents

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.

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.

Facile synthesis of mill moth's sex pheromone components

An improved method for the preparation of mill moth's sex pheromone components in high diastereomeric purity is described. Copyright Taylor & Francis Group, LLC.

Stereodirectional synthesis of the main component of pheromone (9Z,12E)-tetradeca-9,12-dienyl acetate by cross-coupling

By cross-coupling of alkynyl cuprate with crotyl halides was synthesized (9Z,12E)-tetradeca-9-12-dienyl acetate, the main component of pheromones of several insect species Lepidoptera. The assignment of the chemical shifts of diene system was performed by 1H and 13NMR spectroscopy.

SYNTHESIS OF THE SEX PHEROMONE OF THE GRAIN MOTH Ephestia Elutella

A most convenient synthesis of tetradeca-9Z,12E-dien-1-ol and its acetate - components of the sex pheromone of the grain moth - has been carried out on the basis of a scheme for obtaining a cis-1,trans-4-dienic system.

SYNTHESES WITH SULFONES XLVII : STEREOSELECTIVE ACCESS TO 1,3- AND 1,4-DIENES THROUGH HYDROGENOLYSIS OF BENZENESULFONYLDIENES. APPLICATION TO PHEROMONE SYNTHESIS.

The stereospecific reduction of EE 2-benzenesulfonyl-1,3-dienes to ZE 1,3-dienes with Grignard reagents under transition metal catalysis is described.Hydrogenolysis of the sulfonyl moiety of 2-benzenesulfonyl-1,4-dienes to ZE 1,4-dienes with sodium dithionite is reported.These techniques have been applied to the stereoselective synthesis of (7E, 9Z) dodecadienyl acetate 3d, (9Z, 11E) tetradecadienyl acetate 3e and (9Z, 12E) tetradecadienyl acetate, 6b.

Pheromones, XXXV. - Stereoselective Syntheses of 1,4-Alkadienes

The stereoselective synthesis of 1,4-alkadienes via Julia synthesis, Wittig reaction, Crombie synthesis and methylene interruption of conjugated alkadienylphosphonates is described.