71317-73-2

Basic information

• Product Name: 11,13-Hexadecadienal,(11Z,13Z)-
• Synonyms: 11,13-Hexadecadienal,(11Z,13Z)-;Nowtechnicalpheromone;(11Z,13Z)-11,13-Hexadecadienal;(Z,Z)-11,13-Hexadecadienal;11,13-Hexadecadienal, (Z,Z)-;Epa pesticide chemical code 000711;7Z11Z13E-16CHO
• CAS NO: 71317-73-2
• Molecular Formula: C₁₆H₂₈O
• Molecular Weight: 236.39292
• Mol File: 71317-73-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 332.7°C at 760 mmHg
• Flash Point: 162.8°C
• Appearance: /
• Density: 0.852±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.000143mmHg at 25°C
• Refractive Index: 1.4768 (589.3 nm 26℃)
• CAS DataBase Reference: 11,13-Hexadecadienal,(11Z,13Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 11,13-Hexadecadienal,(11Z,13Z)-(71317-73-2)
• EPA Substance Registry System: 11,13-Hexadecadienal,(11Z,13Z)-(71317-73-2)

Safety Data

• Hazardous Substances Data: 71317-73-2(Hazardous Substances Data)

Usage

General Description

11,13-Hexadecadienal, (11Z,13Z)- is a chemical compound that belongs to the class of compounds known as alpha, beta-unsaturated aldehydes. It is a long-chain aldehyde with a 16-carbon chain and two conjugated double bonds at the 11th and 13th positions. 11,13-Hexadecadienal,(11Z,13Z)- is found in various natural sources, including fruits, vegetables, and essential oils, and it contributes to their characteristic flavor and aroma. It is also used in the production of perfumes and flavorings. Additionally, 11,13-Hexadecadienal, (11Z,13Z)- has been identified as a potential attractant for certain pest insects and is being studied for its potential use in pest management strategies.

InChI:InChI=1/C16H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h3-6,16H,2,7-15H2,1H3/b4-3-,6-5-

Upstream product

• 1214742-94-5 (Z)-1,1-diethoxyhexadec-13-en-11-yne 
• 1568-65-6 bis(cyclohexanyl)borane 
• 71084-07-6 1-tetrahydropyranyloxy 11-dodecyne 
• 71673-23-9 (11Z,13Z)-1,1-diethoxy-11,13-hexadecadiene 
• 71720-83-7 (Z,Z)11,13-hexadecadien, 1-ol 
• 53463-68-6 1-bromo-10-decanol 
• 1214742-93-4 11-dodecynal diethyl acetal 
• 71673-31-9 1,1-diethoxy-11,13-hexadecadiyne 
• 85416-30-4 (Z)-12-Iodo-1-(2-tetrahydropyranyloxy)-11-dodecene 
• 85416-27-9 12-Iodo-1-(2-tetrahydropyranyloxy)-11-dodecyne 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 84433-06-7 (Z)-12-pentadecen-10-ynyl chloride 
• 84433-05-6 14-Chloro-1-tetradecen-4-yn-3-ol Acetate 
• 71317-67-4 15-Chloro-(Z,Z)-3,5-pentadecadiene 

Downstream Products

• 71720-83-7 (Z,Z)11,13-hexadecadien, 1-ol 
• 73264-91-2 (11E,13E)-11,13-hexadecadienal 

Relevant articles and documents

Facile and efficient syntheses of (11Z,13Z)-hexadecadienal and its derivatives: Key sex pheromone and attractant components of notodontidae

Syntheses of (11Z,13Z)-hexadecadienal (1), (11Z,13Z)-hexadecadienol (2), (11Z,13Z)-hexadecadien-1-yl acetate (3), and (Z)-13-hexadecen-11-ynal (4) from commercially available starting material 10-bromo-1-decanol are reported. These (Z,Z)-dienes and conjugated en-yne moieties are common in sex pheromone and attractant components for many Notodontide insect pests. The synthetic scheme, using the C10 + C3 + C3 strategy, was mainly based on three key steps: Alkylation of lithium alkyne under a low temperature, cis-Wittig olefination of the aldehyde with propylidentriphenylphosphorane, and hydroboration-protonolysis of alkyne. This synthetic route provided (11Z,13Z)-hexadecadienal (1) in a 23.0% total yield via an eight-step sequence, alcohol (2) in a 21.9% total yield, acetate (3) in a 21.4% total yield, and (Z)-13-hexadecen-11-ynal (4) in a 34.7% total yield. This simple strategy provides a new way to achieve syntheses of the key sex pheromones of Notodontide insect pests.

SYNTHETIC NAVEL ORANGEWORM PHEROMONE COMPOSITION AND METHODS RELATING TO PRODUCTION OF SAME

One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.

Synthetic pheromone compositions

The present invention provides compounds useful for preparing synthetic pheromone compositions that can be used as attractants or inhibitors of insect species. The compositions are useful in the control of navel orangeworm or meal moth insect pests.