63408-45-7

Basic information

• Product Name: (Z)-7-Nonadecen-11-one
• Synonyms: (Z)-12-Nonadecen-9-one;(Z)-7-Nonadecen-11-one;7Z-19-11Kt;cis-12-Nonadecen-9-one
• CAS NO: 63408-45-7
• Molecular Formula: C₁₉H₃₆O
• Molecular Weight: 280.49
• Product Categories: insect pheromone
• Mol File: 63408-45-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 167 °C(Press: 1 Torr)
• Appearance: /
• Density: 0.842±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (Z)-7-Nonadecen-11-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-7-Nonadecen-11-one(63408-45-7)
• EPA Substance Registry System: (Z)-7-Nonadecen-11-one(63408-45-7)

Safety Data

• Hazardous Substances Data: 63408-45-7(Hazardous Substances Data)

Usage

Uses

(12Z)-Nonadecen-9-one can be used in biological study of (Z)-7-Tricosene and monounsaturated ketones as sex pheromone components of the Australian guava moth Coscinoptycha improbana: Identification, field trapping, and phenology.

Upstream product

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• 13423-48-8 triphenylheptylphosphonium bromide 
• 56268-03-2 4-oxo-dodecanal 
• 59724-99-1 bromure d'heptyltriphenylphosphonium 
• 118377-34-7 (11E)-11-(methylthio)-7,11-nonadecadiene 
• 68820-32-6 (Z)-4-undecenal 
• 72855-91-5 (Z)-7-nonadecen-11-ol 
• 629-04-9 1-Bromoheptane 
• 21676-07-3 (Z)-undec-4-en-1-ol 
• 1901-45-7 1-hydroxy-dodecan-4-one 
• 3314-49-6 octyllithium 

Relevant articles and documents

Synthesis and biological testing of ester pheromone analogues for two fruitworm moths (Carposinidae)

A range of ester pheromone analogues for carposinid moths were synthesized and evaluated for biological activity. The analogues aimed to take advantage of the structural commonality of (7Z)-alken-11-ones found in this family. Analogues were tested on two pest species: Heterocrossa rubophaga and Coscinoptycha improbana. Two of the analogues, (2Z)-nonenyl nonanoate and (4Z)-heptyl undecenoate, elicited significant electroantennogram responses. Only (4Z)-heptyl undecenoate gave consistent responses with both moth species in single sensillum recording. Field trapping trials were conducted with these two analogues both individually and in combination with the pheromone of each of the two moth species. No attraction was observed to either of the analogues alone, by either moth species. However, when (4Z)-heptyl undecenoate was coupled with the pheromone, it produced a strong inhibitory effect in H. rubophaga, reducing male moth trap catch by over 95%. No inhibitory effect on male moth trap catch was observed in C. improbana.

Chemistry of Cyclic Phosphorus Compounds. 3. Synthesis of Pheromones Having an γ,δ-Unsaturated Ketone System from 1,1-Diphenylphospholanium Perchlorate

1,1-Diphenylphospholanium perchlorate (1) was converted into the sex pheromones 5a,b of the Japanese female peach fruit moth by use of use tandem Wittig reactions.The ylide of 1 formed with potassium tert-butoxide reacted with heptanal to give Z phosphine oxide 2 with stereoselectivity.The reaction of the anion of 2 with dimethyl disulfide followed by the Horner-Wittig reaction with nonanal or octanal gave the corresponding diene derivatives 4a,b.Hydrolysis of 4a,b afforded the desired the Z γ,δ-unsaturated ketones 5a,b.On the other hand, the conversion of 9, which was derived from methylthio-substituted compound 6, gave an E and Z isomeric mixture of 5b (4:5).

New Synthesis of (Z)-7-Nonadecen-11-one and (Z)-7-Eicosan-11-one: Sex Pheromone Components of Peach Fruit Moth

Reaction of allyl bromide and aldehyde (3) and (4) in the presence of zinc and aqueous ammonium chloride leads to the corresponding homoallylic alcohols (5) and (6) which on hydroboration followed by PCC oxidation give the key intermediates, the ketoaldehydes (9) and (10), respectively in good yields.Ketoaldehydes (9) and (10) on Wittig reaction with heptyltriphenylphosphonium bromide yield the title ketonic pheromones (1) and (2) respectively.