69820-27-5

Basic information

• Product Name: cis-13-octadecenol
• Synonyms: cis-13-octadecenol;(13Z)-13-Octadecene-1-ol;(Z)-13-Octadecen-1-ol;(13Z)-13-Octadecen-1-ol;(13Z)-Octadecen-1-ol;13-(Z)-Octadecen-1-ol;13Z-Octadecen-1-ol;cis-13-Octadecen-1-ol
• CAS NO: 69820-27-5
• Molecular Formula: C₁₈H₃₆O
• Molecular Weight: 268.47784
• Product Categories: Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals;insect pheromone
• Mol File: 69820-27-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 334.3oC at 760 mmHg
• Flash Point: 146.8oC
• Appearance: /
• Density: 0.847g/cm3
• Vapor Pressure: 9.1E-06mmHg at 25°C
• Refractive Index: 1.461
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.20±0.10(Predicted)
• CAS DataBase Reference: cis-13-octadecenol(CAS DataBase Reference)
• NIST Chemistry Reference: cis-13-octadecenol(69820-27-5)
• EPA Substance Registry System: cis-13-octadecenol(69820-27-5)

Safety Data

• Hazardous Substances Data: 69820-27-5(Hazardous Substances Data)

Usage

Uses

(Z)-13-Octadecen-1-ol is a compound structurally related to sex pheromone components of clearwing moths Paranthrene tabaniformis (Lepidoptera, Sesiidae).

Definition

ChEBI: A long-chain fatty alcohol that is stearyl alcohol which has been dehydrogenated to introduce a cis double bond between positions 13 and 14.

InChI:InChI=1/C18H36O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h5-6,19H,2-4,7-18H2,1H3/b6-5-

Upstream product

• 112999-97-0 2-[(12-bromododecyl)oxy]tetrahydro-2H-pyran 
• 3344-77-2 12-bromododecanol 
• 5675-51-4 1,12-dodecandiol 
• 108536-01-2 (Z)-8-(tetrahydro-2H-pyran-2-yloxy)oct-4-enyl 4-methylbenzensulfonate 
• 62422-46-2 (Z)-8-<(tetrahydropyran-2-yl)oxy>oct-4-enol 
• 56506-08-2 (Z)-oct-4-ene-1,8-diol 
• 55362-80-6 9-bromononan-1-ol 
• 3937-56-2 1,9-Nonanediol 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 55695-90-4 2-(9-bromononyloxy)tetrahydropyran 
• 83165-98-4 1-tosyloxynon-4Z-ene 
• 59499-28-4 (Z)-4-nonen-1-ol 
• 146176-63-8 (Z)-1-(tetrahydropyran-2-yloxy)-4-nonene 
• 1120-34-9 methyl cis-13-docosenoate 

Downstream Products

• 822-23-1 stearyl acetate 
• 60037-58-3 (Z)-13-octadecen-1-yl acetate 
• 58594-45-9 (Z)-13-octadecenal 

Relevant articles and documents

Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)

Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.

The stereospecific synthesis of the rice leaffolder moth sex pheromone components from 1,5-cyclooctadiene

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Stereospecific syntheses of a few Lepidoptera pheromones containing (Z)-alkene moiety

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