60037-58-3

Basic information

• Product Name: Z-13-OCTADECEN-1-YL ACETATE
• Synonyms: (z)-11-hexadecenyl;acetate,(z)-13-octadecen-1-o;Z-13-OCTADECEN-1-YL ACETATE;(Z)-13-Octadecen-1-olacetate;(E)-13-Octadecenyl acetate;13Z-18Ac;(13Z)-Octadecenyl acetate;13-(Z)-Octadecenyl acetate
• CAS NO: 60037-58-3
• Molecular Formula: C₂₀H₃₈O₂
• Molecular Weight: 310.51
• Product Categories: insect pheromone
• Mol File: 60037-58-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 379.5±11.0℃ (760 Torr)
• Flash Point: 87.8±17.6℃
• Appearance: /
• Density: 0.872±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.82E-06mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: Z-13-OCTADECEN-1-YL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: Z-13-OCTADECEN-1-YL ACETATE(60037-58-3)
• EPA Substance Registry System: Z-13-OCTADECEN-1-YL ACETATE(60037-58-3)

Safety Data

• Hazardous Substances Data: 60037-58-3(Hazardous Substances Data)

Usage

Description

Z-13-OCTADECEN-1-YL ACETATE, also known as (13Z)-Octadecenyl Acetate, is a chemical compound with the molecular formula C20H38O2. It is an acetate derivative of an octadecenyl group, which is a long-chain hydrocarbon with a double bond at the 13th carbon. Z-13-OCTADECEN-1-YL ACETATE is known for its specific chemical properties and potential applications in various fields.

Uses

Used in Chemical Synthesis:
Z-13-OCTADECEN-1-YL ACETATE is used as a synthetic intermediate for the stereoselective synthesis of Cnaphalocrocis sex pheromone components from cyclooctadiene. This application is particularly relevant in the field of chemical ecology, where the synthesis of pheromones is crucial for understanding and manipulating insect behavior.

InChI:InChI=1/C20H38O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-20(2)21/h6-7H,3-5,8-19H2,1-2H3/b7-6-

Synthetic route

(Z)-octadec-13-en-1-ol (69820-27-5) + acetic anhydride (108-24-7) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
With pyridine for 24h; Ambient temperature;	100%
With pyridine at 0℃; for 3h;	96%
With pyridine In dichloromethane for 5h; Ambient temperature;	86%

cis-13-docosenoic acid (112-86-7) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: 91 percent / 30percent H2O2, HCOOH 2: 89 percent / aq. Na2CO3, H3PO4, NaIO4 3: 1.) NaH, DMSO 4: PTS 5: 90 percent / LiAlH4 (LAH) / diethyl ether 6: 100 percent / pyridine / 24 h / Ambient temperature View Scheme

13,14-dihydroxy-behenic acid (616-01-3) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 89 percent / aq. Na2CO3, H3PO4, NaIO4 2: 1.) NaH, DMSO 3: PTS 4: 90 percent / LiAlH4 (LAH) / diethyl ether 5: 100 percent / pyridine / 24 h / Ambient temperature View Scheme

13-oxotridecanoic acid (65157-88-2) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) NaH, DMSO 2: PTS 3: 90 percent / LiAlH4 (LAH) / diethyl ether 4: 100 percent / pyridine / 24 h / Ambient temperature View Scheme

(13Z)-octadec-13-enoic acid (693-71-0, 7378-89-4, 13126-39-1) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: PTS 2: 90 percent / LiAlH4 (LAH) / diethyl ether 3: 100 percent / pyridine / 24 h / Ambient temperature View Scheme

cis-13-octadecenoic acid, methyl ester (13058-55-4) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / LiAlH4 (LAH) / diethyl ether 2: 100 percent / pyridine / 24 h / Ambient temperature View Scheme

4-(Z)-nonenemagnesium bromide (82260-32-0, 142524-63-8) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 54 percent / Li2CuCl4 / tetrahydrofuran / 3 h / -10 °C 2: 53 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 55 °C 3: 86 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme

1-tetrahydropyranyloxy-13-(Z)-octadecene (130253-49-5) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 53 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 55 °C 2: 86 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / ethanol / 80 °C 2: pyridine / 3 h / 0 °C View Scheme

(Z)-1-(tetrahydropyran-2-yloxy)-4-nonene (146176-63-8) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridinium p-toluenesulfonate / methanol / 80 °C 2: pyridine 3: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 4: pyridinium p-toluenesulfonate / ethanol / 80 °C 5: pyridine / 3 h / 0 °C View Scheme

(Z)-4-nonen-1-ol (59499-28-4) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine 2: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 3: pyridinium p-toluenesulfonate / ethanol / 80 °C 4: pyridine / 3 h / 0 °C View Scheme

1-tosyloxynon-4Z-ene (83165-98-4) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 2: pyridinium p-toluenesulfonate / ethanol / 80 °C 3: pyridine / 3 h / 0 °C View Scheme

2-(9-bromononyloxy)tetrahydropyran (55695-90-4) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 2: pyridinium p-toluenesulfonate / ethanol / 80 °C 3: pyridine / 3 h / 0 °C View Scheme

1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions

Yield

Multi-step reaction with 9 steps 1: peracetic acid / dichloromethane 2: pyridinium p-toluenesulfonate / tetrahydrofuran 3: pyridine / 4 h / 20 °C 4: dilithium tetrachlorocuprate / tetrahydrofuran / 3 h / -40 °C 5: pyridinium p-toluenesulfonate / methanol / 80 °C 6: pyridine 7: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 8: pyridinium p-toluenesulfonate / ethanol / 80 °C 9: pyridine / 3 h / 0 °C View Scheme

1,9-Nonanediol (3937-56-2) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogen bromide / benzene 2: pyridinium p-toluenesulfonate / dichloromethane 3: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 4: pyridinium p-toluenesulfonate / ethanol / 80 °C 5: pyridine / 3 h / 0 °C View Scheme

9-bromononan-1-ol (55362-80-6) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridinium p-toluenesulfonate / dichloromethane 2: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 3: pyridinium p-toluenesulfonate / ethanol / 80 °C 4: pyridine / 3 h / 0 °C View Scheme

(Z)-oct-4-ene-1,8-diol (56506-08-2, 62422-45-1) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 8 steps 1: pyridinium p-toluenesulfonate / tetrahydrofuran 2: pyridine / 4 h / 20 °C 3: dilithium tetrachlorocuprate / tetrahydrofuran / 3 h / -40 °C 4: pyridinium p-toluenesulfonate / methanol / 80 °C 5: pyridine 6: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 7: pyridinium p-toluenesulfonate / ethanol / 80 °C 8: pyridine / 3 h / 0 °C View Scheme

(Z)-8-<(tetrahydropyran-2-yl)oxy>oct-4-enol (62422-46-2) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 7 steps 1: pyridine / 4 h / 20 °C 2: dilithium tetrachlorocuprate / tetrahydrofuran / 3 h / -40 °C 3: pyridinium p-toluenesulfonate / methanol / 80 °C 4: pyridine 5: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 6: pyridinium p-toluenesulfonate / ethanol / 80 °C 7: pyridine / 3 h / 0 °C View Scheme

(Z)-8-(tetrahydro-2H-pyran-2-yloxy)oct-4-enyl 4-methylbenzensulfonate (108536-01-2) → (Z)-13-octadecen-1-yl acetate (60037-58-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: dilithium tetrachlorocuprate / tetrahydrofuran / 3 h / -40 °C 2: pyridinium p-toluenesulfonate / methanol / 80 °C 3: pyridine 4: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 5: pyridinium p-toluenesulfonate / ethanol / 80 °C 6: pyridine / 3 h / 0 °C View Scheme

Upstream product

• 69820-27-5 (Z)-octadec-13-en-1-ol 
• 108-24-7 acetic anhydride 
• 112-86-7 cis-13-docosenoic acid 
• 616-01-3 13,14-dihydroxy-behenic acid 
• 65157-88-2 13-oxotridecanoic acid 
• 693-71-0 (13Z)-octadec-13-enoic acid 
• 13058-55-4 cis-13-octadecenoic acid, methyl ester 
• 82260-32-0 4-(Z)-nonenemagnesium bromide 
• 130253-49-5 1-tetrahydropyranyloxy-13-(Z)-octadecene 
• 146176-63-8 (Z)-1-(tetrahydropyran-2-yloxy)-4-nonene 
• 59499-28-4 (Z)-4-nonen-1-ol 
• 83165-98-4 1-tosyloxynon-4Z-ene 
• 55695-90-4 2-(9-bromononyloxy)tetrahydropyran 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 

Relevant articles and documents

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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