Linoleoyl Chloride Chemical Properties

Boiling point:

150-152 °C (0.5 mmHg)

Density 

0.93

refractive index 

1.47-1.49

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

clear liquid

color 

Colorless to Light orange to Yellow

Stability:

Moisture Sensitive

EPA Substance Registry System

9,12-Octadecadienoyl chloride, (9Z,12Z)- (7459-33-8)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

28A-26-45-36/37/39-27

RIDADR 

UN 3265 8/PG 2

TSCA 

TSCA listed

HazardClass 

8

PackingGroup 

II

HS Code 

29130000

MSDS

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Linoleoyl Chloride Usage And Synthesis

Chemical Properties

dark brown liquid or oil

Uses

Linoleoyl chloride is a volatile compound found in the leaves of white cedar. It is used in the production of antimicrobial agents.

Preparation

A solution of linoleoyl chloride prepared from linoleic acid (2 mmol) and oxalyl chloride (3 mmol) in dichloromethane (5 mL), as described above, was added dropwise to a stirred solution of 3 (1 mmol) in pyridine (5 mL) at room temperature. The reaction mixture was stirred for 1 h at room temperature and then processed as already described. The crude product was subjected to SiO₂ column chromatography by elution with n-hexane/ethyl acetate (20:1, vol/vol) to yield OLP (6) as a colorless oil (0.70 g, 82%). ¹H NMR (CDCl₃, δ): 0.86–0.90 (m by three overlapping triplets, 9H, –CH₃), 1.25–1.62 (m, 64H, –CH₂–), 2.01–2.07 (m, 8H, –C=C–CH₂–), 2.31 (t, J = 6.4 Hz, 6H, –OCO–CH₂–), 2.77 (t, J = 5.5 Hz, 2H, –C=C–CH₂–C=C–), 4.14 (dd, J = 12.2 and 6.3 Hz, 2H, 1- and 3-H), 4.28 (dd, J = 12.2 and 4.4 Hz, 2H, 1- and 3-H), 5.27 (m, 1H, 2-H), and 5.34 ppm (m, 6H, –CH=CH–). ¹³C NMR (CDCl₃, δ): 62.07 (glyceryl C1 and C3), 68.86 (glyceryl C2), 87.11 (–CH–OOH–), 127.86, 128.05, 129.69, 129.97, 129.99, 130.21 (–C=C–), 172.82, and 173.25 ppm (–COO–).

References

[1] Hui, S.-P., Murai, T., Yoshimura, T., Chiba, H., & Kurosawa, T. (2003). Simple chemical syntheses of TAG monohydroperoxides. Lipids, 38 12, 1287–1292. https://doi.org/10.1007/s11745-003-1191-9
[2] Awl, R. A., Frankel, E. N., & Weisleder, D. (1989). Synthesis and characterization of triacylglycerols containing linoleate and linolenate†. Lipids, 24 10, 866–872. https://doi.org/10.1007/BF02535761

Linoleoyl Chloride (7459-33-8)Related Product Information

• TRANS-1,3-DIPHENYL-2-PROPEN-1-OL
• Linoleoyl Chloride
• Octanoyl chloride
• Heptanoyl chloride
• NONANOYL CHLORIDE