| Identification | Back Directory | [Name]
LINOLEOYL CHLORIDE | [CAS]
7459-33-8 | [Synonyms]
LINOLEOYL CHLORIDE
Linoleoyl Choride
Linoleic acid chloride
Linoleoyl chloride, pract.
(z,z)-12-octadecadienoylchloride
DELTA 9-12 CIS OCTADECADIENOYL CHLORIDE
(9Z,12Z)-octadeca-9,12-dienoyl chloride
9,12-Octadecadienoyl chloride, (9Z,12Z)-
(9Z,12Z)-9,12-Octadecadienoic acid chloride
[(9Z,12Z)-1-Oxo-9,12-octadecadienyl] chloride | [EINECS(EC#)]
231-233-8 | [Molecular Formula]
C18H31ClO | [MDL Number]
MFCD00151403 | [MOL File]
7459-33-8.mol | [Molecular Weight]
298.89 |
| Hazard Information | Back Directory | [Chemical Properties]
dark brown liquid or oil | [Uses]
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 |
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J & K SCIENTIFIC LTD.
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Energy Chemical
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Maya High Purity Chemicals
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