Fatty acid

DATA No : DFA8060 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-9,12-Dihydroperoxy-10,13,15-Octadecatrienoate

COMMON NAME	:
SYMBOL	:
FORMULA	:	C₁₉H₃₂O₆ MOL.WT (average) : 356.454

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BIOLOGICAL ACTIVITY

It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:	Conjugated diene: lmax=233-235nm(Ref. 8081/8084)

IR SPECTRA	:	OOH group: 3712-3140cm^-¹[bonded], 3530-3510cm^-¹[free]; olefinic protons: 3005cm^-¹; conjugated trans, cis diene: 988-979cm^-¹, 953-935cm^-¹; isolated trans unsaturation: 968-960cm^-¹(Ref. 8081/8084)

NMR SPECTRA	:	¹H-NMR(Ref. 8081/8084): C2: 2.3ppm; C8, 17: 1.8-2.2ppm; C9, 12: 4.40-4.42, 4.86ppm; C10, 11, 13, 14, 15, 16: 5.26-6.28ppm; C18: 1.02ppm; OOH: 8.07ppm

MASS SPECTRA	:	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=453[M-CH3]; 437[M-OCH3]; 378[M-HOTMS]; 311[M-(CH2)7COOCH3]; 221[311-HOTMS]; 157[(CH2)7COOCH3], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(102) m/e=443[M-OCH3]

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

It is produced from a 9-hydroperoxy isomer during autooxidation of linoleate(Ref. 8025/8026/8081). It is produced from 9- or 12-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen (Ref. 8026/8084/8085).

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES

[8025]

AUTHOR	:	Frankel, E. N.
TITLE	:	Volatile lipid oxidation products PubMed ID:6306693
JOURNAL	:	Prog Lipid Res.
VOL	:	22 PAGE : 1-33 (1983)

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[8026]

AUTHOR	:	Frankel, E. N.
TITLE	:	Chemistry of free radical and singlet oxidation of lipids PubMed ID:6100997
JOURNAL	:	Prog Lipid Res.
VOL	:	23 PAGE : 197-221 (1984)

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[8081]

AUTHOR	:	Neff, W. E., Frankel, E. N., and Weisleder, D.
TITLE	:	High Pressure Liquid Chromatography of Autoxidized Lipids: II. Hydroperoxycyclic Peroxides and Other Secondary Products from Methyl Linolenate
JOURNAL	:	Lipids
VOL	:	16 PAGE : 439 -448 (1981)

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[8084]

AUTHOR	:	Neff, W. E., Frankel, E. N., and Weisleder, D.
TITLE	:	Photosensitized Oxidation of Methyl Linolenate. Secondary Products
JOURNAL	:	Lipids
VOL	:	17 PAGE : 780 -790 (1982)

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[8085]

AUTHOR	:	Neff, W. E., and Frankel, E. N.
TITLE	:	Photosensitized Oxidation of Methyl Linolenate Monohydroperoxides: Hydro-Peroxy Cyclic Peroxides, Dihydroperoxides and Hydroperoxy Bis- Cyclic Peroxides
JOURNAL	:	Lipids
VOL	:	19 PAGE : 952 -957 (1984)

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[8096]

AUTHOR	:	Fujimoto, K., Neff, W. E., and Frankel, E. N.
TITLE	:	The reaction of DNA with lipid oxidation products, metals and reducing agents PubMed ID:6466690
JOURNAL	:	Biochim Biophys Acta.
VOL	:	795 PAGE : 100-107 (1984)

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