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Linolenic acid

Product Number L 2376

Storage Temperature -0 °C

Replacement for Product Code 85,601-0

Product Description

Molecular Formula: C18H30O2

Molecular Weight: 278.4

CAS Number: 463-40-1

Melting Point: -10.6 °C1

Boiling Point: 230-232 °C (1 mm Hg)

Synonym: á-linolenic acid.

Linolenic acid is a component of some plant seed oils.2

Plant derived oils such as linseed oil are a source for

its isolation.3 Linolenic acid is an essential fatty acid.3

Polyunsaturated fatty acids (such as linolenic acid)

autooxidize by three competing pathways.6 After

formation of a peroxy radical, the following can occur:

1) abstraction of hydrogen atoms to give

hydroperoxide products,

2) beta-scission of the carbon-oxygen bond to give

back carbon radicals, including isomerized carbon

radicals,

3) cyclizing to give a cyclic peroxy radical.

A procedure for determination of the amount of

oxidation in a lipid by way of the oxidation index has

been published.4 The oxidation index is a ratio of the

absorbance at 233 nm to the absorbance at 215 nm.

The latter wavelength was chosen since there is little

contribution of the fatty acid carbonyl to the

absorbance at this wavelength, thus allowing Beers

Law to be followed.

Lipid oxidation, mechanisms, products and biological

significance for fatty acids, including linolenic acid and

oleic acid has been discussed.5,7

Precautions and Disclaimer

For Laboratory Use Only. Not for drug, household or

other uses.

Preparation Instructions

Linolenic acid is not soluble in water. It is soluble in

ethanol, ether, and chloroform.8

References

1. Holman, R. T., and Elmer, O. C., The Rates Of

Oxidation Of Unsaturated Fatty Acids And Esters.

J. Am. Oil Chem. Soc., 24, 127-129 (1947).

2. Oil Crops of the World, Robbelen, G., et al., eds.,

McGraw-Hill (New York, NY: 1989), pp. 66-67.

3. The Merck Index, 12th ed., Entry# 5530.

4. Klein, R. A., The Detection Of Oxidation In

Liposome Preparations. Biochim. Biophys. Acta.,

210(3), 486-489 (1970).

5. Frankel, E. N., Lipid Oxidation: Mechanisms,

Products and Biological Significance. J. Am. Oil

Chem. Soc., 61(12), 1908-1916 (1984).

6. Fox, J., Fatty Acids Spontaneous Oxidation

Clarified. Chemical and Engineering News, Oct.

26, 18-19 (1981).

7. Kim, R. S., and LaBella, F. S., Comparison Of

Analytical Methods For Monitoring Autooxidation

Profiles Of Authentic Lipids. J. Lipid Res., 28(9),

1110-1117 (1987).

8. Data for Biochemical Research, 3rd ed., Dawson,

R. M. C., et al., Oxford University Press (New

York, NY: 1986), pp. 176-177.

RLG/RXR 6/03