Skip to main content
SpringerLink
Log in

Hydroxy Radical, Hexanal, and Decadienal Generation by Autocatalysts in Autoxidation of Linoleate Alone and with Eleostearate

  • Original Article
  • Published:
Lipids

Abstract

The formation of hydroxy radicals, hexanal, and 2,4-decadienal was demonstrated from the autocatalytic dimer peroxide which had been reported by us in autoxidizing linoleate (Morita and Tokita in Lipids 41:91–95, 2006). Then, autoxidizing linoleate containing eleostearate was investigated for new autocatalytic substances. The substances obtained were identified as peroxide-linked polymers consisting of both linoleate- and eleostearate-origin units with one hydroperoxy group, and also revealed activity of hydroxy-radical generation. The background of this study is as follows: the above paper reported this autocatalytic dimer peroxide as one of the real radical generators in linoleate autoxidation; this is a peroxide-linked dimer consisting of two linoleate moieties with two hydroperoxy groups, and was much more important than the main-product hydroperoxide in autocatalytic radical supply; its proposed decomposition mechanism has suggested the generation of hydroxy radicals, hexanal, and 2,4-decadienal; on the other hand, analogy to the formation mechanism of this dimer peroxide has predicted the formation of similar polymeric products from conjugated polyene components in lipids. In this study, these two predictions were successfully verified and a discussion is presented in connection with them.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2

Similar content being viewed by others

Abbreviations

AutCat:

Autocatalytic dimer peroxide

MLOOH:

Main-product hydroperoxide of methyl linoleate

oxML:

Autoxidizing methyl linoleate

MLOH:

Hydroxy derivative from the main-product hydroperoxide of methyl linoleate

DNPH:

2,4-Dinitrophenylhydrazone

Azo equiv:

2,2′-Azobis(4-methoxy-2,4-dimethylvaleronitrile) equivalent

References

  1. Morita M, Fujimaki M (1973) Non-hydroperoxy-type peroxides as autocatalysts of lipid autoxidation. Agric Biol Chem 37:1213–1214

    CAS  Google Scholar 

  2. Morita M, Fujimaki M (1973) Minor peroxide components as catalysts and precursors to monocarbonyls in the autoxidation of methyl linoleate. J Agric Food Chem 21:860–863

    Article  CAS  PubMed  Google Scholar 

  3. Morita M, Tanaka M, Takayama Y, Yamamoto Y (1976) Metal-requiring and non-metal-requiring catalysts in the autoxidation of methyl linoleate. J Am Oil Chem Soc 53:487–483

    Article  CAS  Google Scholar 

  4. Morita M, Tokita M (1990) Evaluation of the role of hydroperoxides in the formation of aldehydes during linoleate autoxidation. Chem Phys Lipids 56:209–215

    Article  CAS  Google Scholar 

  5. Morita M, Tokita M (1993) Courses of aldehyde formation during linoleate autoxidation and some information about precursors and mechanism. Chem Phys Lipids 66:13–22

    Article  CAS  Google Scholar 

  6. Morita M, Tokita M (2006) The real radical generator other than main-product hydroperoxide in lipid autoxidation. Lipids 41:91–95

    Article  CAS  PubMed  Google Scholar 

  7. Miyashita K, Fujimoto K, Kaneda T (1984) Structural studies of polar dimers in autoxidizing methyl linoleate during the initial stages of autoxidation. Agric Biol Chem 48:2511–2515

    CAS  Google Scholar 

  8. Miyashita K, Hara N, Fujimoto K, Kaneda T (1985) Dimers formed in oxygenated methyl linoleate hydroperoxides. Lipids 20:578–587

    Article  CAS  Google Scholar 

  9. Hamberg M (1983) Autoxidation of linoleic acid. isolation and structure of four dihydroxyoctadecadienoic acids. Biochim Biophy Acta, Lipids Lipid Metabolism 752:353–356

    Article  CAS  Google Scholar 

  10. Chan H W-S (1987) The mechanism of autoxidation. In: Chan H W-S (ed) Autoxidation of unsaturated lipids. Academic Press, London, pp 10

    Google Scholar 

Download references

Acknowledgments

One of the authors, M. Tokita, carried some of the experiments at Japan Women’s University as a research fellow.

Author information

Authors and Affiliations

  1. Japan Women’s University, Tokyo, Japan

    Makio Morita

  2. Yamawaki Gakuen Junior College, 4-10-36, Akasaka, Minato-ku, Tokyo, 1078371, Japan

    Masako Tokita

Authors
  1. Makio Morita
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Masako Tokita
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Masako Tokita.

About this article

Cite this article

Morita, M., Tokita, M. Hydroxy Radical, Hexanal, and Decadienal Generation by Autocatalysts in Autoxidation of Linoleate Alone and with Eleostearate. Lipids 43, 589–597 (2008). https://doi.org/10.1007/s11745-008-3170-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-008-3170-9

Keywords

Search

Navigation