Parinaarihappo

Parinaarihappo
Tunnisteet
CAS-numero	18427-44-6
IUPAC-nimi	(9Z,11E,13E,15Z)-oktadeka-9,11,13,15-tetraeenihappo
SMILES	O=C(O)CCCCCCC/C=C\C=C\C=C\C=C/CC
Ominaisuudet
Kemiallinen kaava	C18H28O2
Moolimassa	276,41372 g/mol
Sulamispiste	85–86 °C
	Infobox OKVirheellinen NIMI-arvo

Parinaarihappo (eng. Parinaric acid) (joko alpha tai beeta) on konjugoitunut monityydyttymätön rasvahappo, jossa on neljä konjugoitunutta kaksoissidosta ja 18 hiiliatomia. Yhdisteen löysivät vuonna 1933 Tsujimoto ja Koyanagi[1]. Yhdistettä on löydetty mm Parinarium laurinum -puun siemenistä, mummonpalsamin (Impatiens balsamina) siemenistä[2] ja korallihaarakkaasta (Clavulina cristata)[3] sekä Sebastiana brasiliensis -tyräkkikasvin siemenistä[4]. Yhdistettä voidaan myös syntetisoida kemiallisesti alfalinoleenihaposta[5]. Parinaarihappoa käytetään lipidi–lipidi-vuorovaikutuksen molekyylitutkimuksessa[6] ja veriseerumin ja veriplasman rasvahappojen konsentraation määrityksessä[7] sekä ruoan proteiinien ja oluen hydrofobisuuden ja vaahtoamisen tutkimuksessa[8][9][10]. Parinaarihapon on myös havaittu tuhoavan leukemiasoluja[11].

Alfa-parinaarihapon CAS-numero on 593-38-4 ja beeta-parinaarihapon CAS-numero on 18841-21-9.

Lähteet

Tsujimoto M, Koyanagi H. (1933). New unsaturated acid in the kernel oil of “akarittom”, “Parinarium laurinum”. I. Kogyo Kagaku Zasshi 36 (Suppl): 110–113.
Gunstone F.D. (1996). Fatty Acid and Lipid Chemistry. Berlin: Springer Verlag, 10. ISBN 0-8342-1342-7.
Endo S, Zhiping G, Takagi T. (1991). Lipid components of seven species of Basidiomycotina and three species of Ascomycotina. Journal of the Japan Oil Chemists' Society 40(7): 574–577.
Spitzer V, Tomberg W, Zucolotto M. (1996). Identification of alpha-parinaric acid in the seed oil of Sebastiana brasiliensis Sprengel (Euphorbiaceae). Journal of the American Oil Chemists' Society 73(5): 569–573.
Kuklev DV, Smith WL: Synthesis of four isomers of parinaric acid. Chem. Phys. Lipids, 2004, 131. vsk, nro 2, s. 215–22.
Conjugated polyene fatty acids as membrane probes: preliminary characterization. Proc. Natl. Acad. Sci. U.S.A., 1975, 72. vsk, nro 5, s. 1649–53.
Berde CB, Kerner JA, Johnson JD. (1980). Use of the conjugated polyene fatty-acid parinaric-acid in assaying fatty-acids in serum or plasma. Clinical Chemistry 26(8): 1173–1177.
Townsend A-A, Nakai S. (1983). Relationships between hydrophobicity and foaming characteristics of food proteins. Journal of Food Science 48(2): 588–594.
Zhu H, Damodaran S. (1994). Heat-induced conformational changes in whey protein isolate and its relation to foaming properties. Journal of Agricultural and Food Chemistry 42(4): 846–855.
Role of beer lipid-binding proteins in preventing lipid destabilization of foam. J. Agric. Food Chem., 2002, 50. vsk, nro 26, s. 7645–50.
Cornelius AS, Yerram NR, Kratz DA, Spector AA: Cytotoxic effect of cis-parinaric acid in cultured malignant cells. Cancer Res., 1991, 51. vsk, nro 22, s. 6025–30. Artikkelin verkkoversio.

Aiheesta muualla

PubChem: Alpha-parinaric acid (englanniksi)
CaymanChem: cis-Parinaric Acid eli α-Parinaric Acid (englanniksi)
PubChem: Beta-parinaric acid (englanniksi)

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[1] Tsujimoto M, Koyanagi H. (1933). New unsaturated acid in the kernel oil of “akarittom”, “Parinarium laurinum”. I. Kogyo Kagaku Zasshi 36 (Suppl): 110–113.

[isbn0-8342-1342-7-2] Gunstone F.D. (1996). Fatty Acid and Lipid Chemistry. Berlin: Springer Verlag, 10. ISBN 0-8342-1342-7.

[3] Endo S, Zhiping G, Takagi T. (1991). Lipid components of seven species of Basidiomycotina and three species of Ascomycotina. Journal of the Japan Oil Chemists' Society 40(7): 574–577.

[4] Spitzer V, Tomberg W, Zucolotto M. (1996). Identification of alpha-parinaric acid in the seed oil of Sebastiana brasiliensis Sprengel (Euphorbiaceae). Journal of the American Oil Chemists' Society 73(5): 569–573.

[pmid15351273-5] Kuklev DV, Smith WL: Synthesis of four isomers of parinaric acid. Chem. Phys. Lipids, 2004, 131. vsk, nro 2, s. 215–22.

[pmid1057769-6] Conjugated polyene fatty acids as membrane probes: preliminary characterization. Proc. Natl. Acad. Sci. U.S.A., 1975, 72. vsk, nro 5, s. 1649–53.

[7] Berde CB, Kerner JA, Johnson JD. (1980). Use of the conjugated polyene fatty-acid parinaric-acid in assaying fatty-acids in serum or plasma. Clinical Chemistry 26(8): 1173–1177.

[8] Townsend A-A, Nakai S. (1983). Relationships between hydrophobicity and foaming characteristics of food proteins. Journal of Food Science 48(2): 588–594.

[9] Zhu H, Damodaran S. (1994). Heat-induced conformational changes in whey protein isolate and its relation to foaming properties. Journal of Agricultural and Food Chemistry 42(4): 846–855.

[pmid12475284-10] Role of beer lipid-binding proteins in preventing lipid destabilization of foam. J. Agric. Food Chem., 2002, 50. vsk, nro 26, s. 7645–50.

[pmid1933865-11] Cornelius AS, Yerram NR, Kratz DA, Spector AA: Cytotoxic effect of cis-parinaric acid in cultured malignant cells. Cancer Res., 1991, 51. vsk, nro 22, s. 6025–30. Artikkelin verkkoversio.