Vakseenihappo

Vakseenihappo
Tunnisteet
CAS-numero	(trans) 693-72-1 (trans)
IUPAC-nimi	(E)-octadek-11-eenihappo
SMILES	CCCCCCC=CCCCCCCCCCC(=O)O
Ominaisuudet
Kemiallinen kaava	C18H34O2
Moolimassa	282,461 g/mol
Sulamispiste	44 °C (trans)
	Infobox OKVirheellinen NIMI-arvo

Vakseenihappo on omega-7-rasvahappo. Se on luonnollinen transrasvahappo, jota esiintyy märehtijöiden rasvassa sekä maitotuotteissa kuten maidossa, voissa ja jogurtissa.[1] Vakseenihappo on hallitseva rasvahappo myös ihmisen maidossa esiintyvässä transrasvassa.[2][3]

Vakseenihapon nimi on johdettu latinan lehmää tarkoittavasta sanasta vacca.[4] Sen IUPAC-nimi on (E)-11-oktadekeenihappo ja lipidilyhytnimi 18:1 trans-11.

Vakseenihappo löydettiin vuonna 1928 eläinrasvoista ja voista. Se on pääasiallinen transrasvahappo-isomeeri maitorasvassa.[4] Nisäkkäät muuttavat sen delta-9-desaturaasin avulla rumeenihapoksi, joka on konjugoitu linolihappo (CLA),[5][6] jolloin sillä esiintyy antikarsinogeenisia ominaisuuksia.[7]

Vakseenihapon stereoisomeeria, cis-vakseenihappoa, joka sekin on omega-7-rasvahappo, esiintyy tyrnimarjojen öljyssä.[8] Sen IUPAC-nimi on (Z)-11-oktadekeenihappo, lipidilyhytnimi 18:1 cis-11 ja CAS-numero 506-17-2.

Terveysvaikutukset

Vuonna 2008 Albertan yliopistossa tehty tutkimus antoi viitteitä siitä, että rottien ruokinta vakseenihapolla 16 viikon ajanjaksolla sai aikaan kokonaiskolesterolin, LDL-kolesterolin ja triglyseridien pitoisuuksien alenemisen. Tutkijat valmistelevat jatkotutkimusten suorittamista, mukaan lukien kliinisiä tutkimuksia.[9]

Vakseenihappoa on löydetty poikkeavasti orbitofrontaalisesta korteksista bipolaarihäiriötä ja skitsofreniaa sairastaneilta potilailta.[10][11]

Tyydyttymättömien omega-7-rasvahappojen kuten palmitoleiinihapon ja vakseenihapon hapettuminen ihon pinnalla 2-nonenaaliksi saattaa olla vanhan henkilön hajuksi kutsutun ilmiön syynä.[12]

Lähteet

Natural trans fats may be good for you. May 19, 2008
Precht, D and J.Molkentin C18:1, C18:2, and C8:3 trans and cis fatty acid isomers including conjugated cis delta 9, trans delta 11 linoleic acid (CLA) as well as total fat composition of German human milk lipids, Nahrung 1999 43(4) 233–244
Friesen, R, and S.M. Innis, Trans Fatty acids in Human milk in Canada declined with the introduction of trans fat food labeling, J. Nut 2006, 136 2558–2561
F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida (2005). "Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats". J. Dairy Sci 88 (449). Viitattu 2007-01-16.
Bauman, Dale: cis-9, trans-11 CLA – A Potent Anticarcinogen Found in Milk Fat ansci.cornell.edu. Arkistoitu 7.9.2006. Viitattu 15.1.2007.
Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C (2001). "Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland". Nutr Cancer 41 (1-2): 91–7. doi:10.1207/S15327914NC41-1&2_12. PMID 12094634. Viitattu 2007-01-15.
Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C. (October 1, 2004). "The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats". J Nutr 134 (10): 2698–704. PMID 15465769. Viitattu 2007-01-15.
Federal Research Centre for Nutrition and Food – Institute for Lipid Research: Seed Oil Fatty Acids Database bagkf.de.
AFNS. Alberta natural trans fat research earns global recognition. Apr 2, 2008.
"Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications." (2007). Schizophr Res 91 (1-3): 37–50. doi:10.1016/j.schres.2006.11.027. PMID 17236749.
"Deficits in docosahexaenoic acid and associated elevations in the metabolism of arachidonic acid and saturated fatty acids in the postmortem orbitofrontal cortex of patients with bipolar disorder." (2008). Psychiatry Research 160 (3): 285–299. doi:10.1016/j.psychres.2007.08.021. PMID 18715653.
S. Haze, Y. Gozu, S. Nakamura, Y. Kohno, K. Sawano, H. Ohta and K. Yamazaki (2001). "2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging". Journal of Investigative Dermatology 116 (4): 520–524. doi:10.1046/j.0022-202x.2001.01287.x. PMID 11286617.

Aiheesta muualla

PubChem: Vaccenic acid (englanniksi)
PubChem: cis-Vaccenic acid (englanniksi)
Human Metabolome Database: Vaccenic acid (englanniksi)
Human Metabolome Database: cis-Vaccenic acid (englanniksi)
Food Component Database (FooDB): Vaccenic acid (englanniksi)
Kyoto Encyclopedia of Genes and Genomes (KEGG): Vaccenic acid (englanniksi)

Rasvahapot

Tyydyttyneet	Etikkahappo (C2) · Propionihappo (C3) · Voihappo (C4) · Valeriaanahappo (C5) · Kapronihappo (C6) · Enantyylihappo (C7) · Kapryylihappo (C8) · Pelargonihappo (C9) · Kapriinihappo (C10) · Hendekaanihappo (C11) · Lauriinihappo (C12) · Tridekyylihappo (C13) · Myristiinihappo (C14) · Pentadekyylihappo (C15) · Palmitiinihappo (C16) · Margariinihappo (C17) · Steariinihappo (C18) · Nonadekyylihappo (C19) · Arakidihappo (C20) · Heneikosyylihappo (C21) · Beheenihappo (C22) · Trikosyylihappo (C23) · Lignoseriinihappo (C24) · Pentakosyylihappo (C25) · Keroottihappo (C26) · Heptakosyylihappo (C27) · Montaanihappo (C28) · Nonakosyylihappo (C29) · Melissiinihappo (C30) · Henatriakontyylihappo (C31) · Lakkerihappo (C32) · Psylliinihappo (C33) · Geddiinihappo (C34) · Keromuovihappo (C35) · Heksatriakontyylihappo (C36)
Omega-1	Undekyleenihappo (11:1)
Omega-3	Alfalinoleenihappo (18:3) · Rumeleenihappo (18:3) · Parinaarihappo (18:4) · Stearidonihappo (18:4) · Eikosapentaeenihappo (20:5) · Dokosaheksaeenihappo (22:6)
Omega-5	Myristoleiinihappo (14:1) · Granaattiomenahappo (18:3) · Trumpettipuuhappo (18:3)
Omega-6	Linolihappo (18:2) · γ-linoleenihappo (18:3) · Kehäkukkahappo (18:3) · Pinoleenihappo (18:3) · Dihomo-γ-linoleenihappo (20:3) · Podokarpiinihappo (20:3) · Arakidonihappo (20:4) · Dokosatetraeenihappo (22:4)
Omega-7	Palmitoleiinihappo (16:1) · Vakseenihappo (trans-18:1) · Rumeenihappo (18:2) · Paulliinihappo (20:1)
Omega-9	Oleiinihappo (18:1) · Elaidiinihappo (trans-18:1) · Eikoseenihappo (20:1) · Erukahappo (22:1) · Nervonihappo (24:1) · Meadin happo (20:3)
Omega-12	Petroseliinihappo (18:1)

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[1] Natural trans fats may be good for you. May 19, 2008

[2] Precht, D and J.Molkentin C18:1, C18:2, and C8:3 trans and cis fatty acid isomers including conjugated cis delta 9, trans delta 11 linoleic acid (CLA) as well as total fat composition of German human milk lipids, Nahrung 1999 43(4) 233–244

[3] Friesen, R, and S.M. Innis, Trans Fatty acids in Human milk in Canada declined with the introduction of trans fat food labeling, J. Nut 2006, 136 2558–2561

[Destaillats-4] F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida (2005). "Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats". J. Dairy Sci 88 (449). Viitattu 2007-01-16.

[Bauman-5] Bauman, Dale: cis-9, trans-11 CLA – A Potent Anticarcinogen Found in Milk Fat ansci.cornell.edu. Arkistoitu 7.9.2006. Viitattu 15.1.2007.

[Banni-6] Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C (2001). "Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland". Nutr Cancer 41 (1-2): 91–7. doi:10.1207/S15327914NC41-1&2_12. PMID 12094634. Viitattu 2007-01-15.

[lock-7] Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C. (October 1, 2004). "The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats". J Nutr 134 (10): 2698–704. PMID 15465769. Viitattu 2007-01-15.

[sofa-8] Federal Research Centre for Nutrition and Food – Institute for Lipid Research: Seed Oil Fatty Acids Database bagkf.de.

[9] AFNS. Alberta natural trans fat research earns global recognition. Apr 2, 2008.

[10] "Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications." (2007). Schizophr Res 91 (1-3): 37–50. doi:10.1016/j.schres.2006.11.027. PMID 17236749.

[11] "Deficits in docosahexaenoic acid and associated elevations in the metabolism of arachidonic acid and saturated fatty acids in the postmortem orbitofrontal cortex of patients with bipolar disorder." (2008). Psychiatry Research 160 (3): 285–299. doi:10.1016/j.psychres.2007.08.021. PMID 18715653.

[12] S. Haze, Y. Gozu, S. Nakamura, Y. Kohno, K. Sawano, H. Ohta and K. Yamazaki (2001). "2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging". Journal of Investigative Dermatology 116 (4): 520–524. doi:10.1046/j.0022-202x.2001.01287.x. PMID 11286617.