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Vaccenic acid

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Vaccenic acid
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
(11E)-Octadec-11-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.691Edit this at Wikidata
UNII
  • InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+checkY
    Key: UWHZIFQPPBDJPM-BQYQJAHWSA-NcheckY
  • InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+
    Key: UWHZIFQPPBDJPM-BQYQJAHWBK
  • CCCCCC/C=C/CCCCCCCCCC(O)=O
Properties
C18H34O2
Molar mass 282.461 g/mol
Melting point 44 °C (111 °F)
Boiling point 172 °C (342 °F)
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Vaccenic acidis a naturally occurringtrans fatty acidand anOmega -7 fatty acid.It is the predominant kind of trans-fatty acid found inhuman milk,in the fat ofruminants,and indairy productssuch asmilk,butter,andyogurt.[1][2] Trans fat in human milk may depend on trans fat content in food.[3][4]

ItsIUPACname is(11E)-11-octadecenoic acid,and its lipid shorthand name is18:1trans-11.The name was derived from theLatinvacca(cow).[4]

Vaccenic acid was discovered in 1928 inanimal fatsandbutter. Mammals convert it intorumenic acid,aconjugated linoleic acid,[5][6] where it shows anticarcinogenic properties.[7]

Its stereoisomer,cis-vaccenic acid,is found inSea Buckthorn(Hippophae rhamnoides) oil.[8]ItsIUPACname is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1cis-11.

Cows milk had highest trans-vaccenic acid content in the first few days of the cows beingmilked,[9]indicating that it is stockpiled similarly toOmega -3 fatty acids.

Health[edit]

Two Canadian studies have shown that vaccenic acid could hold benefits over trans fats derived from vegetableshortenings,or a mixture of porklardand soy fat, by lowering totalLDLand triglyceride levels.[10][11][12][13][14]A study by the US Department of Agriculture showed that vaccenic acid raises bothHDLand LDL cholesterol, whereas industrial trans fats only raise LDL with no beneficial effect on HDL.[15]

Obese rats fed a diet enriched with vaccenic acid for 16 weeks had a reduction in totalcholesterol,LDLcholesterol and lowertriglyceridelevels,[16]with an effect comparable toCLA.This effect was not seen in lean rats.[17]

Vaccenic acid accumulates in theorbitofrontal cortexto a higher extent in patients withbipolar disorderandschizophrenia.[18][19]

Oxidation ofOmega -7 unsaturated fatty acidson the skin surface, such aspalmitoleic acidand vaccenic acid, may be the cause of the phenomenon commonly known asold person smell.[20]

Alkaline phosphatase was inhibited 25% by vaccenic acid in osteoblasts.[21]

A 2023 University of Chicago study found that trans-vaccenic acid enhances anti-tumor immunity by activatingCD8+T cells.This effect is accomplished by deactivating aGPR43receptor, which activates theCREBpathway instead. The effect was produced with a diet containing 1% w/w TVA.[22]


References[edit]

  1. ^Bowerman, Susan (May 19, 2008)."Now there are good trans fats?".Los Angeles Times.
  2. ^Precht D, Molkentin J (August 1999). "C18:1, C18:2 and C18:3 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.43(4): 233–44.doi:10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B.PMID10481820.
  3. ^Friesen R, Innis SM (October 2006)."Trans fatty acids in human milk in Canada declined with the introduction of trans fat food labeling".J. Nutr.136(10): 2558–61.doi:10.1093/jn/136.10.2558.PMID16988126.
  4. ^abDestaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F (2005)."Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats".Journal of Dairy Science.88(449): 449.doi:10.3168/jds.S0022-0302(05)72705-3.PMID15653508.
  5. ^Bauman, Dale."cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat".Archived fromthe originalon 2006-09-07.Retrieved2007-01-15.
  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:10.1080/01635581.2001.9680617.PMID12094634.S2CID2920114.
  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.doi:10.1093/jn/134.10.2698.PMID15465769.Retrieved2007-01-15.
  8. ^Federal Research Centre for Nutrition and Food - Institute for Lipid Research."Seed Oil Fatty Acids Database".
  9. ^Bainbridge, Melissa L.; Cersosimo, Laura M.; Wright, André-Denis G.; Kraft, Jana (2016-03-01). Brockmann, Gudrun A. (ed.)."Content and Composition of Branched-Chain Fatty Acids in Bovine Milk Are Affected by Lactation Stage and Breed of Dairy Cow".PLOS ONE.11(3): e0150386.Bibcode:2016PLoSO..1150386B.doi:10.1371/journal.pone.0150386.ISSN1932-6203.PMC4773160.PMID26930646.
  10. ^Trans Fats From Ruminant Animals May Be Beneficial – Health News.redOrbit (8 September 2011). Retrieved 22 January 2013.
  11. ^Bassett, C. M. C.; Edel, A. L.; Patenaude, A. F.; McCullough, R. S.; Blackwood, D. P.; Chouinard, P. Y.; Paquin, P.; Lamarche, B.; Pierce, G. N. (Jan 2010)."Dietary Vaccenic Acid Has Antiatherogenic Effects in LDLr-/- Mice".The Journal of Nutrition.140(1): 18–24.doi:10.3945/jn.109.105163.PMID19923390.
  12. ^Wang, Flora & Proctor, Spencer (2 April 2008)."Natural trans fats have health benefits, University of Alberta study shows"(Press release). University of Alberta.
  13. ^Wang Y, Jacome-Sosa MM, Vine DF, Proctor SD (20 May 2010). "Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans-fats to improve CVD risk".Lipid Technology.22(5): 103–106.doi:10.1002/lite.201000016.
  14. ^Bassett C, Edel AL, Patenaude AF, McCullough RS, Blackwood DP, Chouinard PY, Paquin P, Lamarche B, Pierce GN (2010)."Dietary Vaccenic Acid Has Antiatherogenic Effects in LDLr−/− Mice".The Journal of Nutrition.140(1): 18–24.doi:10.3945/jn.109.105163.PMID19923390.
  15. ^David J. Baer, PhD. US Department of Agriculture, Agricultural Research Service, Beltsville Human Nutrition Research Laboratory.New Findings on Dairy Trans Fat and Heart Disease Risk,IDF World Dairy Summit 2010, 8–11 November 2010. Auckland, New Zealand
  16. ^AFNS.Alberta natural trans fat research earns global recognitionArchived2008-06-15 at theWayback Machine.April 2, 2008.
  17. ^Wang, Ye; Jacome-Sosa, M. Miriam; Vine, Donna F.; Proctor, Spencer D. (May 2010)."Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans -fats to improve CVD risk".Lipid Technology.22(5): 103–106.doi:10.1002/lite.201000016.ISSN0956-666X.
  18. ^McNamara, RK; Jandacek, R; Rider, T; Tso, P; Hahn, CG; Richtand, NM; Stanford, KE (2007)."Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications".Schizophr Res.91(1–3): 37–50.doi:10.1016/j.schres.2006.11.027.PMC1853256.PMID17236749.
  19. ^McNamara, RK; Jandacek, R; Rider, T; Tso, P; Stanford, KE; Hahn, CG; Richtand, NM (2008)."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".Psychiatry Research.160(3): 285–299.doi:10.1016/j.psychres.2007.08.021.PMC2620106.PMID18715653.
  20. ^Haze S, Gozu Y, Nakamura S, Kohno Y, Sawano K, Ohta H, Yamazaki K (April 2001)."2-Nonenal newly found in human body odor tends to increase with aging".J. Invest. Dermatol.116(4): 520–4.doi:10.1046/j.0022-202x.2001.01287.x.PMID11286617.
  21. ^Hamazaki K, Suzuki N, Kitamura K, Hattori A, Nagasawa T, Itomura M, Hamazaki T (June 2016). "Is vaccenic acid (18:1t n-7) associated with an increased incidence of hip fracture? An explanation for the calcium paradox".Prostaglandins Leukot. Essent. Fatty Acids.109:8–12.doi:10.1016/j.plefa.2016.04.001.PMID27269708.
  22. ^Fan H, Xia S, Xiang J, et al. (22 November 2023)."Trans-vaccenic acid reprograms CD8+ T cells and anti-tumour immunity".Nature.623(7989): 1034–1043.doi:10.1038/s41586-023-06749-3.PMC10686835.PMID37993715.
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