fbpx
Wikipedia

Vaccenic acid

February 15, 2024

Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt.[1][2] Trans fat in human milk may depend on trans fat content in food.[3][4]

Vaccenic acid
Names
Preferred IUPAC name
(11E)-Octadec-11-enoic acid
Identifiers
  • 693-72-1 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28727 Y
ChemSpider
  • 4444571 Y
ECHA InfoCard 100.010.691
  • 5281127
UNII
  • GQ72OGU4EV Y
  • DTXSID301009341
  • 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+ Y
    Key: UWHZIFQPPBDJPM-BQYQJAHWSA-N Y
  • 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 their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow).[4]

Vaccenic acid was discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid,[5][6] where it shows anticarcinogenic properties.[7]

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

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

Health edit

Two Canadian studies have shown that vaccenic acid could hold benefits over trans fats derived from vegetable shortenings, or a mixture of pork lard and soy fat, by lowering total LDL and triglyceride levels.[10][11][12][13][14] A study by the US Department of Agriculture showed that vaccenic acid raises both HDL and 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 total cholesterol, LDL cholesterol and lower triglyceride levels,[16] with an effect comparable to CLA. This effect was not seen in lean rats.[17]

Vaccenic acid accumulates in the orbitofrontal cortex to a higher extent in patients with bipolar disorder and schizophrenia.[18][19]

Oxidation of omega-7 unsaturated fatty acids on the skin surface, such as palmitoleic acid and vaccenic acid, may be the cause of the phenomenon commonly known as old 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 activating CD8+ T cells. This effect is accomplished by deactivating a GPR43 receptor, which activates the CREB pathway 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. PMID 10481820.
  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. PMID 16988126.
  4. ^ a b Destaillats 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. PMID 15653508.
  5. ^ Bauman, Dale. . Archived from the original on 2006-09-07. Retrieved 2007-01-15.
  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. PMID 12094634. S2CID 2920114.
  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. PMID 15465769. Retrieved 2007-01-15.
  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. ISSN 1932-6203. PMC 4773160. PMID 26930646.
  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. PMID 19923390.
  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. PMID 19923390.
  15. ^ David J. Baer, PhD. US Department of Agriculture, Agricultural Research Service, Beltsville Human Nutrition Research Laboratory. , IDF World Dairy Summit 2010, 8–11 November 2010. Auckland, New Zealand
  16. ^ AFNS. Alberta natural trans fat research earns global recognition 2008-06-15 at the Wayback 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. ISSN 0956-666X.
  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. PMC 1853256. PMID 17236749.
  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. PMC 2620106. PMID 18715653.
  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. PMID 11286617.
  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. PMID 27269708.
  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. PMC 10686835. PMID 37993715.

February 15, 2024
vaccenic, acid, naturally, occurring, trans, fatty, acid, omega, fatty, acid, predominant, kind, trans, fatty, acid, found, human, milk, ruminants, dairy, products, such, milk, butter, yogurt, trans, human, milk, depend, trans, content, food, namespreferred, i. Vaccenic acid is a naturally occurring trans fatty acid and an omega 7 fatty acid It is the predominant kind of trans fatty acid found in human milk in the fat of ruminants and in dairy products such as milk butter and yogurt 1 2 Trans fat in human milk may depend on trans fat content in food 3 4 Vaccenic acid NamesPreferred IUPAC name 11E Octadec 11 enoic acidIdentifiersCAS Number 693 72 1 Y3D model JSmol Interactive imageChEBI CHEBI 28727 YChemSpider 4444571 YECHA InfoCard 100 010 691PubChem CID 5281127UNII GQ72OGU4EV YCompTox Dashboard EPA DTXSID301009341InChI 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 YKey UWHZIFQPPBDJPM BQYQJAHWSA N YInChI 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 BQYQJAHWBKSMILES CCCCCC C C CCCCCCCCCC O OPropertiesChemical formula C 18H 34O 2Molar mass 282 461 g molMelting point 44 C 111 F Boiling point 172 C 342 F Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Its IUPAC name is 11E 11 octadecenoic acid and its lipid shorthand name is 18 1 trans 11 The name was derived from the Latin vacca cow 4 Vaccenic acid was discovered in 1928 in animal fats and butter Mammals convert it into rumenic acid a conjugated linoleic acid 5 6 where it shows anticarcinogenic properties 7 Its stereoisomer cis vaccenic acid is found in Sea Buckthorn Hippophae rhamnoides oil 8 Its IUPAC name is 11Z 11 octadecenoic acid and its lipid shorthand name is 18 1 cis 11 Cows milk had highest trans vaccenic acid content in the first few days of the cows being milked 9 indicating that it is stockpiled similarly to omega 3 fatty acids Health editTwo Canadian studies have shown that vaccenic acid could hold benefits over trans fats derived from vegetable shortenings or a mixture of pork lard and soy fat by lowering total LDL and triglyceride levels 10 11 12 13 14 A study by the US Department of Agriculture showed that vaccenic acid raises both HDL and 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 total cholesterol LDL cholesterol and lower triglyceride levels 16 with an effect comparable to CLA This effect was not seen in lean rats 17 Vaccenic acid accumulates in the orbitofrontal cortex to a higher extent in patients with bipolar disorder and schizophrenia 18 19 Oxidation of omega 7 unsaturated fatty acids on the skin surface such as palmitoleic acid and vaccenic acid may be the cause of the phenomenon commonly known as old 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 activating CD8 T cells This effect is accomplished by deactivating a GPR43 receptor which activates the CREB pathway instead The effect was produced with a diet containing 1 w w TVA 22 References edit Bowerman Susan May 19 2008 Now there are good trans fats Los Angeles Times 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 lt 233 AID FOOD233 gt 3 0 CO 2 B PMID 10481820 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 PMID 16988126 a b Destaillats 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 PMID 15653508 Bauman Dale cis 9 trans 11 CLA A Potent Anticarcinogen Found in Milk Fat Archived from the original on 2006 09 07 Retrieved 2007 01 15 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 PMID 12094634 S2CID 2920114 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 PMID 15465769 Retrieved 2007 01 15 Federal Research Centre for Nutrition and Food Institute for Lipid Research Seed Oil Fatty Acids Database Bainbridge Melissa L Cersosimo Laura M Wright Andre 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 ISSN 1932 6203 PMC 4773160 PMID 26930646 Trans Fats From Ruminant Animals May Be Beneficial Health News redOrbit 8 September 2011 Retrieved 22 January 2013 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 PMID 19923390 Wang Flora amp Proctor Spencer 2 April 2008 Natural trans fats have health benefits University of Alberta study shows Press release University of Alberta 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 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 PMID 19923390 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 AFNS Alberta natural trans fat research earns global recognition Archived 2008 06 15 at the Wayback Machine April 2 2008 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 ISSN 0956 666X 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 PMC 1853256 PMID 17236749 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 PMC 2620106 PMID 18715653 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 PMID 11286617 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 PMID 27269708 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 PMC 10686835 PMID 37993715 Retrieved from https en wikipedia org w index php title Vaccenic acid amp oldid 1197433966, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.