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Revision as of 06:43, 18 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Saving copy of the {{chembox}} taken from revid 477483892 of page Vaccenic_acid for the Chem/Drugbox validation project (updated: 'ChEBI').		Latest revision as of 19:10, 8 January 2025 edit InternetArchiveBot (talk | contribs)Bots, Pending changes reviewers5,388,257 edits Rescuing 1 sources and tagging 0 as dead.) #IABot (v2.0.9.5) (Whoop whoop pull up - 22424
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			{{Short description|Trans-unsaturated fatty acid}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
	| verifiedrevid = 452887604		| verifiedrevid = 477493783
	| Name = Vaccenic acid		| Name = Vaccenic acid
	| ImageFile = Trans-vaccenic acid.svg		| ImageFile = Trans-vaccenic acid.svg
	| ImageSize = 250px		| ImageSize = 250px
	| ImageName = Skeletal formula		| ImageName = Skeletal formula
	| ImageFile1 = Vaccenic-acid-3D-balls.png		| ImageFile1 = Vaccenic-acid-3D-balls.png
	| ImageSize1 = 250px		| ImageSize1 = 250px
	| ImageName1 = Ball-and-stick model		| ImageName1 = Ball-and-stick model
	| IUPACName = (E)-Octadec-11-enoic acid		| PIN = (11''E'')-Octadec-11-enoic acid
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 693-72-1		| CASNo = 693-72-1
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| ChEBI = 28727
			| UNII = GQ72OGU4EV
			| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| ChEBI = 28727
	| PubChem = 5281127		| PubChem = 5281127
	| SMILES = CCCCCC/C=C/CCCCCCCCCC(O)=O		| SMILES = CCCCCC/C=C/CCCCCCCCCC(O)=O
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChEBI = 28727
	| PubChem = 5281127
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4444571		| ChemSpiderID = 4444571
	| 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+		| 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+
	| InChIKey = UWHZIFQPPBDJPM-BQYQJAHWBK		| InChIKey = UWHZIFQPPBDJPM-BQYQJAHWBK
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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+		| StdInChI = 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+
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = UWHZIFQPPBDJPM-BQYQJAHWSA-N		| StdInChIKey = UWHZIFQPPBDJPM-BQYQJAHWSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>18</sub>H<sub>34</sub>O<sub>2</sub>		| C = 18 |H = 34 |O = 2
	| MolarMass = 282.461 g/mol		| MolarMass = 282.461 g/mol
	| Density =		| Density =
	| MeltingPt =		| MeltingPt = {{convert|44|C|F}}
	| BoilingPt =		| BoilingPt = {{convert|172|C|F}}
	}}		}}
	}}		}}
			'''Vaccenic acid''' is a naturally occurring ] and an ]. It is the predominant kind of trans-fatty acid found in ], in the fat of ]s, and in ]s such as ], ], and ].<ref>{{Cite web |url=https://www.latimes.com/archives/la-xpm-2008-may-19-he-eat19-story.html |title=Now there are good trans fats? |last=Bowerman |first=Susan |date=May 19, 2008 |website=Los Angeles Times}}</ref><ref name="pmid10481820">{{Cite journal |vauthors=Precht D, Molkentin J |date=August 1999 |title=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 |journal=Nahrung |volume=43 |issue=4 |pages=233–44 |doi=10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B |pmid=10481820}}</ref>
			Trans fat in human milk may depend on trans fat content in food.<ref name="pmid16988126">{{Cite journal |vauthors=Friesen R, Innis SM |date=October 2006 |title=Trans fatty acids in human milk in Canada declined with the introduction of trans fat food labeling |journal=J. Nutr. |volume=136 |issue=10 |pages=2558–61 |doi=10.1093/jn/136.10.2558 |pmid=16988126 |doi-access=free}}</ref><ref name=Destaillats/> Vaccenic acid was discovered in 1928 in ]s and ].
			Mammals convert it into ], a ],<ref name=Bauman>{{Cite web |url=http://www.ansci.cornell.edu/bauman/human_health/index.htm |title=cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat |last=Bauman, Dale |archive-url=https://web.archive.org/web/20060907102559/http://www.ansci.cornell.edu/bauman/human_health/index.htm <!-- Bot retrieved archive --> |archive-date=2006-09-07 |access-date=2007-01-15}}</ref><ref name="Banni">{{Cite journal |vauthors=Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C |year=2001 |title=Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland |journal=Nutr Cancer |volume=41 |issue=1–2 |pages=91–7 |doi=10.1080/01635581.2001.9680617 |pmid=12094634|s2cid=2920114 }}</ref>
			where it shows anticarcinogenic properties.<ref name="lock">{{Cite journal |vauthors=Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C |date=October 1, 2004 |title=The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats |url=http://jn.nutrition.org/cgi/content/abstract/134/10/2698 |journal=J Nutr |volume=134 |issue=10 |pages=2698–704 |doi=10.1093/jn/134.10.2698 |pmid=15465769 |access-date=2007-01-15|doi-access=free }}</ref> Cows milk had highest trans-vaccenic acid content in the first few days of the cows being ],<ref>{{Cite journal |last1=Bainbridge |first1=Melissa L. |last2=Cersosimo |first2=Laura M. |last3=Wright |first3=André-Denis G. |last4=Kraft |first4=Jana |date=2016-03-01 |editor-last=Brockmann |editor-first=Gudrun A. |title=Content and Composition of Branched-Chain Fatty Acids in Bovine Milk Are Affected by Lactation Stage and Breed of Dairy Cow |journal=PLOS ONE |language=en |volume=11 |issue=3 |pages=e0150386 |doi=10.1371/journal.pone.0150386 |doi-access=free |issn=1932-6203 |pmc=4773160 |pmid=26930646|bibcode=2016PLoSO..1150386B }}</ref> indicating that it is stockpiled similarly to ].
			Its ] name is '''(11''E'')-11-octadecenoic acid''', and its lipid shorthand name is '''18:1 ''trans''-11'''. The name was derived from the ] ''vacca'' (]).<ref name="Destaillats">{{Cite journal |vauthors=Destaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F |year=2005 |title=Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats |journal=] |volume=88 |issue=449 |pages=449 |doi=10.3168/jds.S0022-0302(05)72705-3 |pmid=15653508 |doi-access=free}}</ref> Its stereoisomer, '''''cis''-vaccenic acid''', is found in ] (''Hippophae rhamnoides'') oil.<ref name="sofa">{{Cite web |url=http://www.bagkf.de/sofa/ |title=Seed Oil Fatty Acids Database |last=Federal Research Centre for Nutrition and Food - Institute for Lipid Research}}</ref> Its ] name is (11''Z'')-11-octadecenoic acid, and its lipid shorthand name is 18:1 ''cis''-11.
			==Health effects==
			Two Canadian studies have shown that vaccenic acid could hold benefits over trans fats derived from vegetable ]s, or a mixture of pork ] and soy fat, by lowering total ] and triglyceride levels.<ref>. redOrbit (8 September 2011). Retrieved 22 January 2013.</ref><ref name="jn.nutrition">{{cite journal|journal=The Journal of Nutrition|volume=140|issue=1|date=Jan 2010|pages=18–24|pmid=19923390|doi=10.3945/jn.109.105163|title=Dietary Vaccenic Acid Has Antiatherogenic Effects in LDLr-/- Mice|last1=Bassett|first1=C. M. C.|last2=Edel|first2=A. L.|last3=Patenaude|first3=A. F.|last4=McCullough|first4=R. S.|last5=Blackwood|first5=D. P.|last6=Chouinard|first6=P. Y.|last7=Paquin|first7=P.|last8=Lamarche|first8=B.|last9=Pierce|first9=G. N.|doi-access=free}}</ref><ref>{{cite press release|publisher=University of Alberta|url=http://www.eurekalert.org/pub_releases/2008-04/uoa-ntf040208.php|title=Natural trans fats have health benefits, University of Alberta study shows|date=2 April 2008|last1=Wang|first1=Flora|last2=Proctor|first2=Spencer|name-list-style=amp|access-date=14 October 2021|archive-date=17 December 2011|archive-url=https://web.archive.org/web/20111217080529/http://www.eurekalert.org/pub_releases/2008-04/uoa-ntf040208.php|url-status=dead}}</ref><ref>{{cite journal|vauthors=Wang Y, Jacome-Sosa MM, Vine DF, Proctor SD |title=Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans-fats to improve CVD risk|date=20 May 2010|journal=Lipid Technology|volume=22|issue=5|pages=103–106|doi=10.1002/lite.201000016}}</ref><ref>{{cite journal|vauthors=Bassett C, Edel AL, Patenaude AF, McCullough RS, Blackwood DP, Chouinard PY, Paquin P, Lamarche B, Pierce GN |title=Dietary Vaccenic Acid Has Antiatherogenic Effects in LDLr−/− Mice|year=2010|journal=The Journal of Nutrition|volume=140|issue=1|pages=18–24|doi=10.3945/jn.109.105163|pmid=19923390|doi-access=free}}</ref> A study by the US Department of Agriculture showed that vaccenic acid raises both ] and LDL cholesterol, whereas industrial trans fats only raise LDL with no beneficial effect on HDL.<ref>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</ref>
			Obese rats fed a diet enriched with vaccenic acid for 16 weeks had a reduction in total ], ] cholesterol and lower ] levels,<ref>AFNS. {{Webarchive|url=https://web.archive.org/web/20080615014134/http://www.ales.ualberta.ca/afns/news.cfm?story=75846 |date=2008-06-15 }}. April 2, 2008.</ref> with an effect comparable to ]. This effect was not seen in lean rats.<ref>{{Cite journal |last1=Wang |first1=Ye |last2=Jacome-Sosa |first2=M. Miriam |last3=Vine |first3=Donna F. |last4=Proctor |first4=Spencer D. |date=May 2010 |title=Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans -fats to improve CVD risk |url=https://onlinelibrary.wiley.com/doi/10.1002/lite.201000016 |journal=Lipid Technology |language=en |volume=22 |issue=5 |pages=103–106 |doi=10.1002/lite.201000016 |issn=0956-666X}}</ref>
			Vaccenic acid accumulates in the ] to a higher extent in patients with ] and ].<ref>{{Cite journal |last1=McNamara |first1=RK |last2=Jandacek |first2=R |last3=Rider |first3=T |last4=Tso |first4=P |last5=Hahn |first5=CG |last6=Richtand |first6=NM |last7=Stanford |first7=KE |year=2007 |title=Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications |journal=Schizophr Res |volume=91 |issue=1–3 |pages=37–50 |doi=10.1016/j.schres.2006.11.027 |pmc=1853256 |pmid=17236749}}</ref><ref>{{Cite journal |last1=McNamara |first1=RK |last2=Jandacek |first2=R |last3=Rider |first3=T |last4=Tso |first4=P |last5=Stanford |first5=KE |last6=Hahn |first6=CG |last7=Richtand |first7=NM |year=2008 |title=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 |journal=Psychiatry Research |volume=160 |issue=3 |pages=285–299 |doi=10.1016/j.psychres.2007.08.021 |pmc=2620106 |pmid=18715653}}</ref>
			Oxidation of ] on the skin surface, such as ] and vaccenic acid, may be the cause of the phenomenon commonly known as ].<ref name="pmid11286617">{{Cite journal |vauthors=Haze S, Gozu Y, Nakamura S, Kohno Y, Sawano K, Ohta H, Yamazaki K |date=April 2001 |title=2-Nonenal newly found in human body odor tends to increase with aging |journal=J. Invest. Dermatol. |volume=116 |issue=4 |pages=520–4 |doi=10.1046/j.0022-202x.2001.01287.x |pmid=11286617|doi-access=free }}</ref>
			Alkaline phosphatase was inhibited 25% by vaccenic acid in osteoblasts.<ref name="pmid27269708">{{Cite journal |vauthors=Hamazaki K, Suzuki N, Kitamura K, Hattori A, Nagasawa T, Itomura M, Hamazaki T |date=June 2016 |title=Is vaccenic acid (18:1t n-7) associated with an increased incidence of hip fracture? An explanation for the calcium paradox |journal=Prostaglandins Leukot. Essent. Fatty Acids |volume=109 |pages=8–12 |doi=10.1016/j.plefa.2016.04.001 |pmid=27269708}}</ref>
			A 2023 University of Chicago study found that trans-vaccenic acid enhances anti-tumor immunity by activating ] ]. This effect is accomplished by deactivating a ] receptor, which activates the ] pathway instead. The effect was produced with a diet containing 1% w/w TVA.<ref>{{cite journal|vauthors=Fan H, Xia S, Xiang J et al. |title=Trans-vaccenic acid reprograms CD8+ T cells and anti-tumour immunity |date=22 November 2023 |journal=Nature |volume=623 |issue=7989 |pages=1034–1043 |doi=10.1038/s41586-023-06749-3|doi-access=free |pmid=37993715 |pmc=10686835 }}</ref>
			==References==
			{{reflist}}
			{{Fatty acids}}
			]
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