词条 | Vaccenic acid |
释义 |
| verifiedrevid = 477493783 | Name = Vaccenic acid | ImageFile = Trans-vaccenic acid.svg | ImageSize = 250px | ImageName = Skeletal formula | ImageFile1 = Vaccenic-acid-3D-balls.png | ImageSize1 = 250px | ImageName1 = Ball-and-stick model | IUPACName = (11E)-Octadec-11-enoic acid |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 693-72-1 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 28727 | PubChem = 5281127 | SMILES = CCCCCC/C=C/CCCCCCCCCC(O)=O | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | 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+ | InChIKey = UWHZIFQPPBDJPM-BQYQJAHWBK | 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+ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = UWHZIFQPPBDJPM-BQYQJAHWSA-N |Section2={{Chembox Properties | Formula = C18H34O2 | MolarMass = 282.461 g/mol | Density = | MeltingPt = {{convert|44|C|F}} | BoilingPt = {{convert|172|C|F}} }}Vaccenic acid, also known as (11E)-octadec-11-enoic acid is a naturally occurring trans-fatty acid found in the fat of ruminants and in dairy products such as milk, butter, and yogurt.[1] It is also the predominant fatty acid comprising trans fat in human milk.[2][3] 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. It is the main trans fatty acid isomer present in milk fat.[4] Mammals convert it into rumenic acid, a conjugated linoleic acid,[5][6] where it shows anticarcinogenic properties.[7] Its stereoisomer, cis-vaccenic acid, is an omega-7 fatty 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. HealthA 2008 study at the University of Alberta suggests that vaccenic acid feeding in rats over 16 weeks resulted in lowered total cholesterol, lowered LDL cholesterol and lower triglyceride levels. The researchers are preparing to conduct further research, including human clinical trials.[9] Vaccenic acid is also found in human orbitofrontal cortex of patients with bipolar disorder and schizophrenia.[10][11] Alkaline phosphatase inhibited 25% by vaccenic acid in osteoblasts.[12] 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.[13] References1. ^{{cite web |url=http://articles.latimes.com/2008/may/19/health/he-eat19 |title=Now there are good trans fats? |last=Bowerman |first= Susan|date= May 19, 2008 |website=Los Angeles Times |publisher= |access-date= }} {{Fatty acids}}2. ^{{cite journal | vauthors = Precht D, Molkentin J | 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 | date = August 1999 | pmid = 10481820 | doi = 10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B }} 3. ^{{cite journal | vauthors = Friesen R, Innis SM | 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 | date = October 2006 | pmid = 16988126 }} 4. ^1 {{cite journal |journal= Journal of Dairy Science|volume=88|issue=449|year=2005 |title=Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats |vauthors = Destaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F |doi= 10.3168/jds.S0022-0302(05)72705-3 |pages= 449}} 5. ^{{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 |author = Bauman, Dale |accessdate=2007-01-15 |archiveurl = https://web.archive.org/web/20060907102559/http://www.ansci.cornell.edu/bauman/human_health/index.htm |archivedate = 2006-09-07}} 6. ^{{cite journal |vauthors=Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C |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 |year=2001 |pmid=12094634 |doi=10.1080/01635581.2001.9680617}} 7. ^{{cite journal |url =http://jn.nutrition.org/cgi/content/abstract/134/10/2698| journal=J Nutr|volume=134|pages=2698–704 |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 |vauthors=Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C |accessdate=2007-01-15 |pmid= 15465769 |issue =10 |date = October 1, 2004 }} 8. ^{{cite web|url =http://www.bagkf.de/sofa/ |author= Federal Research Centre for Nutrition and Food - Institute for Lipid Research|title=Seed Oil Fatty Acids Database}} 9. ^AFNS. Alberta natural trans fat research earns global recognition {{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. 10. ^{{cite journal | journal = Schizophr Res | year = 2007 | volume = 91 | issue = 1–3 | pages = 37–50 | doi = 10.1016/j.schres.2006.11.027 | pmid = 17236749 | 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 | title = Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications | pmc = 1853256}} 11. ^{{cite journal | journal = Psychiatry Research | volume = 160 | year = 2008 | pages = 285–299 | doi = 10.1016/j.psychres.2007.08.021 | pmid = 18715653 | 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 | 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 | issue = 3 | pmc = 2620106}} 12. ^{{cite journal | vauthors = Hamazaki K, Suzuki N, Kitamura K, Hattori A, Nagasawa T, Itomura M, Hamazaki T | 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 | issue = | pages = 8–12 | date = June 2016 | pmid = 27269708 | doi = 10.1016/j.plefa.2016.04.001 }} 13. ^{{cite journal | vauthors = Haze S, Gozu Y, Nakamura S, Kohno Y, Sawano K, Ohta H, Yamazaki K | 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 | date = April 2001 | pmid = 11286617 | doi = 10.1046/j.0022-202x.2001.01287.x }} 4 : Fatty acids|Animal fats|Dairy products|Alkenoic acids |
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