Vaccenic acid

Vaccenic acid
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
(11E)-Octadec-11-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.691
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-N checkY
  • 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).
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Infobox references

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] Vaccenic acid was discovered in 1928 in animal fats and butter.

Mammals (including humans) convert it into rumenic acid, a conjugated linoleic acid. This reaction is mediated by delta-9 desaturase.[3][4]

Cow milk had highest vaccenic acid content in the first few days of milking.[5]

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).[6] Its stereoisomer, cis-vaccenic acid, is found in sea buckthorn (Hippophae rhamnoides) oil.[7] Its IUPAC name is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

References

  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. ^ Kuhnt K, Kraft J, Moeckel P, Jahreis G (April 2006). "Trans-11-18 : 1 is effectively Delta9-desaturated compared with trans-12-18 : 1 in humans". Br J Nutr. 95 (4): 752–761. doi:10.1079/BJN20051680. PMID 16571155.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ Matthäus B (15 October 2012). "The New Database of Seed Oil Fatty Acids". Lipid Technology. 24 (10). doi:10.1002/lite.201200227.
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