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Chemical compound
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]
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.
^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<233::AID-FOOD233>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.
^ 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. 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, 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.
Vaccenicacid 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...
(E)-octadec-9-enoic acid, numerical representation 18:1 (9), n-9, molecular weight 282.46, melting point 43–45 °C. CAS Registry Number 112-79-8. Vaccenicacid has 18...
TFAs are represented by elaidic acid and linolelaidic acid. Their presence is linked heart diseases. The TFA vaccenicacid, which is of animal origin, poses...
oleic acid, such as vaccenicacid, which is converted to CLA by delta-9-desaturase. In healthy humans, CLA and the related conjugated linolenic acid (CLNA)...
These naturally occurring trans fats include conjugated linoleic acid (CLA) and vaccenicacid. They arise from the action of bacteria in the rumen. In contrast...
from ruminants. The predominant kind of trans fat found in milk is vaccenic fatty acid. Trans fats may be also found in some industrially produced foods...
of total fat. Natural TFAs, which include conjugated linoleic acid (CLA) and vaccenicacid, originate in the rumen of these animals. CLA has two double...
acid. Almost invariably that fatty acid is oleic acid (18:1 n−9). Palmitoleic acid (16:1 n−7) and cis-vaccenicacid (18:1 n−7) occur in small amounts in...
Rumenic acid is produced from vaccenicacid by the action of unsaturase enzymes. Rumenic acid is converted back to vaccenicacid en route to stearic acid F...
a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched...
g/mol, exact mass: 282.2559 u) may refer to: Elaidic acid Oleic acid Petroselinic acidVaccenicacid This set index page lists chemical structure articles...
oleic acid (O-P-O triglycerides), and also lipids with trans bonds (see: trans fat). The lipids are vaccenicacid, and conjugated linoleic acid (CLA)...
milk may contain significantly more beneficial omega-3 fatty acids and vaccenicacid than raw conventional milk. The authors found no significant differences...
This definition excludes specifically the trans fats (vaccenicacid and conjugated linoleic acid) that are present especially in human milk, dairy products...
Name Image Origin Description Vaccenicacid An omega-7 fatty acid. It is a naturally occurring trans-fatty acid found in the fat of ruminants and in dairy...
components of the fatty acids produced are palmitic acid (C 16:0), cis-vaccenicacid (C 18:1ω7 c/C 18:1ω6 c) and lauric acid (C 12:0), by which Snodgrassella...
2012). "Conjugated linoleic acid synthesis-related protein proteasome subunit α 5 (PSMA5) is increased by vaccenicacid treatment in goat mammary tissue"...
2012). "Conjugated linoleic acid synthesis-related protein proteasome subunit α 5 (PSMA5) is increased by vaccenicacid treatment in goat mammary tissue"...
2012). "Conjugated linoleic acid synthesis-related protein proteasome subunit α 5 (PSMA5) is increased by vaccenicacid treatment in goat mammary tissue"...
outer cell membrane. Cis-vaccenic and arachidonic acids are found in medium amounts, while C17 and C19 cyclopropane fatty acids are found in very limited...
2012). "Conjugated linoleic acid synthesis-related protein proteasome subunit α 5 (PSMA5) is increased by vaccenicacid treatment in goat mammary tissue"...
C20H38O2 Molar mass 310.51 g/mol Related compounds Related compounds cis-vaccenicacid Except where otherwise noted, data are given for materials in their...
2012). "Conjugated linoleic acid synthesis-related protein proteasome subunit α 5 (PSMA5) is increased by vaccenicacid treatment in goat mammary tissue"...
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