Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H32O2 |
| Molecular Weight | 280.4455 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCC\C=C\C=C/CCCCCCCC(O)=O
InChI
InChIKey=JBYXPOFIGCOSSB-GOJKSUSPSA-N
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9-
| Molecular Formula | C18H32O2 |
| Molecular Weight | 280.4455 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Optical Activity | NONE |
Rumenic acid is the major conjugated linoleic acid (CLA), probably because of successive desaturation and chain elongation and can be considered as the principal dietary form. In experiments on rodents was shown that rumenic acid possessed the protective effect against colitis, which was associated with the activation of the Nrf2 pathway.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue. | 1999 Jul |
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| Dairy product consumption and the risk of breast cancer. | 2005 Dec |
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| Conjugated linoleic acid in ewe milk fat. | 2005 Nov |
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| New class of linoleic acid metabolites biosynthesized by corn and rice lipoxygenases: suppression of proinflammatory mediator expression via attenuation of MAPK- and Akt-, but not PPARgamma-, dependent pathways in stimulated macrophages. | 2005 Nov 1 |
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| Absorption and metabolism of conjugated alpha-linolenic acid given as free fatty acids or triacylglycerols in rats. | 2006 Jan 20 |
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| Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. | 2006 Jul |
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| Effect of dietary supply of butters rich either in trans-10-18 : 1 or in trans-11-18 : 1 plus cis-9, trans-11-18 : 2 on rabbit adipose tissue and liver lipogenic activities. | 2006 Sep |
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| Influence of organic diet on the amount of conjugated linoleic acids in breast milk of lactating women in the Netherlands. | 2007 Apr |
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| Effects of three different conjugated linoleic acid preparations on insulin signalling, fat oxidation and mitochondrial function in rats fed a high-fat diet. | 2007 Aug |
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| Heterologous expression of linoleic acid isomerase from Propionibacterium acnes and anti-proliferative activity of recombinant trans-10, cis-12 conjugated linoleic acid. | 2007 Aug |
|
| Evaluating the conjugated linoleic acid and trans 18:1 isomers in milk fat of dairy cows fed increasing amounts of sunflower oil and a constant level of fish oil. | 2007 Aug |
|
| Dietary trans 10, cis 12-conjugated linoleic acid reduces the expression of fatty acid oxidation and drug detoxification enzymes in mouse liver. | 2007 Jan |
|
| Adverse effects of conjugated alpha-linolenic acids (CLnA) on lipoprotein profile on experimental atherosclerosis in hamsters. | 2007 Jul |
|
| Antidiabetic effects of cis-9, trans-11-conjugated linoleic acid may be mediated via anti-inflammatory effects in white adipose tissue. | 2007 Mar |
|
| Rumenic acid significantly reduces plasma levels of LDL and small dense LDL cholesterol in hamsters fed a cholesterol- and lipid-enriched semi-purified diet. | 2007 Mar |
|
| Effects of feeding camelina (seeds or meal) on milk fatty acid composition and butter spreadability. | 2007 Nov |
|
| Conjugated linoleic acid (CLA) and obesity. | 2007 Oct |
|
| Isomers of conjugated linoleic acids are synthesized via different mechanisms in ruminal digesta and bacteria. | 2007 Oct |
|
| Bovine milk in human nutrition--a review. | 2007 Sep 25 |
|
| Effect of conjugated linoleic acid, vitamin E and their combination on lipid profiles and blood pressure of Iranian adults with active rheumatoid arthritis. | 2008 |
|
| Ruminant and industrially produced trans fatty acids: health aspects. | 2008 |
|
| Comprehensive analysis of polar and apolar constituents of butter and margarine by nuclear magnetic resonance, reflecting quality and production processes. | 2008 Apr 23 |
|
| Effects of butter naturally enriched with conjugated linoleic acid and vaccenic acid on blood lipids and LDL particle size in growing pigs. | 2008 Aug 29 |
|
| Nonionophore antibiotics do not affect the trans-18:1 and conjugated linoleic acid composition in beef adipose tissue. | 2008 Dec |
|
| Kinetics of ruminal lipolysis of triacylglycerol and biohydrogenation of long-chain fatty acids: new insights from old data. | 2008 Feb |
|
| Fatty acid profile of Canadian dairy products with special attention to the trans-octadecenoic acid and conjugated linoleic acid isomers. | 2008 Jul-Aug |
|
| Physico-chemical modifications of conjugated linoleic acid for ruminal protection and oxidative stability. | 2008 Jun 1 |
|
| Cytotoxic effects of the conjugated linoleic acid isomers t10c12, c9t11-CLA and mixed form on rat hepatic stellate cells and CCl4-induced hepatic fibrosis. | 2008 Mar |
|
| Conjugated linoleic acid content of human plasma. | 2008 Sep 30 |
|
| A novel paradigm of fatty acid beta-oxidation exemplified by the thioesterase-dependent partial degradation of conjugated linoleic acid that fully supports growth of Escherichia coli. | 2008 Sep 9 |
|
| Isomer specificity of conjugated linoleic acid (CLA): 9E,11E-CLA. | 2008 Winter |
|
| Effect of conjugated linoleic acids from beef or industrial hydrogenation on growth and adipose tissue characteristics of rats. | 2009 Apr 22 |
|
| Grazing cows are more efficient than zero-grazed and grass silage-fed cows in milk rumenic acid production. | 2009 Aug |
|
| Factors influencing variation of fatty acid content in ovine milk. | 2009 Aug |
|
| Metabolic fate of fatty acids involved in ruminal biohydrogenation in sheep fed concentrate or herbage with or without tannins. | 2009 Aug |
|
| Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production. | 2009 Aug |
|
| Conjugated Linoleic Acid (CLA) content of meat from three muscles of Massese suckling lambs slaughtered at different weights. | 2009 Feb |
|
| Differences between human subjects in the composition of the faecal bacterial community and faecal metabolism of linoleic acid. | 2009 Feb |
|
| Selective production of cis-9,trans-11 isomer of conjugated linoleic acid from trans-vaccenic acid methyl ester by Delacroixia coronata. | 2009 May |
|
| Conjugated linoleic acids as functional food: an insight into their health benefits. | 2009 Sep 18 |
|
| Lipid profiles and trans fatty acids in serum phospholipids of semi-nomadic Fulani in northern Nigeria. | 2010 Apr |
|
| Short communication: heritability of milk fatty acid composition and stearoyl-CoA desaturase indices in dairy cows. | 2010 Apr |
|
| Effect of grain type and processing method on rumen fermentation and milk rumenic acid production. | 2010 Aug |
|
| trans-fatty acid isomers in adipose tissue have divergent associations with adiposity in humans. | 2010 Aug |
|
| Effects of fish oil and starch added to a diet containing sunflower-seed oil on dairy goat performance, milk fatty acid composition and in vivo delta9-desaturation of [13C]vaccenic acid. | 2010 Aug |
|
| Chemoenzymatic conversion of linoleic acid into conjugated linoleic acid. | 2010 Feb 10 |
|
| Fatty acids and breast cancer: sensitization to treatments and prevention of metastatic re-growth. | 2010 Jan |
|
| A review of fatty acid profiles and antioxidant content in grass-fed and grain-fed beef. | 2010 Mar 10 |
|
| Bovine liver slices combined with an androgen transcriptional activation assay: an in-vitro model to study the metabolism and bioactivity of steroids. | 2010 May |
|
| Influence of diet enriched with conjugated linoleic acids on their distribution in tissues of rats with DMBA induced tumors. | 2010 Nov 2 |
Patents
Sample Use Guides
Rumenic acid was highly metabolized by bovine hepatocytes, especially by the oxidation pathway and by its conversion into conjugated C18:3. Bovine liver slices were incubated for 17 h in a medium containing 0.75 mM of FA mixture and 55 microM of either [1-(14)C] rumenic acid or [1-(14)C] oleic acid at 37 degrees C under an atmosphere of 95% O(2)-5% CO(2). Hepatic oxidation of both FA (> 50% of incorporated FA) led essentially to the production of acid-soluble products and to a lower extent to CO(2) production. Rumenic acid was partly converted into conjugated C18:3. CLA and its conjugated derivatives were mainly esterified into polar lipids (71.7%), whereas oleic acid was preferentially esterified into neutral lipids (59.8%). Rumenic acid secretion as part of VLDL particles was very low and was one-fourth lower than that of oleic acid.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:54:38 UTC 2023
by
admin
on
Fri Dec 15 18:54:38 UTC 2023
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| Record UNII |
46JZW3MR59
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| Record Status |
Validated (UNII)
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| Record Version |
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1839-11-8
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RUMENIC ACID
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32798
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46JZW3MR59
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2540-56-9
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DTXSID1041003
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7886
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C046938
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5280644
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