Rumenic acid: Difference between revisions
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| Name = Rumenic acid |
| Name = Rumenic acid |
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| ImageFile = Rumenic acid.svg |
| ImageFile = Rumenic acid.svg |
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| ImageSize = 200px |
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| ImageName = |
| ImageName = Rumenic acid |
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| PIN = (9''Z'',11''E'')-Octadeca-9,11-dienoic acid |
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| OtherNames = Bovinic acid; C9-T11 acid |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 2540-56-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 46JZW3MR59 |
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| SMILES = CCCCCC\C=C/C=C/CCCCCCCC(=O)O |
| SMILES = CCCCCC\C=C/C=C/CCCCCCCC(=O)O |
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| PubChem = 5280644 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4444245 |
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| InChI = 1/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- |
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| InChIKey = JBYXPOFIGCOSSB-GOJKSUSPBK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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- |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JBYXPOFIGCOSSB-GOJKSUSPSA-N |
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| RTECS = |
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| MeSHName = |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 32798 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C04056 |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| C=18|H=32|O=2 |
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| MolarMass = [[List of elements by atomic mass|280.445]] g/[[Mole (unit)|mol]] |
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'''Rumenic acid''', also known as '''bovinic acid''', is a [[conjugated linoleic acid]] (CLA) found in the fat of [[ruminant]]s and in [[dairy product]]s. It is |
'''Rumenic acid''', also known as '''bovinic acid''', is a [[conjugated linoleic acid]] (CLA) found in the fat of [[ruminant]]s and in [[dairy product]]s. It is an [[Essential fatty acid#Nomenclature and terminology|omega-7]] [[trans fatty acid]]. Its lipid shorthand name is cis-9, trans-11 18:2 acid. The name was proposed by Kramer ''et al.'' in 1998.<ref name=Kramer>{{cite journal |vauthors=Kramer J, Parodi P, Jensen R, Mossoba M, Yurawecz M, Adlof R |title=Rumenic acid: a proposed common name for the major conjugated linoleic acid isomer found in natural products |journal=Lipids |volume=33 |issue=8 |page=835 |year=1998 |pmid=9727617 |doi=10.1007/s11745-998-0279-6|s2cid=10693714 }}</ref> It can be considered as the principal dietary form, accounting for as much as 85-90% of the total [[Conjugated linoleic acid|CLA]] content in dairy products.<ref name=Cyberlipid>{{cite web |
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The name was proposed by Kramer ''et al'' in 1998.<ref name=Kramer>{{cite journal |author=Kramer J, Parodi P, Jensen R, Mossoba M, Yurawecz M, Adlof R |title=Rumenic acid: a proposed common name for the major conjugated linoleic acid isomer found in natural products |journal=Lipids |volume=33 |issue=8 |pages=835 |year=1998 |id=PMID 9727617}}</ref> It is formed along with [[vaccenic acid]] by biohydrogenation of dietary [[polyunsaturated fatty acid]]s in the [[rumen]].<ref name=Destaillats>{{cite journal |
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|author=F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida |
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|accessdate=2007-01-16}}</ref> |
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It can be considered as the principal dietary form, accounting for as much as 85-90% of the total CLA content in dairy products.<ref name=Cyberlipid>{{cite web |
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| url=http://www.cyberlipid.org/fa/acid0003.htm |
| url=http://www.cyberlipid.org/fa/acid0003.htm |
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| title= Polyenoic Fatty Acids |
| title= Polyenoic Fatty Acids |
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| author=Cyberlipid| accessdate=2007-01-17}}</ref> |
| author=Cyberlipid| accessdate=2007-01-17}}</ref> |
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==Biological properties== |
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==Biosynthesis and biotransformations== |
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:{{see main|Conjugated linoleic acid}} |
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Rumenic acid is produced from [[vaccenic acid]] by the action of unsaturase enzymes.<ref>{{cite journal |doi=10.1093/ajcn/76.3.504|title=Bioconversion of vaccenic acid to conjugated linoleic acid in humans |year=2002 |last1=Turpeinen |first1=Anu M. |last2=Mutanen |first2=Marja |last3=Aro |first3=Antti |last4=Salminen |first4=Irma |last5=Basu |first5=Samar |last6=Palmquist |first6=Donald L. |last7=Griinari |first7=J Mikko |journal=The American Journal of Clinical Nutrition |volume=76 |issue=3 |pages=504–510 |pmid=12197992 |doi-access=free }}</ref> Rumenic acid is converted back to vaccenic acid en route to [[stearic acid]] |
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Laboratory studies indicate that rumenic acid shows [[anticarcinogen]]ic properties.<ref name=lock>{{cite journal |
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|url =http://jn.nutrition.org/cgi/content/abstract/134/10/2698| journal=J Nutr|year=2004 |
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==Further reading== |
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|month=Oct|volume=134(10)|pages=2698-704 |
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{{cite journal |
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|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 |
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|author= Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C.|accessdate=2007-01-15}}</ref> |
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| ⚫ | |||
|author=F. Destaillats |
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|author2=E. Buyukpamukcu |
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|author3=P.-A. Golay |
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|author4=F. Dionisi |
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|author5=F. Giuffrida |
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|name-list-style=amp |
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|doi= 10.3168/jds.S0022-0302(05)72705-3 |
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|page= 449 |pmid=15653508|doi-access=free |
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}} |
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==References== |
==References== |
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{{ |
{{Reflist}} |
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{{Fatty acids}} |
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{{DEFAULTSORT:Rumenic Acid}} |
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[[Category:Fatty acids]] |
[[Category:Fatty acids]] |
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[[Category:Alkenoic acids]] |
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Latest revision as of 18:53, 12 August 2023
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| Names | |
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| Preferred IUPAC name
(9Z,11E)-Octadeca-9,11-dienoic acid | |
| Other names
Bovinic acid; C9-T11 acid
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C18H32O2 | |
| Molar mass | 280.452 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rumenic acid, also known as bovinic acid, is a conjugated linoleic acid (CLA) found in the fat of ruminants and in dairy products. It is an omega-7 trans fatty acid. Its lipid shorthand name is cis-9, trans-11 18:2 acid. The name was proposed by Kramer et al. in 1998.[1] It can be considered as the principal dietary form, accounting for as much as 85-90% of the total CLA content in dairy products.[2]
Biosynthesis and biotransformations
[edit]Rumenic acid is produced from vaccenic acid by the action of unsaturase enzymes.[3] Rumenic acid is converted back to vaccenic acid en route to stearic acid
Further reading
[edit]F. Destaillats; E. Buyukpamukcu; P.-A. Golay; F. Dionisi & F. Giuffrida (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.
References
[edit]- ^ Kramer J, Parodi P, Jensen R, Mossoba M, Yurawecz M, Adlof R (1998). "Rumenic acid: a proposed common name for the major conjugated linoleic acid isomer found in natural products". Lipids. 33 (8): 835. doi:10.1007/s11745-998-0279-6. PMID 9727617. S2CID 10693714.
- ^ Cyberlipid. "Polyenoic Fatty Acids". Retrieved 2007-01-17.
- ^ Turpeinen, Anu M.; Mutanen, Marja; Aro, Antti; Salminen, Irma; Basu, Samar; Palmquist, Donald L.; Griinari, J Mikko (2002). "Bioconversion of vaccenic acid to conjugated linoleic acid in humans". The American Journal of Clinical Nutrition. 76 (3): 504–510. doi:10.1093/ajcn/76.3.504. PMID 12197992.