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{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447321268
| verifiedrevid = 447321268
| Name = Rumenic acid
| Name = Rumenic acid
Line 6: Line 7:
| ImageSize = 200px
| ImageSize = 200px
| ImageName = Rumenic acid
| ImageName = Rumenic acid
| IUPACName = (9''Z'',11''E'')-octadeca-9,11-dienoic acid
| PIN = (9''Z'',11''E'')-Octadeca-9,11-dienoic acid
| OtherNames = Bovinic acid; C9-T11 acid
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 54739-30-9
| CASNo = 2540-56-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 46JZW3MR59
| SMILES = CCCCCC\C=C/C=C/CCCCCCCC(=O)O
| SMILES = CCCCCC\C=C/C=C/CCCCCCCC(=O)O
| PubChem = 5280644
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444245
| 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-
| InChIKey = JBYXPOFIGCOSSB-GOJKSUSPBK
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| 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-
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = JBYXPOFIGCOSSB-GOJKSUSPSA-N
| RTECS =
| MeSHName =
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 32798
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C04056
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| Formula = C<sub>18</sub>H<sub>32</sub>O<sub>2</sub>
| C=18|H=32|O=2
| MolarMass = 280.445 g/mol
| Density =
| Density =
| MeltingPt =
| MeltingPt =
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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 an [[Essential fatty acid#Nomenclature and terminology|omega-7]] [[trans fat]]. Its lipid shorthand name is cis-9, trans-11 18:2 acid.
'''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
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 |pmid=9727617 |doi=10.1007/s11745-998-0279-6}}</ref> It is formed along with [[vaccenic acid]] by biohydrogenation of dietary [[polyunsaturated fatty acid]]s in the [[rumen]].<ref name=Destaillats>{{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
|author=F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida}}</ref>
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
| url=http://www.cyberlipid.org/fa/acid0003.htm
| url=http://www.cyberlipid.org/fa/acid0003.htm
| title= Polyenoic Fatty Acids
| title= Polyenoic Fatty Acids
| author=Cyberlipid| accessdate=2007-01-17}}</ref>
| author=Cyberlipid| accessdate=2007-01-17}}</ref>


==Biosynthesis and biotransformations==
==Biological properties==
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]]
:{{main|Conjugated linoleic acid}}

Laboratory studies indicate that rumenic acid shows [[anticarcinogen]]ic properties.<ref name=lock>{{cite journal
==Further reading==
|url =http://jn.nutrition.org/cgi/content/abstract/134/10/2698| journal=J Nutr|volume=134|pages=2698–704
{{cite journal
|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
⚫
|journal= [[Journal of Dairy Science]]|volume=88|issue=449|year=2005
|author= Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C.|accessdate=2007-01-15
⚫
|title=Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats
|pmid= 15465769
|author=F. Destaillats
|issue =10
|author2=E. Buyukpamukcu
|date = October 1, 2004 }}</ref>
|author3=P.-A. Golay
|author4=F. Dionisi
|author5=F. Giuffrida
|name-list-style=amp
|doi= 10.3168/jds.S0022-0302(05)72705-3
|page= 449 |pmid=15653508|doi-access=free
}}


==References==
==References==
{{Reflist}}
{{Reflist}}

{{Fatty acids}}


{{DEFAULTSORT:Rumenic Acid}}
{{DEFAULTSORT:Rumenic Acid}}
[[Category:Fatty acids]]
[[Category:Fatty acids]]
[[Category:Alkenoic acids]]

Latest revision as of 18:53, 12 August 2023

Rumenic acid
Rumenic acid
Names
Preferred IUPAC name
(9Z,11E)-Octadeca-9,11-dienoic acid
Other names
Bovinic acid; C9-T11 acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • 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- ☒N
    Key: JBYXPOFIGCOSSB-GOJKSUSPSA-N ☒N
  • 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-
    Key: JBYXPOFIGCOSSB-GOJKSUSPBK
  • CCCCCC\C=C/C=C/CCCCCCCC(=O)O
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).
☒N verify (what is checkY☒N ?)

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]
  1. ^ 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.
  2. ^ Cyberlipid. "Polyenoic Fatty Acids". Retrieved 2007-01-17.
  3. ^ 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.
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