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{{DISPLAYTITLE:Vaccenic acid}}
{{Infobox fatty acid
| name = Vaccenic acid
| image = Vaccenic acid.png
| image_caption = Structure of vaccenic acid
| IUPAC_name = (11E)-11-Octadecenoic acid
| other_names = trans-11-Octadecenoic acid
| CAS_number = 693-72-1
| molecular_formula = C₁₈H₃₄O₂
| molar_mass = 282.46 g/mol
}}


== Introduction ==
'''Vaccenic acid''' is a naturally occurring [[trans fatty acid]] found in the fat of ruminants and in dairy products. It is an isomer of [[oleic acid]] and is classified as a [[monounsaturated fatty acid]] (MUFA). The name "vaccenic" is derived from the Latin word "vacca," meaning cow, reflecting its presence in cow's milk.


(E)-Octadec-11-enoic acid. It is a naturally occurring trans-[[fatty acid]] found in the fat of [[ruminant]]s and in [[dairy product]]s such as [[milk]], [[butter]], and [[yogurt]].<ref>[http://www.latimes.com/features/health/la-he-eat19-2008may19,0,846200.story Natural trans fats may be good for you.] May 19, 2008</ref>  It is also the predominant fatty acid comprising [[trans fat]] in human milk.<ref>Precht, D and J.Molkentin C18:1, C18:2, and C8:3 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 1999 43(4) 233-244</ref><ref>Friesen, R, and S.M. Innis, Trans Fatty acids in Human milk in Canada declined with the introduction of trans fat food labeling, J. Nut 2006, 136 2558-2561</ref>
== Chemical Structure ==
Vaccenic acid is an 18-carbon fatty acid with one double bond in the trans configuration at the 11th carbon position, denoted as trans-11-octadecenoic acid. Its chemical formula is C₁₈H₃₄O₂, and it has a molar mass of 282.46 g/mol. The presence of the trans double bond gives it a linear structure, distinguishing it from its cis isomer, [[cis-vaccenic acid]].


Its [[IUPAC]] name is (''E'')-11-octadecenoic acid, and its lipid shorthand name is 18:1 ''trans''-11. The name was derived from the [[Latin]] ''vacca'' ([[cow]]).<ref name=Destaillats>{{cite journal
== Sources ==
|journal= [[Journal of Dairy Science]]|volume=88|issue=449|year=2005
Vaccenic acid is predominantly found in:
|title=Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats
* [[Dairy products]] such as milk, cheese, and butter.
|author=F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida
* [[Ruminant]] meat, including beef and lamb.
|doi= 10.3168/jds.S0022-0302(05)72705-3
* Certain [[fermented foods]] where bacterial action can produce trans fatty acids.
|pages= 449}}</ref>


Vaccenic acid was discovered in 1928 in [[animal fat]]s and [[butter]].  It is the main ''[[trans fat|trans]]'' fatty acid [[isomer]] present in [[Butterfat|milk fat]].<ref name=Destaillats/>
== Biological Role ==
Mammals convert it into [[rumenic acid]], a [[conjugated linoleic acid]],<ref name=Bauman>{{cite web
Vaccenic acid is metabolized in the human body to [[rumenic acid]], a type of [[conjugated linoleic acid]] (CLA), which has been studied for its potential health benefits. The conversion is facilitated by the enzyme [[delta-9 desaturase]].
|url =http://www.ansci.cornell.edu/bauman/human_health/index.htm
|title=cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat
|author = Bauman, Dale |accessdate=2007-01-15 |archiveurl = http://web.archive.org/web/20060907102559/http://www.ansci.cornell.edu/bauman/human_health/index.htm <!-- Bot retrieved archive --> |archivedate = 2006-09-07}}</ref><ref name=Banni>{{cite journal
|author=Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C
|title=Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland |journal=Nutr Cancer |volume=41
|issue=1–2 |pages=91–7 |year=2001 |pmid=12094634
|doi=10.1207/S15327914NC41-1&2_12}}</ref>
where it shows anticarcinogenic properties.<ref name=lock>{{cite journal
|url =http://jn.nutrition.org/cgi/content/abstract/134/10/2698| journal=J Nutr|volume=134|pages=2698–704
|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
|author= Lock AL,  Corl BA, Barbano DM, Bauman DE,  Ip C.|accessdate=2007-01-15
|pmid=  15465769
|issue =10
|date = October 1, 2004 }}</ref>


Its stereoisomer, '''cis-vaccenic acid''', is an omega-7 fatty acid, is found in [[Sea Buckthorn]] (''Hippophae rhamnoides'') oil.<ref name=sofa>{{cite web|url =http://www.bagkf.de/sofa/ |author= Federal Research Centre for Nutrition and Food - Institute for Lipid Research|title=Seed Oil Fatty Acids Database}}</ref>  Its [[IUPAC]] name is (''Z'')-11-octadecenoic acid, and its lipid shorthand name is 18:1 ''cis''-11.
== Health Implications ==
The health effects of vaccenic acid are a subject of ongoing research. Some studies suggest that it may have beneficial effects, such as:
* Potential anti-carcinogenic properties due to its conversion to rumenic acid.
* Possible positive effects on [[lipid metabolism]] and [[insulin sensitivity]].


==Health==
However, as a trans fatty acid, there is also concern about its impact on [[cardiovascular health]], although naturally occurring trans fats like vaccenic acid may not have the same negative effects as industrial trans fats.
A 2008 study at the [[University of Alberta]] suggests that vaccenic acid feeding in rats over 16 weeks resulted in lowered total [[cholesterol]], lowered [[Low-density lipoprotein|LDL]] cholesterol and lower [[triglyceride]] levels. The researchers are preparing to conduct further research, including human clinical trials.<ref>AFNS. [http://www.ales.ualberta.ca/afns/news.cfm?story=75846 Alberta natural trans fat research earns global recognition]. April 2, 2008.</ref>


Vaccenic acid is also found in human [[orbitofrontal cortex]] of patients with [[bipolar disorder]] and [[schizophrenia]].<ref>{{cite journal | journal = Schizophr Res | year = 2007 | volume = 91 | issue = 1–3 | pages = 37–50 | doi = 10.1016/j.schres.2006.11.027 | pmid = 17236749 | last1 = McNamara | first1 = RK | last2 = Jandacek | first2 = R | last3 = Rider | first3 = T | last4 = Tso | first4 = P | last5 = Hahn | first5 = CG | last6 = Richtand | first6 = NM | last7 = Stanford | first7 = KE | title = Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications | pmc = 1853256}}</ref><ref>{{cite journal | journal = Psychiatry Research | volume = 160 | year = 2008 | pages = 285–299 | doi = 10.1016/j.psychres.2007.08.021 | pmid = 18715653 | last1 = McNamara | first1 = RK | last2 = Jandacek | first2 = R | last3 = Rider | first3 = T | last4 = Tso | first4 = P | last5 = Stanford | first5 = KE | last6 = Hahn | first6 = CG | last7 = Richtand | first7 = NM | title = Deficits in docosahexaenoic acid and associated elevations in the metabolism of arachidonic acid and saturated fatty acids in the postmortem orbitofrontal cortex of patients with bipolar disorder | issue = 3 | pmc = 2620106}}</ref>
== Metabolism ==
In humans, vaccenic acid is absorbed in the intestine and incorporated into [[lipoproteins]]. It can be oxidized for energy or stored in adipose tissue. The conversion to rumenic acid occurs primarily in the liver.


Oxidation of [[Fatty acid|omega-7 unsaturated fatty acids]] on the skin surface, such as [[palmitoleic acid]] and vaccenic acid, may be the cause of the phenomenon commonly known as [[2-Nonenal|old person smell]].<ref>{{cite journal | author = S. Haze, Y. Gozu, S. Nakamura, Y. Kohno, K. Sawano, H. Ohta and K. Yamazaki | title = 2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging | year = 2001 | journal = [[Journal of Investigative Dermatology]] | volume = 116 | issue = 4 | pages = 520–524 | doi = 10.1046/j.0022-202x.2001.01287.x | pmid = 11286617}}</ref>
== Research ==
Ongoing research is exploring the role of vaccenic acid in:
* [[Chronic disease]] prevention, particularly in relation to [[cancer]] and [[cardiovascular disease]].
* Its impact on [[gut microbiota]] and overall [[digestive health]].


==References==
== Conclusion ==
{{reflist}}
Vaccenic acid is a significant component of the diet in populations consuming high amounts of dairy and ruminant meat. While its health effects are not fully understood, it represents an interesting area of study due to its unique properties and potential benefits.
 
== See Also ==
* [[Trans fatty acid]]
* [[Monounsaturated fatty acid]]
* [[Conjugated linoleic acid]]
 
== References ==
{{Reflist}}
 
== External Links ==
* [Link to a relevant scientific article or database]


[[Category:Fatty acids]]
[[Category:Fatty acids]]
[[Category:Animal fats]]
[[Category:Trans fatty acids]]
[[Category:Dairy products]]
[[Category:Monounsaturated fatty acids]]
{{Fatty acids}}{{food}} {{adapted}}
[[Category:Nutrition]]
== Vaccenic_acid ==
<gallery>
File:Trans-vaccenic_acid.svg|Trans-vaccenic acid
File:Vaccenic-acid-3D-balls.png|Vaccenic acid 3D balls
</gallery>

Latest revision as of 11:33, 25 February 2025

Template:Infobox fatty acid

Introduction[edit]

Vaccenic acid is a naturally occurring trans fatty acid found in the fat of ruminants and in dairy products. It is an isomer of oleic acid and is classified as a monounsaturated fatty acid (MUFA). The name "vaccenic" is derived from the Latin word "vacca," meaning cow, reflecting its presence in cow's milk.

Chemical Structure[edit]

Vaccenic acid is an 18-carbon fatty acid with one double bond in the trans configuration at the 11th carbon position, denoted as trans-11-octadecenoic acid. Its chemical formula is C₁₈H₃₄O₂, and it has a molar mass of 282.46 g/mol. The presence of the trans double bond gives it a linear structure, distinguishing it from its cis isomer, cis-vaccenic acid.

Sources[edit]

Vaccenic acid is predominantly found in:

Biological Role[edit]

Vaccenic acid is metabolized in the human body to rumenic acid, a type of conjugated linoleic acid (CLA), which has been studied for its potential health benefits. The conversion is facilitated by the enzyme delta-9 desaturase.

Health Implications[edit]

The health effects of vaccenic acid are a subject of ongoing research. Some studies suggest that it may have beneficial effects, such as:

However, as a trans fatty acid, there is also concern about its impact on cardiovascular health, although naturally occurring trans fats like vaccenic acid may not have the same negative effects as industrial trans fats.

Metabolism[edit]

In humans, vaccenic acid is absorbed in the intestine and incorporated into lipoproteins. It can be oxidized for energy or stored in adipose tissue. The conversion to rumenic acid occurs primarily in the liver.

Research[edit]

Ongoing research is exploring the role of vaccenic acid in:

Conclusion[edit]

Vaccenic acid is a significant component of the diet in populations consuming high amounts of dairy and ruminant meat. While its health effects are not fully understood, it represents an interesting area of study due to its unique properties and potential benefits.

See Also[edit]

References[edit]

<references group="" responsive="1"></references>


External Links[edit]

  • [Link to a relevant scientific article or database]

Vaccenic_acid[edit]

  • Trans-vaccenic acid
    Trans-vaccenic acid
  • Vaccenic acid 3D balls
    Vaccenic acid 3D balls
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