Docosapentaenoic acid: Difference between revisions
→Nutrition: Added information on seal oil, cited |
Created an infobox |
||
Line 1: | Line 1: | ||
{{chembox |
|||
| Watchedfields = changed |
|||
| verifiedrevid = 477000690 |
|||
| Name = Eicosapentaenoic acid |
|||
| IUPACName = (7''Z’',10''Z'',13''Z'',16''Z'',19''Z'’)-docosa-7,10,13,16,19-pentaenoic acid |
|||
| Section1 = {{Chembox Identifiers |
|||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|||
| ChemSpiderID = 4942831 |
|||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|||
}} |
|||
| Section2 = {{Chembox Properties |
|||
| Formula = C<sub>22</sub>H<sub>34</sub>O<sub>2</sub> |
|||
| MolarMass = 330.50416 g/mol |
|||
}} |
|||
}} |
|||
'''Docosapentaenoic acid''' designates any straight chain 22:5 [[fatty acid]]. |
'''Docosapentaenoic acid''' designates any straight chain 22:5 [[fatty acid]]. |
||
Revision as of 15:23, 29 April 2015
Names | |
---|---|
IUPAC name
(7Z’',10Z,13Z,16Z,19Z'’)-docosa-7,10,13,16,19-pentaenoic acid
| |
Identifiers | |
ChemSpider | |
Properties | |
C22H34O2 | |
Molar mass | 330.50416 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Docosapentaenoic acid designates any straight chain 22:5 fatty acid.
Isomers
- See essential fatty acid#nomenclature for nomenclature.
all-cis-4,7,10,13,16-docosapentaenoic acid (osbond acid)
![](http://upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Osbond_acid.png/400px-Osbond_acid.png)
all-cis-4,7,10,13,16-docosapentaenoic acid is an ω-6 fatty acid with the trivial name osbond acid. It is formed by an elongation and desaturation of arachidonic acid 20:4 ω-6.
all-cis-7,10,13,16,19-docosapentaenoic acid (clupanodonic acid)
![](http://upload.wikimedia.org/wikipedia/commons/thumb/6/68/DPAnumbering.png/400px-DPAnumbering.png)
all-cis-7,10,13,16,19-docosapentaenoic acid is an ω-3 fatty acid with the trivial name clupanodonic acid, commonly called DPA. It is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source.[1]
Nutrition
Docosapentaeonic acid (DPA) is an omega-3 fatty acid that is structurally similar to EPA with two more carbon chain units. Many chronic diseases have an inflammatory component, and studies indicate that DPA has crucial anti-inflammatory properties. [2]
Dietary sources
These are the top five sources for DPA according to the USDA Agricultural Research Service: [3]
- Fish oil, menhaden .668 22:5 n-3 (DPA) (g) Per Measure
- Fish oil, salmon .407 22:5 n-3 (DPA) (g) Per Measure
- Salmon, red (sockeye), filets with skin, smoked (Alaska Native) 0.335 22:5 n-3 (DPA) (g) Per Measure
- Fish, salmon, Atlantic, farmed, raw .334 22:5 n-3 (DPA) (g) Per Measure
- Beef, variety meats and by-products, brain, cooked, simmered 22:5 n-3 (DPA) (g) Per Measure
Seal oil is also a major source of DPA. DPA represents approximately 5% by weight of the total seal oil. [4]
Docosapentaenoic acid deficiency
In mammals, clupanodonic acid (ω-3 fatty acid) deficiency is accompanied by an increase of the osbond acid (ω-6 fatty acid) isomer; the Osbond/DHA ratio is thus a marker of dietary DHA sufficiency.[5] However, this usage has been questioned.[6]
References
- ^ Ho, Cosmos. "The Studies of Seal Oil". The Benefits of Omega 3 Fatty Acids found In Seal Oil, as Opposed to Fish and Flaxseed Oils. Newfoundland Health Foods. Retrieved December 24, 2013.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Byelashov, Alex. “DPA: An Up-and-Coming Fatty Acid.” Supply Side Insights. 2013
- ^ “DPA Nutrient List.” National Nutrient Database for Standard Reference Release 27.
- ^ “What types of omega-3 fatty acids are in seal oil?” DHA/EPA Omega-3 Institute. 2013.
- ^ Hornstra, Gerard; Al, Monique D.M.; Houwelingen, Adriana C.v.; Foreman-van Drongelen, Magritha M.H.P. (1995). "Essential fatty acids in pregnancy and early human development". Eur. J. Obstet. Gynecol. Reprod. Biol. 61 (1): 57–62. doi:10.1016/0028-2243(95)02153-J. ISSN 0301-2115. Retrieved December 24, 2013.
- ^ Innis, Sheila M; Vaghri, Ziba; King, D Janette (September 2004). "n−6 Docosapentaenoic acid is not a predictor of low docosahexaenoic acid status in Canadian preschool children1,2,3". Am. J. Clin. Nutr. 80 (3): 768–773.
See also