Docosapentaenoic acid

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Docosapentaenoic acid
Names
IUPAC name
(7Z’',10Z,13Z,16Z,19Z'’)-docosa-7,10,13,16,19-pentaenoic acid
Identifiers
ChemSpider 4942831 YesY
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).
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Infobox references

Docosapentaenoic acid designates any straight chain 22:5 fatty acid.

Isomers[edit]

See essential fatty acid#nomenclature for nomenclature.

all-cis-4,7,10,13,16-docosapentaenoic acid (osbond acid)[edit]

The chemical structure of osbond acid showing physiological numbering (red) and chemical numbering (blue) conventions.


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)[edit]

The chemical structure of clupanodonic acid showing physiological numbering (red) and chemical numbering (blue) conventions.


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).

Nutrition[edit]

Docosapentaeonic acid (DPA) is an omega-3 fatty acid that is structurally similar to eicosapentaenoic acid (EPA) with two more carbon chain units.[1]

Dietary sources

These are the top five sources for DPA according to the USDA Agricultural Research Service: [2]

  1. Fish oil, menhaden .668 22:5 n-3 (DPA) (g) Per Measure
  2. Fish oil, salmon .407 22:5 n-3 (DPA) (g) Per Measure
  3. Salmon, red (sockeye), filets with skin, smoked (Alaska Native) 0.335 22:5 n-3 (DPA) (g) Per Measure
  4. Fish, salmon, Atlantic, farmed, raw .334 22:5 n-3 (DPA) (g) Per Measure
  5. Beef, variety meats and by-products, brain, cooked, simmered 22:5 n-3 (DPA) (g) Per Measure

Seal meat and human breast milk are rich in DPA.[1]

References[edit]

  1. ^ a b Yazdi PG. A review of the biologic and pharmacologic role of docosapentaenoic acid n-3. Version 2. F1000Res. 2013 Nov 25 [revised 2014 Aug 19];2:256. doi: 10.12688/f1000research.2-256.v2. eCollection 2013. Review. PMID 25232466 PMC 4162505
  2. ^ “DPA Nutrient List.” National Nutrient Database for Standard Reference Release 27.

See also[edit]