Docosapentaenoic acid

Structural formula
	Figure (7 Z , 10 Z , 13 Z , 16 Z , 19 Z ) -docosapentaenoic acid
General
Surname	Docosapentaenoic acid
other names	n-3-DPA (omega-3-docosapentaenoic acid); (7 Z , 10 Z , 13 Z , 16 Z , 19 Z ) -Docosa-7,10,13,16,19-pentanoic acid ( IUPAC ); 22: 5 (ω − 3) ( lipid name ); ( Clupanodonic acid ) ( obsolete ); ( Clupadonic acid ) ( obsolete );
Molecular formula	C 22 H 34 O 2
External identifiers / databases
PubChem	5497182
Wikidata	Q17177300
properties
Molar mass	330.51 g mol −1
Physical state	liquid
density	0.92 (20 ° C)
Melting point	below −78 ° C
Refractive index	1.4928 (20 ° C)
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Docosapentaenoic acid (DPA) is a long-chain, unsaturated fatty acid . The five double bonds are each separated by a methylene group . Polyenoic acid is therefore one of the isolenic acids.

Isomers

The docosapentaenoic acids can differ in the position of the double bonds in the chain and their configuration ( cis / trans isomerism ).

Two isomers occur biologically, which are always cis -configured:

Docosa-7,10,13,16,19-pentaenoic acid, an omega-3 fatty acid , is an intermediate product in the formation of docosahexaenoic acid from eicosapentaenoic acid . It comes as glycerol - ester in fish, fish oil , cod liver oil , meat and algae , as well as in turtle oil and eggs oil present in small amounts.
Docosa-4,7,10,13,16-pentaenoic acid is one of the omega-6 fatty acids and is a constitutional isomer . This is formed from arachidonic acid through elongation and desaturation and is known as osbondic acid .

To avoid confusion, the isomers are often referred to as n-3-DPA and n-6-DPA .

Docosapentaenoic acid with the configuration (4 Z , 8 Z , 12 Z , 15 Z , 19 Z ) was also mentioned earlier in the literature, but the existence of this configuration could not be proven.

Obsolete names

The name clupanodonic acid (or also clupandonic acid ), which is frequently used in the literature, should no longer be used because it is now ascribed to docosahexaenoic acid .

Individual evidence

^ ^A ^b ^c John W. Blunt, Murray HG Munro: Dictionary of Marine Natural Products. Chapman & Hall, 2008, ISBN 978-08493-8216-1 , pp. 701 f.
^ ^A ^b ^c Burkhard Fugmann, Susanne Lang-Fugmann, Wolfgang Steglich: RÖMPP Encyclopedia Natural Products. Thieme, 2000, ISBN 3-13-117711-X , p. 143.
↑ H. Gnamm, K. Grafe et al. a .: Handbook of Gerbereichemie und Lederfabrikation. Third volume: Das Leder , 1st part, Springer, 1936, ISBN 978-3-7091-2211-2 (reprint), p. 328.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ Robert G. Ackman: Marine Biogenic Lipids, Fats and Oils. Vol. 1, CRC Press, 1989, ISBN 0-8493-4889-7 , p. 104.
↑ HM Rauen: Biochemical Pocket Book. 2nd edition, Springer, 1964, ISBN 978-3-642-85768-3 (reprint), p. 232.

[Blunt-1] A ^b ^c John W. Blunt, Murray HG Munro: Dictionary of Marine Natural Products. Chapman & Hall, 2008, ISBN 978-08493-8216-1 , pp. 701 f.

[Röm-2] A ^b ^c Burkhard Fugmann, Susanne Lang-Fugmann, Wolfgang Steglich: RÖMPP Encyclopedia Natural Products. Thieme, 2000, ISBN 3-13-117711-X , p. 143.

[3] H. Gnamm, K. Grafe et al. a .: Handbook of Gerbereichemie und Lederfabrikation. Third volume: Das Leder , 1st part, Springer, 1936, ISBN 978-3-7091-2211-2 (reprint), p. 328.

[NV-4] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[5] Robert G. Ackman: Marine Biogenic Lipids, Fats and Oils. Vol. 1, CRC Press, 1989, ISBN 0-8493-4889-7 , p. 104.

[6] HM Rauen: Biochemical Pocket Book. 2nd edition, Springer, 1964, ISBN 978-3-642-85768-3 (reprint), p. 232.