Densipolic acid

Densipolic acid

Names
IUPAC name (9Z,12R,15Z)-12-hydroxyoctadeca-9,15-dienoic acid
Other names 12R-HODE
Identifiers
CAS Number	7121-47-3  N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:165769
ChemSpider	4472256
PubChem CID	5312831
InChI InChI=1S/C18H32O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h3-4,9,12,17,19H,2,5-8,10-11,13-16H2,1H3,(H,20,21)/b4-3-,12-9-/t17-/m1/s1 Key: OKIDIWHWTIMACU-MNEPGTOVSA-N
SMILES CCC=CCCC(CC=CCCCCCCCC(=O)O)O
Properties
Chemical formula	C18H32O3
Molar mass	296.451 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Densipolic acid is a linear fatty acid composed of 18 carbon atoms, with two double bonds in the positions 9=10 and 15=16 and a hydroxyl-OH in the position 12. Although the compound has no nutritional relevance, densipolic acid is an Omega-3 acid.

Discovery

The acid was initially isolated C. R. Smith and colleagues in 1962 from the seed oil of the Lesquerella densipila plant, from which it takes its name. ^{[1] [2]}

The acid is typically found together with other hydroxylated fatty acids (lesquerolic, auricolic, ricinoleic, etc.) in the seed oil of other Lesquerella species (lescurii, perforata, stonensis, lyrata, etc.) and some Physaria species of the Brassicaceae family. ^[3]

Chemical properties

The biosynthetic pathways of hydroxylated fatty acids in plants have not been fully researched. There is biochemical evidence that an n-3 desaturase, in acids with 18 carbon atoms a Δ15 desaturase, is able to convert ricinoleic acid to densipolic acid. ^{[4] [5] [6]}

In seed oils with high concentrations of hydroxylated fatty acids there is the possibility of forming atypical glycerides, such as triglycerides containing more than three acyl groups. ^[7]

See also

• Bladderpod oil

References

1. Smith, C. R. Jr.; Wilson, T. L.; Bates, R. B.; Scholfield, C. R. (1 September 1962). "Densipolic Acid: a Unique Hydroxydienoid Acid from Lesquerella densipila Seed Oil1a" . The Journal of Organic Chemistry . 27 (9): 3112–3117. doi:10.1021/jo01056a031. ISSN   0022-3263 . Retrieved 4 April 2025.
2. Jenderek, M. M.; Dierig, D. A.; Isbell, T. A. (1 January 2009). "Fatty-acid profile of Lesquerella germplasm in the National Plant Germplasm System collection" . Industrial Crops and Products. 29 (1): 154–164. doi:10.1016/j.indcrop.2008.04.019. ISSN   0926-6690 . Retrieved 4 April 2025.
3. Salywon, Andrew M.; Dierig, David A.; Rebman, Jon P.; de Rodríguez, Diana Jasso (2005). "Evaluation of new Lesquerella and Physaria (Brassicaceae) oilseed germplasm" . American Journal of Botany . 92 (1): 53–62. Bibcode:2005AmJB...92...53S. doi:10.3732/ajb.92.1.53. ISSN   1537-2197. PMID   21652384 . Retrieved 4 April 2025.
4. Engeseth, Nicki; Stymne, Sten (1996). "Desaturation of oxygenated fatty acids in Lesquerella and other oil seeds" . Planta . 198 (2): 238–245. Bibcode:1996Plant.198..238E. doi:10.1007/BF00206249. ISSN   0032-0935. JSTOR   23384263 . Retrieved 4 April 2025.
5. Broun, P.; Somerville, C. (March 1997). "Accumulation of ricinoleic, lesquerolic, and densipolic acids in seeds of transgenic Arabidopsis plants that express a fatty acyl hydroxylase cDNA from castor bean". Plant Physiology . 113 (3): 933–942. doi:10.1104/pp.113.3.933. ISSN   0032-0889. PMC   158213 . PMID   9085577.
6. Applewhite, T. H.; Binder, R. G.; Gaffield, W. (1 January 1965). "The absolute configuration of dimorphecolic, lesquerolic, and densipolic acids" . Chemical Communications (12): 255–256. doi:10.1039/C19650000255. ISSN   0009-241X . Retrieved 4 April 2025.
7. Kleiman, R.; Spencer, G. F.; Earle, F. R.; Nieschlag, H. J.; Barclay, A. S. (1972). "Tetra-acid triglycerides containing a new hydroxy eicosadienoyl moiety inLesquerella auriculata seed oil" . Lipids . 7 (10): 660–665. doi:10.1007/BF02533073. ISSN   1558-9307 . Retrieved 4 April 2025.