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Acido densipolico

Acido densipolico
Acido densipcolico
Acido densipcolico
Nome IUPAC
acido (9Z, 12R, 15Z)-12-idrossiottadeca-9,15-dienoico
Abbreviazioni
12-OH-18:2Δ9c,15c
Caratteristiche generali
Formula bruta o molecolareC18H32O3
Numero CAS7121-47-3
PubChem5312831
SMILES
CCC=CCCC(CC=CCCCCCCCC(=O)O)O
Indicazioni di sicurezza

L'acido densipolico è un acido grasso lineare composto da 18 atomi di carbonio, con 2 doppi legami in posizione 9=10 e 15=16 e un ossidrile -OH in posizione 12. Anche se non ha rilevanza nutrizionale, l'acido densipolico è un acido omega-3.

Fu isolato per la prima volta dall'olio di semi della pianta di Lesquerella densipila, da cui ha preso il nome, che ne conteneva tra il 33,7 e il 50% da C.R. Smith e colleghi nel 1962.[1][2]

Tipicamente si trova assieme ad altri acidi grassi idrossilati (acido lesquerolico, auricolico, ricinoleico ecc. ) nell'olio di semi di altre specie Lesquerella (lescurii, perforata, stonensis , lyrata, ecc. ) e alcune specie Physaria della famiglia Brassicaceae.[2][3]

I percorsi di biosintesi degli acidi grassi idrossilati nelle piante non sono stati completamente chiariti.Esistono prove biochimiche che una desaturasi n-3, negli acidi con 18 atomi di carbonio una Δ15 desaturasi, sia in grado di convertire l'acido ricinoleico in acido densipolico.[4][5][6][7][8]

Negli oli di semi con alta concentrazione di acidi grassi idrossilati c'è la possibilità si formino gliceridi atipici, come trigliceridi che contengono più di 3 gruppi acilici.[9]

Note

  1. ^ C. R. Smith, T. L. Wilson e R. B. Bates, Densipolic Acid: a Unique Hydroxydienoid Acid from Lesquerella densipila Seed Oil1a, in The Journal of Organic Chemistry, vol. 27, n. 9, 1º settembre 1962, pp. 3112–3117, DOI:10.1021/jo01056a031. URL consultato il 20 gennaio 2020.
  2. ^ a b (EN) M.M. Jenderek, D.A. Dierig e T.A. Isbell, Fatty-acid profile of Lesquerella germplasm in the National Plant Germplasm System collection, in Industrial Crops and Products, vol. 29, n. 1, 2009-01, pp. 154–164, DOI:10.1016/j.indcrop.2008.04.019. URL consultato il 19 gennaio 2020.
  3. ^ (EN) Andrew M. Salywon, David A. Dierig e Jon P. Rebman, Evaluation of new Lesquerella and Physaria (Brassicaceae) oilseed germplasm, in American Journal of Botany, vol. 92, n. 1, 2005-01, pp. 53–62, DOI:10.3732/ajb.92.1.53. URL consultato il 19 gennaio 2020.
  4. ^ P Broun e C Somerville, Accumulation of ricinoleic, lesquerolic, and densipolic acids in seeds of transgenic Arabidopsis plants that express a fatty acyl hydroxylase cDNA from castor bean., in Plant Physiology, vol. 113, n. 3, 1997-03, pp. 933–942. URL consultato il 20 gennaio 2020.
  5. ^ Nicki Engeseth e Sten Stymne, Desaturation of oxygenated fatty acids in Lesquerella and other oil seeds, in Planta, vol. 198, n. 2, 1996, pp. 238–245. URL consultato il 20 gennaio 2020.
  6. ^ (EN) T. H. Applewhite, R. G. Binder e W. Gaffield, The absolute configuration of dimorphecolic, lesquerolic, and densipolic acids, in Chemical Communications (London), n. 12, 1º gennaio 1965, pp. 255–256, DOI:10.1039/C19650000255. URL consultato il 20 gennaio 2020.
  7. ^ (EN) Hangsik Moon, Mark A. Smith e Ljerka Kunst, A Condensing Enzyme from the Seeds of Lesquerella fendleri That Specifically Elongates Hydroxy Fatty Acids, in Plant Physiology, vol. 127, n. 4, 1º dicembre 2001, pp. 1635–1643, DOI:10.1104/pp.010544. URL consultato il 20 gennaio 2020.
  8. ^ Hou, Kuo, Lanser., 13- Production of hydroxy fatty acid by biocatalysis, in Knothe, Gerhard, Derksen, Johannes T. P. (a cura di), Recent developments in the synthesis of fatty acid derivatives, AOCS Press, 1999, pp. 213-218, ISBN 1-893997-00-6, OCLC 41119199. URL consultato il 20 gennaio 2020.
  9. ^ R. Kleiman, G. F. Spencer e F. R. Earle, Tetra-acid triglycerides containing a new hydroxy eicosadienoyl moiety inLesquerella auriculata seed oil, in Lipids, vol. 7, n. 10, 1972-10, pp. 660–665, DOI:10.1007/bf02533073. URL consultato il 19 gennaio 2020.

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