Acido auricolico

Acido auricolico
Acido auricolico
Acido auricolico
Nome IUPAC
acido (11Z,17Z) 14-idrossicosa-11,17-dienoico
Abbreviazioni
14-OH-20:2Δ11c,17c
Caratteristiche generali
Formula bruta o molecolareC20H36O3
Numero CAS37780-50-0
PubChem73242169
SMILES
CCC=CCCC(CC=CCCCCCCCCCC(=O)O)O
Indicazioni di sicurezza
Modifica dati su Wikidata · Manuale

L'acido auricolico è un acido grasso lineare composto da 20 atomi di carbonio, con 2 doppi legami in posizione 11=12 e 17=18 e un ossidrile -OH in posizione 14.

La sua notazione delta: 14-OH-20:2Δ11c,17c

con formula di struttura: 

CH3-CH2-CH=CH-(CH2)2-CH-CH2-CH=CH-(CH2)9-COOH.
                     |
                     OH

Il suo nome IUPAC è acido (11Z,17Z) 14-idrossicosa-11,17-dienoico.

Fu isolato per la prima volta nel 1937 dai ricercatori Kleiman, Spencer, Earle, Nieschlag, Barclay [1] nell'olio dei semi di Lesquerella auriculata, da cui ha preso il nome comune. Nell'olio di lesquerella auricolata e lesquerella densiflora la concentrazione di acido auricolico è compresa tra il 30% ed il 40% del totale degli acidi grassi.[2] Si trova assieme all'acido lesquerolico, R-14-OH-20:1Δ11c anche nell'olio di semi della Lesquerella fendleri(≈3%) e di alcune specie Physaria della famiglia Brassicaceae.[2][3]

L'alta concentrazione di acidi grassi idrossilati comporta la possibilità di formare gliceridi atipici, come trigliceridi che contengono più di 3 gruppi acilici.[1]

Note

  1. ^ a b 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.
  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.

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