Ácido oleanólico

 
Ácido oleanólico
Nombre IUPAC
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
General
Fórmula estructural Imagen de la estructura
Fórmula molecular C
30H
48O
3
Identificadores
Número CAS 508-02-1[1]​
ChEBI 37659
ChEMBL 168
ChemSpider 10062
PubChem 10494
UNII 6SMK8R7TGJ
KEGG C17148
O=C(O)[C@@]54[C@H](/C3=C/C[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC4)CC(C)(C)CC5
InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1
Key: MIJYXULNPSFWEK-GTOFXWBISA-N
Propiedades físicas
Apariencia blanco
Masa molar 456,7 g/mol
Punto de fusión 300 K (27 °C)
Valores en el SI y en condiciones estándar
(25 ℃ y 1 atm), salvo que se indique lo contrario.
[editar datos en Wikidata]

El ácido oleanólico[2]​ es un ácido triterpénico que se encuentra de forma natural en numerosas plantas entre las que se cuenta el olivo (olea europea) y la vid. Es uno de los componentes del aceite de oliva, las aceitunas y las uvas. Su fórmula es 3-betahidroxi-28-carboxioleanano.[3]​

Se le han atribuido numerosas propiedades beneficiosas para la salud, por lo cual se están realizando estudios en diferentes países para comprobar si su consumo habitual puede constituir un tratamiento eficaz para diferentes enfermedades como la diabetes. Los resultados obtenidos hasta el momento son esperanzadores.[4]​

Producción natural

Se estudió y ha sido aislado de varias plantas, incluyendo Olea europaea[5]​ (hojas, fruto), Rosa woodsii (hojas), Prosopis glandulosa (hojas), Phoradendron juniperinum (toda la planta), Syzygium claviflorum (hojas), Hyptis capitata (toda la planta), Mirabilis jalapa[6]​ y Ternstromia gymnanthera (parte aérea). Otras especies de Syzygium incluyendo Syzygium samarangense.

Referencias

  1. ↑ Número CAS
  2. ↑ Oleanolic acid at Sigma-Aldrich
  3. ↑ Worl Intellectual Property Organization: Nutraceutical composition obtained from natural triterpenes. Consultado el 8/4/2010
  4. ↑ Yoshikawa, Hisashi Matsuda: Antidiabetogenic activity of oleanolic acid glycosides from medicinal foodstuffs, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan. Consultado el 8/4/2010
  5. ↑ HMDB entry for Oleanolic acid
  6. ↑ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract Archivado el 4 de enero de 2014 en Wayback Machine.)

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