A pentacyclic triterpenoid with diverse biological activities
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Uvaol

Item No. 33915

Technical Information
Formal Name
urs-12-ene-3β,28-diol
CAS Number
545-46-0
Synonyms
  • NSC 159627
Molecular Formula
C30H50O2
Formula Weight
Purity
≥95%
A solid
Chloroform: 5 mg/mlEthanol: Slightly soluble
SMILES
C[C@@]12C([C@@]3([H])[C@@](CC2)(CC[C@H]([C@@H]3C)C)CO)=CC[C@@]4([H])[C@]1(CC[C@]5([H])[C@@]4(CC[C@@H](C5(C)C)O)C)C
InChi Code
InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3/t19-,20+,22+,23-,24+,25+,27+,28-,29-,30-/m1/s1
InChi Key
XUARCIYIVXVTAE-ZAPOICBTSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Uvaol is a pentacyclic triterpenoid that has been found in olive (O. europaea) leaves and has diverse biological activities.1,2,3,4 It induces cell cycle arrest at the G0/G1 phase and inhibits proliferation of MCF-7 human breast cancer cells in a concentration-dependent manner.2 Uvaol (10 µM) prevents hydrogen peroxide-induced DNA damage in the same cells. It induces relaxation of phenylephrine- or potassium chloride-precontracted aortic rings isolated from spontaneously hypertensive rats when used at a concentration of 100 µM.3 Uvaol (200 and 500 µmol/kg) inhibits ovalbumin-induced bronchoalveolar lavage fluid (BALF) eosinophil infiltration in an ovalbumin-sensitized mouse model of allergic asthma.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Guinda, A., Rada, M., Delgado, T., et alPentacyclic triterpenoids from olive fruit and leaf. J. Agric. Food Chem. 58(17), 9685-9691 (2010).

    2. Allouche, Y., Warleta, F., Campos, M., et alAntioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF-7 human breast cancer cells and their effects on DNA damage. J. Agric. Food Chem. 59(1), 121-130 (2011).

    3. Rodriguez-Rodriguez, R., Perona, J.S., Herrera, M.D., et alTriterpenic compounds from "orujo" olive oil elicit vasorelaxation in aorta from spontaneously hypertensive rats. J. Agric. Food Chem. 54(6), 2096-2102 (2006).

    4. Agra, L.C., Lins, M.P., da Silva Marques, P., et alUvaol attenuates pleuritis and eosinophilic inflammation in ovalbumin-induced allergy in mice. Eur. J. Pharmacol. 780, 232-242 (2016).