A pentacyclic triterpenoid with diverse biological activities
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Oleanolic Acid

Item No. 11726

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3β-hydroxy-olean-12-en-28-oic acid
CAS Number
508-02-1
Synonyms
  • Astrantiagenin C
  • Caryophyllin
  • Giganteumgenin C
  • Gledigenin 1
  • NSC 114945
  • Oleanoic Acid
  • Virgaureagenin B
Molecular Formula
C30H48O3
Formula Weight
456.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH7.2) (1:2): 0.3 mg/mlDMSO: 3 mg/mlEthanol: 5 mg/ml
SMILES
CC1(C)CC[C@]2(C(O)=O)CC[C@@]3(C)[C@]4(C)CC[C@@]5([H])C(C)(C)[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])C1
InChi Code
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
InChi Key
MIJYXULNPSFWEK-GTOFXWBISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Product Description

    Oleanolic acid is a pentacyclic triterpenoid that has been found in O. europaea and has diverse biological activities.1,2,3,4,5 It is active against S. aureus, B. thuringiensis, E. coli, S. enterica, and S. dysenteriae (MICs = 1.9, 1.9, 7.8, 3.9, and 1.9 µg/ml, respectively) and scavenges hydroxyl and superoxide radicals in cell-free assays when used at a concentration of 1 mg/ml. Oleanolic acid is cytotoxic to DU145 prostate and MCF-7 breast cancer cells, as well as U87 glioblastoma cells, with IC50 values of 112.57, 132.29, and 163.6 µg/ml.3 It reduces LPS-induced adherence of THP-1 monocytes to human umbilical vein endothelial cells (HUVECs) in a co-culture model of monocyte-endothelial cell adhesion when used at concentrations ranging from 10 to 50 µM.4 Oleanolic acid (200 µmol/kg) decreases liver necrosis in several mouse models of liver injury, including those induced by acetaminophen (Item No. 10024), carbon tetrachloride (CCl4), or LPS/D-galactosamine.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, X., Ye, X.-l., Liu, R., et al. Antioxidant activities of oleanolic acid in vitro: Possible role of Nrf2 and MAP kinases. Chem. Biol. Interact. 184(3), 328-337 (2010).

    2. Wang, J., Ren, H., Xu, Q.-L., et al. Antibacterial oleanane-type triterpenoids from pericarps of Akebia trifoliata. Food Chem. 168, 623-629 (2015).

    3. Kim, G.-J., Jo, H.-J., Lee, K.-J., et al. Oleanolic acid induces p53-dependent apoptosis via the ERK/JNK/AKT pathway in cancer cell lines in prostatic cancer xenografts in mice. Oncotarget 9(41), 26370-26386 (2018).

    4. Lee, W., Yang, E.-J., Ku, S.-K., et al. Anti-inflammatory effects of oleanolic acid on LPS-induced inflammation in vitro and in vivo. Inflammation 36(1), 94-102 (2013).

    5. Liu, J., Liu, Y., and Klaassen, C.D. Protective effect of oleanolic acid against chemical-induced acute necrotic liver injury in mice. Zhongguo Yao Li Xue Bao 16(2), 97-102 (1995).