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Oleanolic Acid

Oleanolic Acid

Product ID O4417
Cas No. 508-02-1
Purity ≥98%
Product Unit SizeCostQuantityStock
100 mg $82.70 In stock
500 mg $165.40 In stock
1 g $275.60 In stock
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  • Product Info
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  • Downloads
  • References
  • Description
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Description

Oleanolic acid is a triterpenoid originally found in Vigna angularis and Trigonella foenum-graecum. Oleanolic acid exhibits anticancer, anti-inflammatory, anti-allergic, anti-resorptive, and anti-osteoporotic activities. In hypertrophic scar fibroblasts, oleanolic acid induces mitochondria-dependent apoptosis through the activation of p38 MAPK and JNK and increases in caspase expression. In melanoma cells, oleanolic acid decreases cell viability by inducing caspase 3-mediated apoptosis and inhibiting activity of EGFR. Additionally, in animal models, this compound inhibits eosinophil infiltration, airway inflammation, and production of IL-5, IL-13, IL-17, and IgE; this is through to be mediated by upregulation of Foxp3 and downregulation of GATA-3 and RORγt. In bone marrow macrophages, oleanolic acid inhibits RANKL-induced osteoclast differentiation and mature osteoclast differentiation; it also inhibits LPS-induced bone erosion in animal models.

Product Info

Cas No.

508-02-1

Purity

≥98%

Formula

C30H48O3

Formula Wt.

456.71

IUPAC Name

(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 InChI: 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

Synonym

Astrantiagenin C, Caryophyllin, Giganteumgenin C, Oleanic acid, Virgaureagenin B

Melting Point

310°C

Solubility

Soluble in ether, acetone, chloroform or ethanol. Insoluble in water.

Appearance

White Crystal Powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

O4417 MSDS PDF

Info Sheet

O4417 Info Sheet PDF

References

Chen JY, Zhang L, Zhang H, et al. Triggering of p38 MAPK and JNK Signaling is Important for Oleanolic Acid-Induced Apoptosis via the Mitochondrial Death Pathway in Hypertrophic Scar Fibroblasts. Phytother Res. 2014 Apr 6. [Epub ahead of print]. PMID: 24706573.

Ghosh S, Bishayee K, Khuda-Bukhsh AR. Oleanolic acid isolated from ethanolic extract of Phytolacca decandra induces apoptosis in A375 skin melanoma cells: drug-DNA interaction and signaling cascade. J Integr Med. 2014 Mar;12(2):102-14.PMID: 24666676.

Kim JY, Cheon YH, Oh HM, et al. Oleanolic acid acetate inhibits osteoclast differentiation by downregulating PLCγ2-Ca(2+)-NFATc1 signaling, and suppresses bone loss in mice. Bone. 2014 Mar;60:104-11. PMID: 24361669.

Kim SH, Hong JH, Lee YC. Oleanolic acid suppresses ovalbumin-induced airway inflammation and Th2-mediated allergic asthma by modulating the transcription factors T-bet, GATA-3, RORγt and Foxp3 in asthmatic mice. Int Immunopharmacol. 2014 Feb;18(2):311-24. PMID: 24374304.

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