A plant triterpenoid similar to bile acids
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Betulinic Acid

Item No. 11686

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3β-hydroxy-lup-20(29)-en-28-oic acid
CAS Number
472-15-1
Synonyms
  • Lupatic Acid
  • NSC 113090
Molecular Formula
C30H48O3
Formula Weight
456.7
Purity
≥97%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.3 mg/mlEthanol: 0.5 mg/ml
SMILES
CC([C@@H]1CC[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[C@]3([H])[C@]21[H])=C
InChi Code
InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
InChi Key
QGJZLNKBHJESQX-FZFNOLFKSA-N
Origin
Plant/Crataeva nurvala Betula alba
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $40

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    100 mg

    $73

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    250 mg

    $143

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    500 mg

    $246

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    Product Description

    Betulinic acid is a natural plant triterpenoid that is structurally related to mammalian bile acids. It is an agonist of the G protein-coupled bile acid receptor TGR5 (EC50 = 1 µM), which might be linked with its ability to alter gene expression and fatty liver development in cells and mice given ethanol.1,2,3 Betulinic acid also reduces NF-κB signaling and expression of microRNA-33 in LPS-treated macrophages, increasing levels of the ATP-binding cassette (ABC) cholesterol transporter ABCA1.4 It also inhibits replication of HIV-1 (IC50 = 1.4 µM) and has cytotoxic effects against cancer cells.3,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Genet, C., Strehle, A., Schmidt, C., et al. Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: Potential impact in diabetes. J. Med. Chem. 53(1), 178-190 (2010).

    2. Wan, Y., Jiang, S., Lian, L.H., et al. Betulinic acid and betulin ameliorate acute ethanol-induced fatty liver via TLR4 and STAT3 in vivo and in vitro. Int. Immunopharmacol. 17(2), 184-190 (2013).

    3. Kashiwada, Y., Hashimoto, F., Cosentino, L.M., et al. Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J. Med. Chem. 39(5), 1016-1017 (1996).

    4. Zhao, G.J., Tang, S.L., Lv, Y.C., et al. Antagonism of betulinic acid on LPS-mediated inhibition of ABCA1 and cholesterol efflux through inhibiting nuclear factor-kappaB signaling pathway and miR-33 expression. PLoS One 8(9), e474782 (2013).

    5. Mullauer, F.B., Kessler, J.H., and Medema, J.P. Betulin is a potent anti-tumor agent that is enhanced by cholesterol. PLoS One 4(4), (2009).