A pentacyclic triterpenoid with diverse biological activities
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Isomer(s)
27810Betulinic Aldehyde
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3-Oxobetulin

Item No. 33066

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
28-hydroxy-lup-20(29)-en-3-one
CAS Number
7020-34-0
Synonyms
  • Betulone
Molecular Formula
C30H48O2
Formula Weight
440.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/ml
SMILES
C[C@]1([C@]2([C@]([C@@]3([C@@](C(C)(C(CC3)=O)C)([H])CC2)C)([H])CC4)C)[C@@]4([H])[C@]([C@@H](CC5)C(C)=C)([H])[C@@]5(CO)CC1
InChi Code
InChI=1S/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-23,25,31H,1,8-18H2,2-7H3/t20-,21+,22-,23+,25+,27-,28+,29+,30+/m0/s1
InChi Key
JYDNKGUBLIKNAM-CNRMHUMKSA-N
Origin
Semisynthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    5 mg

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    25 mg

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    Product Description

    3-Oxobetulin is a pentacyclic triterpenoid and derivative of betulinic acid (Item No. 11686) that has been found in I. macropoda and has diverse biological activities.1,2,3 3-Oxobetulin reduces HIV-1 replication in MT-2 cells (IC50 = 4.1 µM) with a 50% cytotoxic concentration (CC50) value of greater than 100 µM.4 It inhibits cadmium-induced cytotoxicity in HepG2 cells in a concentration-dependent manner.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kim, D.K., Nam, I.Y., Kim, J.W., et al. Pentacyclic triterpenoids from Ilex macropoda. Arch. Pharm. Res. 25(5), 617-620 (2002).

    2. Chien, S.-C., Xiao, J.-H., Tseng, Y.-H., et al. Composition and antifungal activity of balsam from Liquidambar formosana Hance. Holzforschung 67(3), 345-351 (2013).

    3. Hiroya, K., Takahashi, T., Miura, N., et al. Synthesis of betulin derivatives and their protective effects against the cytotoxicity of cadmium. Bioorg. Med. Chem. 10(10), 3229-3236 (2002).

    4. Callies, O., Bedoya, L.M., Beltrán, M., et al. Isolation, structural modification, and HIV inhibition of pentacyclic lupane-type triterpenoids from Cassine xylocarpa and Maytenus cuzcoina. J. Nat. Prod. 78(5), 1045-1055 (2015).