A derivative of betulin
Related Products
Isomer(s)
330513-Acetyl Betulinaldehyde
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3-Oxobetulin Acetate

Item No. 33067

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
28-(acetyloxy)-lup-20(29)-en-3-one
CAS Number
136587-07-0
Synonyms
  • 28-O-acetyl-3-Oxobetulin
  • 3-oxo-28-O-Acetylbetulin
Molecular Formula
C32H50O3
Formula Weight
482.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 10 mg/mlEthanol: 25 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(COC(C)=O)CC1
InChi Code
InChI=1S/C32H50O3/c1-20(2)22-11-16-32(19-35-21(3)33)18-17-30(7)23(27(22)32)9-10-25-29(6)14-13-26(34)28(4,5)24(29)12-15-31(25,30)8/h22-25,27H,1,9-19H2,2-8H3/t22-,23+,24-,25+,27+,29-,30+,31+,32+/m0/s1
InChi Key
KONAXQKGWYDUTG-MOFGVCBJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    25 mg

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    Cayman Chemical
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    Product Description

    3-Oxobetulin acetate is a derivative of the cholesterol biosynthesis inhibitor betulin (Item No. 11041).1 It inhibits the growth of P388 murine lymphocytic leukemia cells (EC50 = 0.12 µg/ml), as well as human MCF-7 breast, SF-268 CNS, H460 lung, and KM20L2 colon cancer cells (GI50s = 8, 10.6, 5.2, and 12.7 µg/ml, respectively), but not BxPC-3 pancreas or DU145 prostate cancer cells (GI50s = >10 µg/ml for both).2 3-Oxobetulin acetate inhibits replication of X4 tropic recombinant HIV (NL4.3-Ren) in MT-2 lymphoblastoid cells (IC50 = 13.4 µM).3 It is also active against L. donovani amastigotes when used at a concentration of 50 µM.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Alakurtti, S., Bergström, P., Sacerdoti-Sierra, N., et al. Anti-leishmanial activity of betulin derivatives. J. Antibiot. (Tokyo) 63(3), 123-126 (2010).

    2. Pettit, G.R., Melody, N., Hempenstall, F., et al. Antineoplastic agents. 595. Structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimer. J. Nat. Prod. 77(4), 863-872 (2014).

    3. 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).