A pentacyclic triterpenoid
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Betulonaldehyde

Item No. 33042

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-oxo-lup-20(29)-en-28-al
CAS Number
4439-98-9
Synonyms
  • (+)-Betulonal
  • Betulonic Aldehyde
Molecular Formula
C30H46O2
Formula Weight
438.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 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(C=O)CC1
InChi Code
InChI=1S/C30H46O2/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/h18,20-23,25H,1,8-17H2,2-7H3/t20-,21+,22-,23+,25+,27-,28+,29+,30+/m0/s1
InChi Key
MHAVMNJPXLZEIG-CNRMHUMKSA-N
Origin
Semisynthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    10 mg

    $174

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    50 mg

    $734

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    100 mg

    $1,293

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    Product Description

    Betulonaldehyde is a pentacyclic triterpenoid and derivative of the cholesterol biosynthesis inhibitor betulin (Item No. 11041) that has been found in Betula.1 It is active against P. falciparum (IC50 = 3.36 µg/ml) and cytotoxic to NCI H187 lung cancer cells and non-cancerous Vero cells (IC50s = 19.23 and 17.09 µg/ml, respectively).2 Topical application of betulonaldehyde (1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in mice.3 It has also been used a precursor in the semisynthesis of C-2 and C-28 betulonic aldehyde derivatives.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ayers, S., Benkovics, T., Marshall, J., et al. Autoxidation products of betulonaldehyde. J. Nat. Prod. 79(10), 2758-2761 (2016).

    2. Wisetsai, A., Schevenels, F.T., and Lekphrom, R. Chemical constituents and their biological activities from the roots of diospyros filipendula. Nat. Prod. Res. 1-5 (2019).

    3. Yasukawa, K., Yu, S., Yamanouchi, S., et al. Some lupane-type triterpenes inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin. Phytomedicine 1(4), 309-313 (1995).