A triterpenoid with diverse biological activities
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Isomer(s)
330663-Oxobetulin
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Betulinic Aldehyde

Item No. 27810

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3β-hydroxy-lup-20(29)-en-28-al
CAS Number
13159-28-9
Synonyms
  • Betulinaldehyde
  • NSC 250423
Molecular Formula
C30H48O2
Formula Weight
440.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 2 mg/mlEthanol: 2 mg/ml
λmax
235 nm
SMILES
CC([C@@H]1CC[C@]2(C=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/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/h18,20-25,32H,1,8-17H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
InChi Key
FELCJAPFJOPHSD-ROUWMTJPSA-N
Origin
Plant/White birch bark
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $39

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    5 mg

    $106

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    10 mg

    $193

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    25 mg

    $385

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    Product Description

    Betulinic aldehyde is a triterpenoid that has been found in Z. cambodiana and has diverse biological activities.1,2,3,4 It is active against P. falciparum (IC50 = 6.5 μg/ml) and M. tuberculosis (MIC = 25 μg/ml) in vitro, as well as laboratory and clinical isolates of methicillin-resistant and -sensitive S. aureus (MICs = 128-512 and 8-512 μg/ml, respectively).1,2 Betulinic aldehyde inhibits dengue virus non-structural protein 5 (NS5) RNA-dependent RNA polymerase (IC50 = 6.1 μM) and inhibits dengue virus type 2 replication by 20 and 55% when used at concentrations of 5 and 10 μg/ml, respectively.3 It also inhibits growth of leukemia, melanoma, neuroblastoma, and normal fibroblast cell lines (IC50s = 1.1-4.9, 9.6-10.6, 7.5-8.8, and 18.5 μM, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Suksamrarn, S., Panseeta, P., Kunchanawatta, S., et al. Ceanothane- and lupane-type triterpenes with antiplasmodial and antimycobacterial activities from Ziziphus cambodiana. Chem. Pharm. Bull. (Tokyo) 54(4), 535-537 (2006).

    2. Chung, P.Y., Chung, L.Y., and Navaratnam, P. Potential targets by pentacyclic triterpenoids from Callicarpa farinosa against methicillin-resistant and sensitive Staphylococcus aureus. Fitoterapia 94, 48-54 (2014).

    3. Peyrat, L.-A., Eparvier, V., Eydoux, C., et al. Chemical diversity and antiviral potential in the pantropical Diospyros genus. Fitoterapia 112, 9-15 (2016).

    4. Hata, K., Hori, K., Ogasawara, H., et al. Anti-leukemia activities of Lup-28-al-20(29)-en-3-one, a lupane triterpene. Toxicol. Lett. 143(1), 1-7 (2003).