A triterpenoid with diverse biological activities
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Betulinic Acid methyl ester

Item No. 30066

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β)-3-hydroxy-Lup-20(29)-en-28-oic acid, methyl ester
CAS Number
2259-06-5
Synonyms
  • Methyl Betulinate
  • NSC 152532
Molecular Formula
C31H50O3
Formula Weight
470.7
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
CC([C@@H]1CC[C@]2(C(OC)=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/C31H50O3/c1-19(2)20-11-16-31(26(33)34-8)18-17-29(6)21(25(20)31)9-10-23-28(5)14-13-24(32)27(3,4)22(28)12-15-30(23,29)7/h20-25,32H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,28-,29+,30+,31-/m0/s1
InChi Key
XNZIMRUZBOZIBC-JVRMVBBZSA-N
Origin
Plant/Akania bidwillii
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $169

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    5 mg

    $502

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    Product Description

    Betulinic acid methyl ester is a lupane-type triterpenoid and an esterified version of betulinic acid (Item No. 11686) that has been found in Helicteres hirsuta and has diverse biological activities.1,2,3,4,5 It inhibits HIV-1 reverse transcriptase (IC50 = 11 μM).1 Betulinic acid methyl ester is active against L. braziliensis and T. cruzi (IC50s = 69.9 and 93.3 μM, respectively).2 It induces melanogenesis in (EC50 = 2.5 μM) and inhibits the growth of B16 2F2 melanoma cells in vitro (IC50 = 4.9 μM).3 Betulinic acid methyl ester is cytotoxic to SK-LU-1, HepG2, HeLa, SK-MEL-2, and AGS cells (IC50s = 60.84, 77.43, 80.17, 66.17, and 69.94 μg/ml, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Akihisa, T., Ogihara, J., Kato, J., et al. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids 36(5), 507-512 (2001).

    2. Domínguez-Carmona, D.B., Escalante-Erosa, F., García-Sosa, K., et al. Antiprotozoal activity of betulinic acid derivatives. Phytomedicine 17(5), 379-382 (2010).

    3. Hata, K., Hori, K., and Takahashi, S. Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line. J. Nat. Prod. 65(5), 645-648 (2002).

    4. Quang, D.N., Pham, C.T., Le, L.T.K., et al. Cytotoxic constituents from Helicteres hirsuta collected in Vietnam. Nat. Prod. Res. 34(4), 585-589 (2020).

    5. Eyong, K.O., Bairy, G., Eno, A.A., et al. Triterpenoids from the stem bark of Vitellaria paradoxa (Sapotaceae) and derived esters exhibit cytotoxicity against a breast cancer cell line. Med. Chem. Res. 27(1), 268-277 (2017).