A lupane triterpenoid with anti-inflammatory and anticancer activities
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Isomer(s)
330493-Acetyl Betulin
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28-Acetylbetulin

Item No. 33052

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β)-28-acetate-lup-20(29)-ene-3,28-diol
CAS Number
27686-35-7
Synonyms
  • 28-acetoxy Betulin
  • 28-O-Acetylbetulin
  • C-28-Acetylbetulin
Molecular Formula
C32H52O3
Formula Weight
484.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: slightly soluble
SMILES
C[C@]1([C@]2([C@]([C@@]3([C@@](C(C)([C@H](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/C32H52O3/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/h22-27,34H,1,9-19H2,2-8H3/t22-,23+,24-,25+,26-,27+,29-,30+,31+,32+/m0/s1
InChi Key
PNDHMMQVMNVWPV-VFUWXHBOSA-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

    $36

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    5 mg

    $153

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    10 mg

    $268

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    25 mg

    $587

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    Product Description

    28-Acetylbetulin is a lupane triterpenoid and derivative of the cholesterol biosynthesis inhibitor betulin (Item No. 11041) that has been found in M. chiapensis and has anti-inflammatory and anticancer activities.1,2 It inhibits LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2; Item No. 14010) production by 55.9 and 69.5%, respectively, in RAW 264.7 cells (IC50s = 4.7 and 1.7 µM, respectively).1 28-Acetylbetulin induces cytotoxicity in a variety of cancer cells, including A549, HT-29, and MCF-7 cells (IC50s = 14.37, 10.96, and 11.38 µM, respectively).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Reyes, C.P., Núñez, M.J., Jiménez, I.A., et al. Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2. Bioorg. Med. Chem. 14(5), 1573-1579 (2006).

    2. Kommera, H., Kaluderović, G.N., Kalbitz, J., et al. Lupane triterpenoids--betulin and betulinic acid derivatives induce apoptosis in tumor cells. Invest. New Drugs 29(2), 266-272 (2011).