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Merck
CN

SML2070

23-Hydroxybetulinic acid

≥98% (HPLC)

Synonym(s):

(3β,4α)-3,23-Dihydroxylup-20(29)-en-28-oic acid, 3β,23-Dihydroxylup-20(29)-en-28-oic acid, 3aH-Cyclopenta[a]chrysene, lup-20(29)-en-28-oic acid deriv., Anemosapogenin

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About This Item

Empirical Formula (Hill Notation):
C30H48O4
CAS Number:
85999-40-2
Molecular Weight:
472.70
UNSPSC Code:
12352106
NACRES:
NA.77
MDL number:
MFCD28126999

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InChI

1S/C30H48O4/c1-18(2)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h19-24,31-32H,1,7-17H2,2-6H3,(H,33,34)/t19-,20+,21+,22+,23-,24+,26-,27-,28+,29+,30-/m0/s1

SMILES string

O[C@H]1CC[C@@]2(C)[C@](CC[C@]3(C)[C@]2([H])CC[C@@]4([H])[C@@]3(C)CC[C@]5(C(O)=O)[C@]4([H])[C@H](C(C)=C)CC5)([H])[C@]1(C)CO

InChI key

HXWLKAXCQLXHML-WGOZWDAUSA-N

assay

≥98% (HPLC)

form

powder

storage condition

under inert gas

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

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Biochem/physiol Actions

23-Hydroxybetulinic acid is a cytotoxic agent from rizoma of Pulsatilla chinensis (Bunge) Regel. Anticancer activity of 23-Hydroxybetulinic acid is associated with depolarizations of the mitochondrial membrane potential and subsequent cell apoptosis. Additionally it induces autophagic cell death in HL-60 cells via the up regulation of Beclin-1.
cytotoxic agent from Pulsatilla chinensis

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000026271
0000026270
0000020583

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Nan Yao et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 37(3), 838-852 (2015-09-19)
Hepatocellular carcinoma (HCC) is the most common type of liver cancer. At present, only sorafenib is approved to treat HCC. In this study, we found that a 23-hydroxybetulinic acid derivative, B4G2, exhibited potent antiproliferative activity in HCC cell lines. We
Yi Bi et al.
Molecules (Basel, Switzerland), 17(8), 8832-8841 (2012-07-27)
23-Hydroxybetulinic acid (1) served as the precursor for the synthesis of C-28 ester derivatives. The target compounds were evaluated in vitro for their antitumor activities against five cell lines (A549, BEL-7402, SF-763, B16 and HL-60). Among the obtained compounds, 6i
Ming Liu et al.
Pharmaceutical biology, 53(1), 1-9 (2014-07-16)
The rizoma of Pulsatilla chinensis (Bunge) Regel has been used as a traditional Chinese medicinal herb for thousands of years. Total saponins from P. chinensis can induce the apoptosis of solid cancer cells; however, their activity on chronic myeloid leukemia

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