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Merck

B9757

Sigma-Aldrich

Betulin

≥98%

Sinónimos:

Betulinic alcohol, Betulinol, Betulol, Lup-20(29)-ene-3β,28-diol, Trochol

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About This Item

Fórmula empírica (notación de Hill):
C30H50O2
Número de CAS:
Peso molecular:
442.72
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥98%

form

powder

mp

256-257 °C (lit.)

storage temp.

2-8°C

SMILES string

[H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@]5(CO)CC[C@@H](C(C)=C)[C@]25[H]

InChI

1S/C30H50O2/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/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1

InChI key

FVWJYYTZTCVBKE-ROUWMTJPSA-N

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General description

Betulin, a triterpene with lupane nucleus, is found in the bark of birch trees. It undergoes rearrangement in the presence of acid agents to form allobetulin.

Application

Betulin may be used in the preparation of betulinic acid, which shows anti-HIV, antimalarial and anti-inflammatory activities.

Pictograms

Health hazard

signalword

Warning

hcodes

Hazard Classifications

STOT SE 2

target_organs

Eyes,Central nervous system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3


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Cindy Horwedel et al.
Journal of medicinal chemistry, 53(13), 4842-4848 (2010-06-10)
A novel approach to circumvent multidrug resistance is hybridization of natural products in dimers. We analyzed homodimers of two artesunic acid molecules and heterohybrids of artesunic acid and betulin in human CCRF-CEM and multidrug-resistant P-glycoprotein-overexpressing CEM/ADR5000 leukemia cells. Multidrug-resistant cells
Betulin and its derivatives. Chemistry and biological activity.
Tolstikov GA, et al.
Chemistry for Sustainable Development, 13, 1-29 (2005)
A concise semi-synthetic approach to betulinic acid from betulin.
Kim DSHL, et al.
Synthetic Communications, 27(9), 1607-1612 (1997)
Milan Urban et al.
Bioorganic & medicinal chemistry, 20(11), 3666-3674 (2012-05-04)
The aim of this work was to synthesize a set of heterocyclic derivatives of lupane, lup-20(29)-ene, and 18α-oleanane, and to investigate their cytotoxic activities. Some of those heterocycles were previously known in the oleanane (allobetulin) group; however, to our knowledge
Sayan Chowdhury et al.
Molecular pharmacology, 80(4), 694-703 (2011-07-14)
Toward developing antileishmanial agents with mode of action targeted to DNA topoisomerases of Leishmania donovani, we have synthesized a large number of derivatives of betulin. The compound, a natural triterpene isolated from the cork layer of Betula spp. plants exhibits

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