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Merck
CN

B9757

Betulin

≥98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C30H50O2
CAS Number:
473-98-3
Molecular Weight:
442.72
NACRES:
NA.22
PubChem Substance ID:
57653970
UNSPSC Code:
12352002
EC Number:
207-475-5
MDL number:
MFCD00016802

Key Documents

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Product Name

Betulin, ≥98%

InChI key

FVWJYYTZTCVBKE-ROUWMTJPSA-N

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

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]

assay

≥98%

form

powder

mp

256-257 °C (lit.)

storage temp.

2-8°C

Quality Level

100

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Application

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

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.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H371

Hazard Classifications

STOT SE 2

target_organs

Eyes,Central nervous system

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX9521
MKCX5778
MKCT8364
MKCS6612
MKCQ0153

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Betulin and its derivatives. Chemistry and biological activity.
Tolstikov GA, et al.
Chemistry for Sustainable Development, 13, 1-29 (2005)
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
A concise semi-synthetic approach to betulinic acid from betulin.
Kim DSHL, et al.
Synthetic Communications, 27(9), 1607-1612 (1997)
Cristina A Dehelean et al.
Journal of biomedical nanotechnology, 9(4), 577-589 (2013-04-30)
Betulin (Bet), the main component of birch tree bark, has been recently reported to exert anticancer activity in several cell lines; however the underlying mechanisms are only partially elucidated. The aims of the present work were to assess the in
A bicentennial of betulin.
Hayek EWH, et al.
Phytochemistry, 28(9), 2229-2242 (1989)
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