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B9757

Sigma-Aldrich

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
EC Number:
207-475-5
MDL number:
MFCD00016802
UNSPSC Code:
12352002
PubChem Substance ID:
57653970
NACRES:
NA.22

Quality Level

100

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
GHS08

Signal Word

Warning

Hazard Statements

H371

Hazard Classifications

STOT SE 2

Target Organs

Eyes,Central nervous system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ0153
MKCN9623
MKCL8888
MKCK2258
MKCG3208

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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)
A bicentennial of betulin.
Hayek EWH, et al.
Phytochemistry, 28(9), 2229-2242 (1989)
Sami Alakurtti et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 29(1), 1-13 (2006-05-24)
Betulin (lup-20(29)-ene-3beta,28-diol) is an abundant naturally occurring triterpene and it is found predominantly in bushes and trees forming the principal extractive (up to 30% of dry weight) of the bark of birch trees. Presently, there is no significant use for
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