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Safety Information

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

B9757-5G:4548174008423
B9757-VAR:
B9757-1G:4548174008416
B9757-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT8364
MKCS6612
MKCQ0153
MKCN9623
MKCL8888

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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)
A bicentennial of betulin.
Hayek EWH, et al.
Phytochemistry, 28(9), 2229-2242 (1989)
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
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