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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
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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,[1] is found in the bark of birch trees.[2] It undergoes rearrangement in the presence of acid agents to form allobetulin.[3]

Application

Betulin may be used in the preparation of betulinic acid,[4] which shows anti-HIV, antimalarial and anti-inflammatory activities.[2]

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
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)
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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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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