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855057

Sigma-Aldrich

Betulinsäure

technical grade, 90%

Synonym(e):

3β-Hydroxy-20(29)-lupaene-28-oic acid, Mairin

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About This Item

Empirische Formel (Hill-System):
C30H48O3
CAS-Nummer:
472-15-1
Molekulargewicht:
456.70
EG-Nummer:
207-448-8
MDL-Nummer:
MFCD00009619
UNSPSC-Code:
85151701
PubChem Substanz-ID:
24888370
NACRES:
NA.22

Qualität

technical grade

Qualitätsniveau

100

Assay

90%

Form

powder

Optische Aktivität

[α]20/D +7.8°, c = 0.9 in pyridine

mp (Schmelzpunkt)

295-298 °C (dec.) (lit.)

Lagertemp.

2-8°C

SMILES String

CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O

InChI

1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

InChIKey

QGJZLNKBHJESQX-FZFNOLFKSA-N

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Allgemeine Beschreibung

Betulinic acid is a lupane-type triterpene, which can be prepared from betulin via oxidation using chromium oxide (VI). Along with anti-HIV-1 and anti-tumor activity, it also shows other bioactivities such as anti-inflammatory, antibacterial, in vitro antimalarial, anthelmintic and antioxidant activities.

Biochem./physiol. Wirkung

Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
STBJ9909
STBJ1809
STBH3078
STBF5901V
STBD6023V

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Ursolsäure ≥90%

Sigma-Aldrich

U6753

Ursolsäure

Maslinsäure ≥98% (HPLC)

Sigma-Aldrich

M6699

Maslinsäure

Lupeol ≥94%

Sigma-Aldrich

L5632

Lupeol

Oregonin ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00088

Oregonin

Lupeol analytical standard

Supelco

18692

Lupeol

2’-C-Methylcytidine ≥95% (HPLC), powder

Sigma-Aldrich

M4949

2′-C-Methylcytidine

β-Sitosterin-β-D-glucosid analytical standard

Supelco

89851

β-Sitosterin-β-D-glucosid

Li Kong et al.
Antioxidants (Basel, Switzerland), 10(2) (2021-01-28)
T-2 toxin, which is mainly produced by specific strains of Fusarium in nature, can induce immunotoxicity and oxidative stress, resulting in immune organ dysfunction and apoptosis. Betulinic acid (BA), a pentacyclic triterpenoids from nature plants, has been demonstrated to possess
Sami Alakurtti et al.
Bioorganic & medicinal chemistry, 18(4), 1573-1582 (2010-02-02)
Betulin, a naturally occurring abundant triterpene is converted in four steps to 3,28-di-O-acetyllupa-12,18-diene. When various 4-substituted urazoles were oxidized to the corresponding urazines with iodobenzene diacetate in the presence of 3,28-di-O-acetyllupa-12,18-diene, new heterocyclic betulin derivatives were produced. These betulin derivatives
Rita C Santos et al.
Bioorganic & medicinal chemistry, 17(17), 6241-6250 (2009-08-14)
A series of new imidazole carboxylic esters (carbamates) and N-acylimidazole derivatives of betulin and betulinic acid (14-29) have been synthesized. The new compounds were screened for in vitro cytotoxicity activity against human cancer cell lines HepG2, Jurkat and HeLa. A
Yan-Fang Sun et al.
Food chemistry, 138(2-3), 1998-2007 (2013-02-16)
Betulinic acid (BA), a natural pentacyclic triterpenoid, was isolated from sour jujube fruits for the first time. An inclusion complex comprising BA and β-cyclodextrin (β-CD) was formed to improve the dissolution of BA, but little is known about its anticancer
Perumal Yogeeswari et al.
Current medicinal chemistry, 12(6), 657-666 (2005-03-26)
Betulinic acid is a naturally occurring pentacyclic triterpenoid and has been shown to exhibit a variety of biological activities including inhibition of human immunodeficiency virus (HIV), antibacterial, antimalarial, antiinflammatory, anthelmintic and antioxidant properties. This article reports a survey of the
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