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855057

Sigma-Aldrich

Betulinic acid

technical grade, 90%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C30H48O3
Número de CAS:
472-15-1
Peso molecular:
456.70
EC Number:
207-448-8
MDL number:
MFCD00009619
UNSPSC Code:
85151701
PubChem Substance ID:
24888370
NACRES:
NA.22

grade

technical grade

assay

90%

form

powder

optical activity

[α]20/D +7.8°, c = 0.9 in pyridine

mp

295-298 °C (dec.) (lit.)

storage temp.

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

InChI key

QGJZLNKBHJESQX-FZFNOLFKSA-N

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General description

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 Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Maslinic acid ≥98% (HPLC)

Sigma-Aldrich

M6699

Maslinic acid

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-Sitosterol β-D-glucoside analytical standard

Supelco

89851

β-Sitosterol β-D-glucoside

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
Rafael Alcalá-Vida et al.
EMBO molecular medicine, 13(2), e12105-e12105 (2020-12-29)
Lamins are crucial proteins for nuclear functionality. Here, we provide new evidence showing that increased lamin B1 levels contribute to the pathophysiology of Huntington's disease (HD), a CAG repeat-associated neurodegenerative disorder. Through fluorescence-activated nuclear suspension imaging, we show that nucleus
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
David A Eiznhamer et al.
IDrugs : the investigational drugs journal, 7(4), 359-373 (2004-04-02)
Betulinic acid is a naturally occurring pentacyclic triterpenoid which has demonstrated selective cytotoxicity against a number of specific tumor types, a variety of infectious agents such as HIV, malaria and bacteria, and the inflammatory process in general. Biological activity was
Hedgehog-Gli signaling pathway inhibitors as anticancer agents.
Neeraj Mahindroo et al.
Journal of medicinal chemistry, 52(13), 3829-3845 (2009-03-25)
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