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855057

Sigma-Aldrich

Betulinic acid

technical grade, 90%

Synonyma:

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

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
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About This Item

Empirický vzorec (Hillův zápis):
C30H48O3
Číslo CAS:
472-15-1
Molekulová hmotnost:
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)

Osvědčení o analýze (COA)

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Sigma-Aldrich

U6753

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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
Hedgehog-Gli signaling pathway inhibitors as anticancer agents.
Neeraj Mahindroo et al.
Journal of medicinal chemistry, 52(13), 3829-3845 (2009-03-25)
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
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