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855057

Sigma-Aldrich

Betulinic acid

technical grade, 90%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
472-15-1
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Simone Fulda et al.
Drug discovery today, 14(17-18), 885-890 (2009-06-13)
Betulinic acid (BA) is a naturally occurring pentacyclic triterpene that exhibits a variety of biological activities including potent antitumor properties. This anticancer activity has been linked to its ability to directly trigger mitochondrial membrane permeabilization, a central event in the
Franziska B Mullauer et al.
Anti-cancer drugs, 21(3), 215-227 (2010-01-16)
New therapies using novel mechanisms to induce tumor cell death are needed with plants playing a crucial role as a source for potential anticancer compounds. One highly promising class of natural compounds are the triterpenoids with betulinic acid (BetA) as
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