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91466

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Betulinic acid

analytical standard

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Synonym(s):
3β-Hydroxy-20(29)-lupaene-28-oic acid, Lupatic acid, Mairin
Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
Molecular Weight:
456.70
EC Number:
MDL number:
PubChem Substance ID:

grade

analytical standard

Quality Level

assay

≥97.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

295-298 °C (dec.) (lit.)

application(s)

food and beverages

format

neat

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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This Item
855057B8936PHL83839
Betulinic acid analytical standard

91466

Betulinic acid

Betulinic acid technical grade, 90%

855057

Betulinic acid

Betulinic acid ≥98% (HPLC)

B8936

Betulinic acid

Betulonic acid phyproof® Reference Substance

PHL83839

Betulonic acid

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

-

technique(s)

-

technique(s)

-

format

neat

format

-

format

-

format

neat

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

grade

analytical standard

grade

technical grade

grade

-

grade

primary reference standard

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

General description

Betulinic acid is a pentacyclic triterpene, isolated from the leaves of Syzigium claviflorum. It is found to be an inhibitor of HIV replication in H9 lymphocyte cells.

Application

Betulinic acid may be used as a reference standard in the determination of betulinic acid in white birch bark using reversed-phase high-performance liquid chromatography (RP-HPLC).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Simultaneous determination of betulin and betulinic acid in white birch bark using RP-HPLC.
Zhao G, et al.
Journal of Pharmaceutical and Biomedical Analysis, 43(3), 959-962 (2007)
Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids.
Fujioka T, et al.
Journal of Natural Products, 57(2), 243-247 (1994)
Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis.
Pisha E, et al.
Nature Medicine, 1(10), 1046-1046 (1995)
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
Christopher Aiken et al.
Trends in molecular medicine, 11(1), 31-36 (2005-01-15)
Betulinic acid (BA) derivatives are low molecular weight organic compounds synthesized from a plant-derived natural product. Several BA derivatives are potent and highly selective inhibitors of HIV-1. Depending on the specific side-chain modification, these compounds function by inhibiting HIV fusion

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