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91466

Betulinic acid

analytical standard

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
NACRES:
NA.24
PubChem Substance ID:
329770040
UNSPSC Code:
85151701
EC Number:
207-448-8
MDL number:
MFCD00009619
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grade

analytical standard

Quality Level

100

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

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.

Other Notes

This compound is commonly found in plants of the genus: glycyrrhiza melissa

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH1050
BCCD9332
BCCB6774
BCBZ2182
BCBW1969

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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)
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)
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)
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Global Trade Item Number

SKUGTIN
91466-10MG04061833263228