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Merck

91466

Supelco

Betulinic acid

analytical standard

Synonim(y):

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

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About This Item

Wzór empiryczny (zapis Hilla):
C30H48O3
Numer CAS:
Masa cząsteczkowa:
456.70
Numer WE:
Numer MDL:
Kod UNSPSC:
85151701
Identyfikator substancji w PubChem:
NACRES:
NA.24

klasa czystości

analytical standard

Poziom jakości

Próba

≥97.0% (HPLC)

okres trwałości

limited shelf life, expiry date on the label

metody

HPLC: suitable
gas chromatography (GC): suitable

mp

295-298 °C (dec.) (lit.)

Zastosowanie

food and beverages

format

neat

temp. przechowywania

2-8°C

ciąg SMILES

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

Klucz InChI

QGJZLNKBHJESQX-FZFNOLFKSA-N

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Opis ogólny

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.

Zastosowanie

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.

Działania biochem./fizjol.

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.

Opakowanie

Bottomless glass bottle. Contents are inside inserted fused cone.

Inne uwagi

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

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable


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Certyfikaty analizy (CoA)

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Slide 1 of 3

1 of 3

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)
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)
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
Teresita Reiner et al.
PloS one, 8(2), e56234-e56234 (2013-02-21)
Inhibition of the ubiquitin-proteasome system (UPS) of protein degradation is a valid anti-cancer strategy and has led to the approval of bortezomib for the treatment of multiple myeloma. However, the alternative approach of enhancing the degradation of oncoproteins that are

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