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Chemical Structure| 472-15-1 Chemical Structure| 472-15-1

Structure of Betulinic acid
CAS No.: 472-15-1

Chemical Structure| 472-15-1

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Betulinic acid is a natural pentacyclic triterpene compound that inhibits eukaryotic topoisomerase I with an IC50 of 5 μM and exhibits anti-inflammatory, antimalarial, anti-HIV, and antitumor activities.

Synonyms: Lupatic acid; Betulic acid; Mairin

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Product Details of Betulinic acid

CAS No. :472-15-1
Formula : C30H48O3
M.W : 456.70
SMILES Code : C[C@@]1([C@@]2(CC[C@]3(C(C)([C@H](CC[C@@]3([C@]2(CC[C@@]1([C@]4([C@@H](CC5)C(C)=C)[H])[H])[H])C)O)C)[H])C)CC[C@]45C(O)=O
Synonyms :
Lupatic acid; Betulic acid; Mairin
MDL No. :MFCD00009619
InChI Key :QGJZLNKBHJESQX-FZFNOLFKSA-N
Pubchem ID :64971

Safety of Betulinic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of Betulinic acid

pyroptosis

Isoform Comparison

Biological Activity

Target
  • Topo I

    Eukaryotic topoisomerase I, IC50:5 μM

In Vitro:

Cell Line
Concentration Treated Time Description References
HT22 cells 12 µg/mL BA showed no significant toxicity to HT22 cells J Nanobiotechnology. 2022 Jan 21;20(1):39.
PANC-1 cells 5, 10, 20 μM 12, 24, 48 hours To assess the direct cytotoxicity of BA, which showed concentration- and time-dependent inhibition of cell proliferation. Cancer Res. 2011 Aug 1;71(15):5182-93.
FG cells 2.5, 5, 10 μM 48 hours To evaluate the cytotoxic effects of BA and MIT alone or in combination, showing inhibition of cell proliferation. Cancer Res. 2011 Aug 1;71(15):5182-93.
BxPC-3 cells 5, 10, 20 μM 12, 24, 48 hours To assess the direct cytotoxicity of BA, which showed concentration- and time-dependent inhibition of cell proliferation. Cancer Res. 2011 Aug 1;71(15):5182-93.
A172 cells 0, 3, 6, 12, 24, 48 µg/mL 24 hours BA NPs significantly inhibited A172 cell proliferation with IC50 of 8.5 µg/mL J Nanobiotechnology. 2022 Jan 21;20(1):39.
U87 cells 0, 3, 6, 12, 24, 48 µg/mL 24 hours BA NPs significantly inhibited U87 cell proliferation with IC50 of 12.1 µg/mL J Nanobiotechnology. 2022 Jan 21;20(1):39.
PANC-1 cells 50 μM 48 hours Gene expression profiles were analyzed by cDNA microarray after BA treatment, revealing significant downregulation of lamin B1. Clin Cancer Res. 2013 Sep 1;19(17):4651-61.

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT00346502 Dysplastic Nevus Syndrome Phase 1 Phase 2 Suspended(The study has been t... More >>emporarily suspended due to funding issues) Less << December 2015 United States, Illinois ... More >> University of Illinois at Chicago Medical Center Chicago, Illinois, United States, 60612 Less <<
NCT00701987 Melanoma PHASE1 UNKNOWN - Robert H. Lurie Comprehensive ... More >>Cancer Center, Northwestern University, Chicago, Illinois, 60611, United States Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.19mL

0.44mL

0.22mL

10.95mL

2.19mL

1.09mL

21.90mL

4.38mL

2.19mL

References

[1]Melzig MF, Bormann H. Betulinic acid inhibits aminopeptidase N activity. Planta Med. 1998 Oct;64(7):655-7.

[2]Fujioka T, Kashiwada Y, et al. 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. J Nat Prod. 1994 Feb;57(2):243-7.

[3]Chowdhury AR, Mandal S, Mittra B, Sharma S, Mukhopadhyay S, Majumder HK. Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives. Med Sci Monit. 2002 Jul;8(7):BR254-65. PMID: 12118187.

[4]Kasperczyk H, La Ferla-Brühl K, Westhoff MA, Behrend L, Zwacka RM, Debatin KM, Fulda S. Betulinic acid as new activator of NF-kappaB: molecular mechanisms and implications for cancer therapy. Oncogene. 2005 Oct 20;24(46):6945-56. doi: 10.1038/sj.onc.1208842. PMID: 16007147.

[5]Gao Y, Ma Q, Ma YB, Ding L, Xu XL, Wei DF, Wei L, Zhang JW. Betulinic acid induces apoptosis and ultrastructural changes in MDA-MB-231 breast cancer cells. Ultrastruct Pathol. 2018 Jan-Feb;42(1):49-54. doi: 10.1080/01913123.2017.1383548. Epub 2017 Dec 1. PMID: 29192840.

[6]Hashimoto F, Kashiwada Y, Cosentino LM, Chen CH, Garrett PE, Lee KH. Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem. 1997 Dec;5(12):2133-43. doi: 10.1016/s0968-0896(97)00158-2. PMID: 9459011.

[7]Kalra J, Lingaraju MC, Mathesh K, Kumar D, Parida S, Singh TU, Sharma AK, Kumar D, Tandan SK. Betulinic acid alleviates dextran sulfate sodium-induced colitis and visceral pain in mice. Naunyn Schmiedebergs Arch Pharmacol. 2018 Mar;391(3):285-297. doi: 10.1007/s00210-017-1455-3. Epub 2017 Dec 26. PMID: 29279966.

 

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