WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200160
CAS#: 472-15-1
Description: Betulinic acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal.and brain tumor cells.
MedKoo Cat#: 200160
Name: Betulinic acid
CAS#: 472-15-1
Chemical Formula: C30H48O3
Exact Mass: 456.36035
Molecular Weight: 456.7
Elemental Analysis: C, 78.90; H, 10.59; O, 10.51
Synonym: ALS357; ALS 357; ALS-357; Mairin; Betulinic acid;
IUPAC/Chemical Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
InChi Key: QGJZLNKBHJESQX-FZFNOLFKSA-N
InChi Code: 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
SMILES Code: O=C([C@]1(CC[C@H]2C(C)=C)[C@@]2([H])[C@@]3([H])CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]4(C)[C@]3(C)CC1)O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 456.7 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Chaouki W, Leger DY, Eljastimi J, Beneytout JL, Hmamouchi M. Antiproliferative effect of extracts from Aristolochia baetica and Origanum compactum on human breast cancer cell line MCF-7. Pharm Biol. 2010 Mar;48(3):269-74. PubMed PMID: 20645812.
2: Parrondo R, Pozas Ade L, Reiner T, Rai P, Perez-Stable C. NF-kappaB activation enhances cell death by antimitotic drugs in human prostate cancer cells. Mol Cancer. 2010 Jul 9;9:182. PubMed PMID: 20618955.
3: Li Y, He K, Huang Y, Zheng D, Gao C, Cui L, Jin YH. Betulin induces mitochondrial cytochrome c release associated apoptosis in human cancer cells. Mol Carcinog. 2010 Jul;49(7):630-40. PubMed PMID: 20564340.
4: Eichenmüller M, Hemmerlein B, von Schweinitz D, Kappler R. Betulinic acid induces apoptosis and inhibits hedgehog signalling in rhabdomyosarcoma. Br J Cancer. 2010 Jun 29;103(1):43-51. Epub 2010 Jun 1. PubMed PMID: 20517313; PubMed Central PMCID: PMC2905279.
5: Cheng MJ, Chen JJ, Wu MD, Yang PS, Yuan GF. Isolation and structure determination of one new metabolite isolated from the red fermented rice of Monascus purpureus. Nat Prod Res. 2010 Jun;24(10):979-88. PubMed PMID: 20496238.
6: Ahmad FB, Ghaffari Moghaddam M, Basri M, Abdul Rahman MB. Anticancer activity of 3-O-acylated betulinic acid derivatives obtained by enzymatic synthesis. Biosci Biotechnol Biochem. 2010;74(5):1025-9. Epub 2010 May 7. PubMed PMID: 20460723.
7: Kommera H, Kaluderović GN, Dittrich S, Kalbitz J, Dräger B, Mueller T, Paschke R. Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity. Bioorg Med Chem Lett. 2010 Jun 1;20(11):3409-12. Epub 2010 Apr 18. PubMed PMID: 20451375.
8: Chadalapaka G, Jutooru I, Burghardt R, Safe S. Drugs that target specificity proteins downregulate epidermal growth factor receptor in bladder cancer cells. Mol Cancer Res. 2010 May;8(5):739-50. Epub 2010 Apr 20. PubMed PMID: 20407012; PubMed Central PMCID: PMC2872686.
9: da Silveira CV, Trevisan MT, Rios JB, Erben G, Haubner R, Pfundstein B, Owen RW. Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart. Food Chem Toxicol. 2010 Jun;48(6):1597-606. Epub 2010 Mar 27. PubMed PMID: 20347919.
10: Eder-Czembirek C, Erovic BM, Czembirek C, Brunner M, Selzer E, Pötter R, Thurnher D. Betulinic Acid a Radiosensitizer in Head and Neck Squamous Cell Carcinoma Cell Lines. Strahlenther Onkol. 2010 Feb 22. [Epub ahead of print] PubMed PMID: 20339825.
Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), selfheal (Prunella vulgaris), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. see: http://en.wikipedia.org/wiki/Betulinic_acid .
