WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 600110
CAS#: 32981-86-5
Description: 10-Deacetylbaccatin III, also known as 10-DAB or 10-DAB III, is a closely related natural organic compounds isolated from dried needles and small branches of the European yew tree (Taxus baccata).10-Deacetylbaccatin III is a precursor to the anti-cancer drug docetaxel (Taxotere). pacitaxel (taxol); cabazitaxel. 10-10-deacetylbaccatin III was found to selectively inhibit the growth of L. DONOVANI intracellular amastigotes within J774 murine macrophages in vitro at nanomolar concentrations with an IC(50) value of 70 nM.
MedKoo Cat#: 600110
Name: 10-Deacetylbaccatin III
CAS#: 32981-86-5
Chemical Formula: C29H36O10
Exact Mass: 544.23085
Molecular Weight: 544.59014
Elemental Analysis: C, 63.96; H, 6.66; O, 29.38
Synonym: 10DAB; 10DAB III; 10Deacetylbaccatin III. 10deacetyl baccatin III
IUPAC/Chemical Name: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate
InChi Key: YWLXLRUDGLRYDR-ZHPRIASZSA-N
InChi Code: InChI=1S/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1
SMILES Code: O=C(O[C@@H]([C@@]1([H])[C@@]2(C)[C@@H](O)C[C@@]3([H])OC[C@]31OC(C)=O)[C@]4(O)C[C@H](O)C(C)=C(C4(C)C)[C@@H](O)C2=O)C5=CC=CC=C5
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 544.59014 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: Grobosch T, Schwarze B, Stoecklein D, Binscheck T. Fatal poisoning with Taxus baccata: quantification of paclitaxel (taxol A), 10-deacetyltaxol, baccatin III, 10-deacetylbaccatin III, cephalomannine (taxol B), and 3,5-dimethoxyphenol in body fluids by liquid chromatography-tandem mass spectrometry. J Anal Toxicol. 2012 Jan-Feb;36(1):36-43. doi: 10.1093/jat/bkr012. PubMed PMID: 22290751.
2: Zhang JF, Gong S, Guo ZG. Effects of different elicitors on 10-deacetylbaccatin III-10-O-acetyltransferase activity and cytochrome P450 monooxygenase content in suspension cultures of Taxus cuspidata cells. Cell Biol Int Rep (2010). 2010;18(1):e00009. doi: 10.1042/CBR20110001. Epub 2011 Apr 8. PubMed PMID: 23119144; PubMed Central PMCID: PMC3475439.
3: Fu Y, Zu Y, Li S, Sun R, Efferth T, Liu W, Jiang S, Luo H, Wang Y. Separation of 7-xylosyl-10-deacetyl paclitaxel and 10-deacetylbaccatin III from the remainder extracts free of paclitaxel using macroporous resins. J Chromatogr A. 2008 Jan 4;1177(1):77-86. Epub 2007 Nov 17. PubMed PMID: 18054030.
4: Georgopoulou K, Smirlis D, Bisti S, Xingi E, Skaltsounis L, Soteriadou K. In vitro activity of 10-deacetylbaccatin III against Leishmania donovani promastigotes and intracellular amastigotes. Planta Med. 2007 Aug;73(10):1081-8. Epub 2007 Aug 9. PubMed PMID: 17691059.
5: Guo B, Kai G, Gong Y, Jin H, Wang Y, Miao Z, Sun X, Tang K. Molecular cloning and heterologous expression of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus x media. Mol Biol Rep. 2007 Jun;34(2):89-95. Epub 2006 Nov 9. PubMed PMID: 17094009.
6: Frapolli R, Marangon E, Zaffaroni M, Colombo T, Falcioni C, Bagnati R, Simone M, D'Incalci M, Manzotti C, Fontana G, Morazzoni P, Zucchetti M. Pharmacokinetics and metabolism in mice of IDN 5390 (13-(N-Boc-3-i-butylisoserinoyl)-C-7,8-seco-10-deacetylbaccatin III), a new oral c-seco-taxane derivative with antiangiogenic property effective on paclitaxel-resistant tumors. Drug Metab Dispos. 2006 Dec;34(12):2028-35. Epub 2006 Sep 8. PubMed PMID: 16963486.
7: Barboni L, Giarlo G, Ballini R, Fontana G. 14Beta-hydroxy-10-deacetylbaccatin III as a convenient, alternative substrate for the improved synthesis of methoxylated second-generation taxanes. Bioorg Med Chem Lett. 2006 Oct 15;16(20):5389-91. Epub 2006 Aug 4. PubMed PMID: 16890428.
8: Hanson RL, Parker WL, Patel RN. Enzymatic C-4 deacetylation of 10-deacetylbaccatin III. Biotechnol Appl Biochem. 2006 Sep;45(Pt 2):81-5. PubMed PMID: 16722823.
9: Yang T, Li M, Chen JM. Conversion of taxane glycosides to 10-deacetylbaccatin III. Nat Prod Res. 2006 Feb;20(2):119-24. PubMed PMID: 16319004.
10: Fang J, Ewald D. Expression cloned cDNA for 10-deacetylbaccatin III-10-O-acetyltransferase in Escherichia coli: a comparative study of three fusion systems. Protein Expr Purif. 2004 May;35(1):17-24. PubMed PMID: 15039061.
