10-Deacetylbaccatin-III

For research use only. Not for therapeutic Use.

  • CAT Number: A000200
  • CAS Number: 32981-86-5
  • Molecular Formula: C29H36O10
  • Molecular Weight: 544.6
  • Purity: ≥95%
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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.


Catalog Number A000200
CAS Number 32981-86-5
Synonyms

32981-86-5; UNII-4K6EWW2Z45; 10-Deacetylbaccatin; CHEBI:18193; 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate

Molecular Formula C29H36O10
Purity ≥95%
Target Disease Research Fields
Solubility >22.3mg/mL in DMSO
Storage -20°C
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
InChIKey YWLXLRUDGLRYDR-ZHPRIASZSA-N
SMILES CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)O
Reference

1: Li BJ, Wang H, Gong T, Chen JJ, Chen TJ, Yang JL, Zhu P. Improving
10-deacetylbaccatin III-10-β-O-acetyltransferase catalytic fitness for Taxol
production. Nat Commun. 2017 May 18;8:15544. doi: 10.1038/ncomms15544. PubMed
PMID: 28516951; PubMed Central PMCID: PMC5454391.
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2: Yanagi M, Ninomiya R, Ueda Y, Furuta T, Yamada T, Sunazuka T, Kawabata T.
Organocatalytic Site-Selective Acylation of 10-Deacetylbaccatin III. Chem Pharm
Bull (Tokyo). 2016 Jul 1;64(7):907-12. doi: 10.1248/cpb.c16-00037. Epub 2016 Feb
23. PubMed PMID: 26903156.
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3: Zhang X, Lv J, Wang L, Shao H. Comparison of Pharmacokinetics and
Biodistribution of 10-Deacetylbaccatin III after Oral Administration as Pure
Compound or in Taxus chinensis Extract: A Pilot Study. Planta Med. 2016
Feb;82(3):230-7. doi: 10.1055/s-0035-1558207. Epub 2016 Feb 2. PubMed PMID:
26838275.

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4: Han F, Kang LZ, Zeng XL, Ye ZW, Guo LQ, Lin JF. Bioproduction of baccatin III,
an advanced precursor of paclitaxol, with transgenic Flammulina velutipes
expressing the 10-deacetylbaccatin III-10-O-acetyl transferase gene. J Sci Food
Agric. 2014 Sep;94(12):2376-83. doi: 10.1002/jsfa.6562. Epub 2014 Feb 13. PubMed
PMID: 24403190.
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5: 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.
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6: 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.
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7: 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.
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8: 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.
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9: 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.

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10: 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.

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