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Baccatin III information


Baccatin III
Names
IUPAC name
(2β,5α,7α,10α,13β)-4,10-Diacetoxy-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
Identifiers
CAS Number
  • 27548-93-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:32898
ChEMBL
  • ChEMBL288043
ChemSpider
  • 23486966
ECHA InfoCard 100.164.451 Edit this at Wikidata
PubChem CID
  • 65366
UNII
  • 40K5PZ0K67 checkY
CompTox Dashboard (EPA)
  • DTXSID301029474 Edit this at Wikidata
SMILES
  • CC1=C2[C@@H](C(=O)[C@@]3([C@@H](C[C@H]4[C@]([C@H]3[C@H]([C@@](C2(C)C)(C[C@H]1O)O)OC(=O)c5ccccc5)(CO4)OC(=O)C)O)C)OC(=O)C
Properties
Chemical formula
C31H38O11
Molar mass 586.62677 Da
Melting point 229 to 234 °C (444 to 453 °F; 502 to 507 K)
Acidity (pKa) 12.76
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Baccatin III is an isolate from the yew tree (Genera Taxus). Baccatin III is a precursor to the anti-cancer drug paclitaxel (Taxol).

In 2014, researchers reported introduction and expression of the endophytic fungal gene responsible for synthesizing baccatin III (10-deacetylbaccatin III 10-O-acetyltransferase), to the mushroom Flammulina velutipes.[1] Researchers achieved the same accomplishment with Escherichia coli in 2000.[2]

  1. ^ Han F, Kang LZ, Zeng XL, Ye ZW, Guo LQ, Lin JF (2014). "Bioproduction of baccatin III, an advanced precursor of paclitaxol with transgenic Flammulina velutipes expressing 10-Deacetylbaccatin III-10-O-acetyl transferase gene". J Sci Food Agric. 94 (12): 2376–2383. doi:10.1002/jsfa.6562. PMID 24403190.
  2. ^ Walker K, Croteau R (2000). "Molecular cloning of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli". Proc Natl Acad Sci U S A. 97 (2): 583–7. Bibcode:2000PNAS...97..583W. doi:10.1073/pnas.97.2.583. PMC 15373. PMID 10639122.

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Baccatin III

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Baccatin III is an isolate from the yew tree (Genera Taxus). Baccatin III is a precursor to the anti-cancer drug paclitaxel (Taxol). In 2014, researchers...

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Paclitaxel

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name Taxotere. Taxanes, including paclitaxel, 10-deacetylbaccatin III, baccatin III, paclitaxel C, and 7-epipaclitaxel, have been found in the leaves...

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Taxadiene

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hydroxylation reactions, and a few others, are needed to convert taxadiene to baccatin III. Enzymatically, taxadiene is produced from geranylgeranyl pyrophosphate...

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Takahashi Taxol total synthesis

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(the final product is baccatin III which lacks the amide tail found in taxol itself) and that it is racemic (the product baccatin III is optically inactive)...

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Organic synthesis

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Richard C. A.; Bornmann, William G. (1996-01-01). "Total Synthesis of Baccatin III and Taxol". Journal of the American Chemical Society. 118 (12): 2843–2859...

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Paclitaxel total synthesis

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potential. The paclitaxel molecule consists of a tetracyclic core called baccatin III and an amide tail. The core rings are conveniently called (from left...

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Docetaxel

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the formulation of docetaxel – an esterified product of 10-deacetyl baccatin III, which is extracted from the renewable and more readily available leaves...

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Vinyl iodide functional group

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Coburn, Craig A.; Di Grandi, Martin J. (1996-01-01). "Total Synthesis of Baccatin III and Taxol". Journal of the American Chemical Society. 118 (12): 2843–2859...

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Taxane

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Baccatin III (left) Paclitaxel (right)...

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Nocardioides luteus

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luteus can be used for enzymatic hydrolysis for producing 10-Deacetyl Baccatin III. Prauser, H. (24 January 2007). "Nocardioides luteus spec. nov". Zeitschrift...

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Nicolaou Taxol total synthesis

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triethylsilyl ether of the naturally occurring compound baccatin III. The related compound, 10-deacetylbaccatin III, is found in Taxus baccata, also known as the...

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Taxus globosa

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cell lines: Initiation, selection and characterization in terms of growth, and of baccatin III and paclitaxel production. Biocell, 34 (1), 1-6. v t e...

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Elias James Corey

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doi:10.1021/ja01084a034. Danishefsky; et al. (1996). "Total Synthesis of Baccatin III and Taxol". Journal of the American Chemical Society. 118 (12): 2843–2859...

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Mukaiyama Taxol total synthesis

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hydroxy carbonate 50, both TES groups were removed (HF, pyr) to triol 51 (baccatin III) and the C7 hydroxyl group was back-protected to 52. The amide tail synthesis...

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Danishefsky Taxol total synthesis

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resulted from the tail addition of the Ojima lactam to alcohol 51, which is baccatin III (the original target molecule of the Danishefsky synthesis). Alcohol...

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