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B8154

Sigma-Aldrich

Baccatin III

≥95% (HPLC)

Synonym(s):

O-De[(2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropanoyl]paclitaxel

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About This Item

Empirical Formula (Hill Notation):
C31H38O11
CAS Number:
27548-93-2
Molecular Weight:
586.63
MDL number:
MFCD00153921
UNSPSC Code:
12352005
PubChem Substance ID:
57653960
NACRES:
NA.22

Quality Level

100

Assay

≥95% (HPLC)

form

powder

storage temp.

2-8°C

SMILES string

CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@H]3OC[C@@]3(OC(C)=O)[C@H]2[C@H](OC(=O)c4ccccc4)[C@]5(O)C[C@H](O)C(C)=C1C5(C)C

InChI

1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,26-,29+,30-,31+/m0/s1

InChI key

OVMSOCFBDVBLFW-VHLOTGQHSA-N

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Related Categories

Application

Precursor to paclitaxel

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H335,H340,H350

Hazard Classifications

Carc. 1B - Eye Irrit. 2 - Muta. 1B - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Bing-Juan Li et al.
Nature communications, 8, 15544-15544 (2017-05-19)
The natural concentration of the anticancer drug Taxol is about 0.02% in yew trees, whereas that of its analogue 7-β-xylosyl-10-deacetyltaxol is up to 0.5%. While this compound is not an intermediate in Taxol biosynthetic route, it can be converted into
Chia-Hsiang Hwang et al.
Phytotherapy research : PTR, 26(4), 528-534 (2011-09-15)
7,7''-Dimethoxyagastisflavone (DMGF), a biflavonoid isolated from the needles of Taxus × media cv. Hicksii, was evaluated for its antiproliferative and antineoplastic effects in three human cancer cell lines. Interestingly, DMGF caused cell death via different pathways in different cancer cells.
Jared T Spletstoser et al.
Bioorganic & medicinal chemistry letters, 16(3), 495-498 (2005-11-18)
A single-site modification of paclitaxel analogs at the C10 position on the baccatin III core that reduces interaction with P-glycoprotein in bovine brain microvessel endothelial cells is described. Modification and derivatization of the C10 position were carried out using a
Elizabeth M Heider et al.
Physical chemistry chemical physics : PCCP, 9(46), 6083-6097 (2008-01-03)
The three-dimensional structure of a unique polymorph of the anticancer drug paclitaxel (Taxol) is established using solid state NMR (SSNMR) tensor ((13)C & (15)N) and heteronuclear correlation ((1)H-(13)C) data. The polymorph has two molecules per asymmetric unit (Z' = 2)
Hiroshi Izumi et al.
The Journal of organic chemistry, 73(6), 2367-2372 (2008-02-16)
The comparison between measured and conformer-weighted calculated VCD spectra of the baccatin III ring of paclitaxel and visualization of the conformations using the new code for structure-activity relationships are reported for the first time. The VCD spectrum of paclitaxel closely
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