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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

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

Certificates of Analysis (COA)

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Haibo Ge et al.
The Journal of organic chemistry, 72(3), 756-759 (2007-01-27)
The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in
Catherine Loncaric et al.
Chemistry & biology, 13(3), 309-317 (2006-04-28)
The 10beta-acetyltransferase on the biosynthetic pathway of the antineoplastic drug Taxol catalyzes the regiospecific transfer of the acetyl group of acetyl-coenzyme A (CoA) to 10-deacetylbaccatin III. We demonstrate that in addition to acetyl group transfer, the overexpressed enzyme also catalyzes
Xin Che et al.
Journal of pharmaceutical and biomedical analysis, 55(5), 1190-1196 (2011-05-03)
The isolation and characterization of the process related impurities and degradation products of larotaxel drug substance were described. Forced degradation of larotaxel was carried out under acidic, basic, oxidation, light and thermal conditions to assess the nature of the impurities.
Young-Hee Lee et al.
International immunopharmacology, 21(2), 487-493 (2014-06-25)
Myeloid-derived suppressor cells (MDSCs) mediate tumor-associated immune suppression in both cancer patients and tumor-bearing animals. Reduction or elimination of MDSCs reduces the rate of tumor progression and improves cancer therapies that employ mechanisms of immunity. Here we show that baccatin
Mohammad K Parvez et al.
Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society, 27(3), 389-400 (2019-04-13)
Despite high anti-HBV efficacies, while the nucleoside analogs (e.g., lamivudine) lead to the emergence of drug-resistance, interferons (e.g., IFN-α causes adverse side-effects. Comparatively, various natural or plant products have shown similar or even better efficacy. Hence, new antiviral strategies must
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