| Identification | Back Directory | [Name]
1361-50-8
| [CAS]
1361-51-9 | [Synonyms]
Taxine B
1361-50-8
Valine Impurity 64
Benzenepropanoic acid, β-(dimethylamino)-, (3S,4aR,5S,6R,11R,12R,12aR)-11-(acetyloxy)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-5,6,12-trihydroxy-9,12a,13,13-tetramethyl-4-methylene-8-oxo-6,10-methanobenzocyclodecen-3-yl ester, (βS)- | [Molecular Formula]
C33H45NO8 | [MOL File]
1361-51-9.mol | [Molecular Weight]
583.712 |
| Chemical Properties | Back Directory | [Melting point ]
l13-5°C (approx.) | [Boiling point ]
676.9±55.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [solubility ]
Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
12.63±0.70(Predicted) | [color ]
White to Off-White | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Description]
A constituent of Taxus baccata, this alkaloid is amorphous and has [α]20D + 119°
(CHC13). The hydrochloride is also amorphous with no definite melting point.
The nitrate, however, can be crystallized from Et20-isopropanol, m.p. 190°C.
The base yields a diacetyl derivative which, although amorphous when obtained
from aqueous solution, m.p. 92°C, forms colourless crystals from EtOH, m.p.
161.5°C. This latter base has [α]20Do + 106.7° (c 2.0, CHC1 3) and gives a crystalline
hydrochloride from EtOH containing solvent of crystallization, m.p. 168-l70°C;
nitrate as colourless needles or plates from EtOH, m.p. 141.5°C and the
methiodide, m.p. 197°C. The structure of the alkaloid is that of Taxine I (q.v.)
minus two acetyl groups. | [Uses]
Taxine B is a toxic pyrrolizidine alkaloid obtained from rhodadendron and ragwort plants decomposition. An impurity in the biosynthesis of Paclitaxel (P132500) | [References]
Harrison, Scrowston, Lythgoe., 1. Chern. Soc., C, 1933 (1966) |
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