Taxine alkaloids
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Taxine alkaloids, which are often named under the collective title of taxines, are the toxic chemicals that can be isolated from the yew tree.[2][3] The amount of taxine alkaloids depends on the species of yew, with Taxus baccata and Taxus cuspidata containing the most.[4] The major taxine alkaloids are taxine A and taxine B although there are at least 10 different alkaloids.[5] Until 1956, it was believed that all the taxine alkaloids were one single compound named taxine.[4]
Taxine A | |
Names | |
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IUPAC name
2α,13α-Diacetoxy-7β,10β-dihydroxy-9-oxo-2(3→20)-abeotaxa-4(20),11-dien-5α-yl (2R,3S)-3-(dimethylamino)-2-hydroxy-3-phenylpropanoate | |
Other names
(1R,2S,3E,5S,7S,8S,10R,13S)-2,13-Diacetoxy-7,10-dihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.14,8]hexadeca-3,11-dien-5-yl (2R,3S)-3-(dimethylamino)-2-hydroxy-3-phenylpropanoate | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChemSpider | |
KEGG | |
PubChem CID |
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UNII | |
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Properties | |
C35H47NO10 | |
Molar mass | 641.751 g·mol−1 |
Melting point | 204-206 °C[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Taxine B | |
Names | |
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IUPAC name
10β-Acetoxy-1,2α,9α-trihydroxy-13-oxotaxa-4(20),11-dien-5α-yl (3R)-3-(dimethylamino)-3-phenylpropanoate | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChemSpider | |
KEGG | |
PubChem CID |
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Properties | |
C33H45NO8 | |
Molar mass | 583.722 g·mol−1 |
Melting point | 115 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The taxine alkaloids are cardiotoxins with taxine B being the most active.[6] Taxine alkaloids have no medical uses but Paclitaxel and other taxanes that can be isolated from yews have been used as chemotherapy drugs.[7]