Global InformationTaxine alkaloids information
 Taxine A
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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
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| 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
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CAS Number
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3D model (JSmol)
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PubChem CID
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InChI
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SMILES
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| Properties | |
Chemical formula
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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).
Infobox references
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 Taxine B
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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
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CAS Number
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3D model (JSmol)
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InChI
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SMILES
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| Properties | |
Chemical formula
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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).
Infobox references
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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]
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]
- ^ Graf, Engelbert; Kirfel, Armin; Wolff, Gerd-Joachim; Breitmaier, Eberhard (1982-02-10). "Die Aufklärung von Taxin A ausTaxus baccata L.". Liebigs Annalen der Chemie. 1982 (2): 376–381. doi:10.1002/jlac.198219820222. ISSN 0170-2041.
- ^ Veterinary toxicology : basic and clinical principles. Gupta, Ramesh C. (Ramesh Chandra), 1949- (2nd ed.). Oxford: Academic. 2012. ISBN 9780123859266. OCLC 778786624.
{{cite book}}: CS1 maint: others (link) - ^ Miller, Roger W. (July 1980). "A Brief Survey of Taxus Alkaloids and Other Taxane Derivatives". Journal of Natural Products. 43 (4): 425–437. doi:10.1021/np50010a001. ISSN 0163-3864.
- ^ a b Cite error: The named reference
:0was invoked but never defined (see the help page). - ^ Constable, Peter D (2016-10-25). Veterinary medicine : a textbook of the diseases of cattle, horses, sheep, pigs and goats. Hinchcliff, Kenneth W. (Kenneth William), 1956-, Done, Stanley H.,, Grünberg, Walter,, Preceded by: Radostits, O. M. (11th ed.). St. Louis, Mo. ISBN 9780702070587. OCLC 962414947.
{{cite book}}: CS1 maint: location missing publisher (link) - ^ Alloatti, G.; Penna, C.; Levi, R. C.; Gallo, M. P.; Appendino, G.; Fenoglio, I. (1996). "Effects of yew alkaloids and related compounds on guinea-pig isolated perfused heart and papillary muscle". Life Sciences. 58 (10): 845–854. doi:10.1016/0024-3205(96)00018-5. ISSN 0024-3205. PMID 8602118.
- ^ Muriel, Le Roux (2016-11-26). Navelbine® and Taxotère® : histories of sciences. Gueritte, Françoise. London. ISBN 9780081011379. OCLC 964620092.
{{cite book}}: CS1 maint: location missing publisher (link)