10-deacetylbaccatin III

Structural formula
General
Surname	10-deacetylbaccatin III
Molecular formula	C 29 H 36 O 10
Brief description	colorless solid
External identifiers / databases
CAS number 32981-86-5 EC number 608-810-1 ECHA InfoCard 100.128.614 PubChem 154272 Wikidata Q163856
properties
Molar mass	544.59 g mol −1
Physical state	firmly
Melting point	231-236 ° C
solubility	almost insoluble in water soluble in methanol soluble in supercritical carbon dioxide
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

10-Deacetylbaccatin III is a representative of the deacetylbaccatin, a group of closely related natural substances that are obtained from yew trees (Taxus). It is a raw material for the manufacture of anti-cancer drugs.

History and occurrence

Parts of the European yew tree

Like the anti-inflammatory agent taxol, 10-deacetylbaccatin is a naturally occurring taxane . Taxol (Paclitaxel) and other representatives of this class of substances inhibit cell growth or cell division and are therefore used in the fight against cancer . The great interest in 10-deacetylbaccatin III is due to the difficulties in producing taxol and other taxanes in commercial quantities. Taxol can be obtained from the bark of the Pacific yew tree ( Taxus brevifolia ), a shrub-like tree that is native to northwest Canada and the USA and occurs there in scattered stands. Because the Pacific yew grows very slowly, the bark is only thick enough to extract taxol from trees that are around 100 years old. The taxol content in the bark is only about 0.01-0.02%. To obtain 1 g of taxol - this corresponds to only half the amount that is required for a patient in a typical treatment cycle - the bark of three fully grown trees is therefore necessary. The extraction of taxol from the bark of the Pacific yew tree leads to the destruction of the tree; 13,000 trees had to be felled for the first clinical trials with taxol alone. Calculations showed that the commercialization of Taxol with only yew bark as a source would have led to the complete extinction of the yew tree in a few years. In contrast, 10-deacetylbaccatin is a more sustainable source of taxane-based drugs: it is also found in significantly higher quantities of up to 0.2% in other types of yew (for example in the European yew ) and is not only contained in the bark, but can be obtained from regrowing needles and twigs while protecting the yew population.

Presentation and use

10-deacetylbaccatin from needles and branches of various species of yew by extraction obtained. The compound can be converted to Taxol in just a few steps. The anti-tumor agent cabazitaxel is also semi-synthetically accessible from 10-deacetylbaccatin III .

proof

To prove the connection can u. a. immunological detection methods are used.

Individual evidence

1. ↑ ^{a b c} Entry on 10-Deacetylbaccatin III at ChemicalBook , accessed January 30, 2011.
2. ↑ U.S. Patent 5,736,366, accessed January 30, 2011
3. ↑ informaworld.com: Co-solvent-Modified Supercritical Carbon Dioxide Extraction of 10-Deacetylbaccatin III from Needles of Taxus baccata L , accessed on January 30, 2011.
4. ↑ Data sheet 10-Deacetylbaccatin III from Taxus baccata at Sigma-Aldrich , accessed on May 9, 2016 ( PDF ).
5. ^ ^{A b} Paul M. Dewick: "Medicinal Natural Products: A Biosynthetic Approach", 3rd edition, Wiley 2009, pp. 226-227 ( limited preview in Google book search).
6. ^ Frank Petersen, René Amstutz: Natural Compounds as Drugs . Springer, 2008, ISBN 3-7643-8594-4 , pp. 103 ( limited preview in Google Book search).
7. ^ University of Southern Maine Online Chemistry Resources, accessed January 30, 2011 ( August 10, 2010 memento on the Internet Archive )
8. ↑ Immunological detection and quantitation of 10-deacetylbaccatin III in Taxus sp. plant and tissue cultures ; PMID 8060537 .