• 10-Deacetyl Baccatin III packaged and labeled.

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SKU: D002

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Description

10-Deacetyl Baccatin III (syn: 10-DAB) is a natural organic compound produced by the Pacific Yew tree.  It is used as a key backbone intermediate for the semi-synthesis of Paclitaxel (Taxol), an anti-cancer drug and Docetaxel and their analogs. It is used to study the biosynthetic pathway of Taxol.  The trunk and leaves contain the highest concentration of 10-Deacetyl Baccatin III, but it may be found in parts of the Yew tree.

    CAS Number

    32981-86-5

    Molecular Formula

    C29H36O10

    Molecular Weight

    544.59

    Mechanism of Action

    Paclitaxel (Taxol) has a unique mode of action involving abnormal polymerization of tubulin and disruption of mitosis.

    Storage Conditions

    2-8 °C

    Tariff Code

    2932.99.6100

Applications

    Cancer Applications

    10-Deacetyl Baccatin III is commonly used as an intermediate in the synthesis of paclitaxel (Taxol), an anti-cancer drug.

    Plant Biology Applications

    Taxus cell culture may be an alternate source of Paclitaxel, and significantly increased amounts of Paclitaxel were observed after exposure to methyl jasmonate (Yukimune et al, 1996).

Specifications

    Form

    Powder

    Appearance

    White or off-White Powder

    Source

    Taxus Baccata

    Loss on Drying

    ≤3.0%

References

    References

    Gelderblom H et al (1999)  Disposition of [G-(3)H]paclitaxel and cremophor EL in a patient with severely impaired renal function. Drug Metab Dispos. 27(11):1300-1305  PMID 10534315

    Gueritte-Voegelein F, Senih V, David B, Guenard D and Potier P (1986)  Chemical studies of 10-deacetyl baccatin III: Hemisynthesis of taxol derivatives. Tetrahed. 42(16):4451-4460

    Kant J et al (1994)  A chemoselective approach to functionalize the C-10 position of 10-deacetylbaccatin III. Synthesis and biological properties of novel C-10 Taxol® analogues. Tetrahed. Lett. 35(31):5543-5546

    Ojima I et al (1997)  Syntheses and structure-activity relationships of toxoids derived from 14 beta-hydroxy-10-deacetylbaccatin III. J. Med. Chem. 40(3):267-278  PMID 9022793

    Yukimune Y, Tabata H, Higashi Y and Hara Y (1996)  Methyl jasmonate-induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures. Nature Biotechnol. 14(9):1129-1132

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