An internal standard for the quantification of paclitaxel
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Unlabeled Version(s)
10461Paclitaxel
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Paclitaxel-d5

Item No. 22092

Technical Information
Formal Name
βS-(benzoyl-2,3,4,5,6-d5-amino)-αR-hydroxy-benzenepropanoic acid, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester
CAS Number
1129540-33-5
Molecular Formula
C47H46D5NO14
Formula Weight
Purity
≥99% deuterated forms (d1-d5)
A solid
Chloroform: Slightly SolubleMethanol: Slightly Soluble
SMILES
O=C([C@H](OC(C)=O)C1=C(C)[C@@H](OC([C@H](O)[C@@H](NC(C2=C([2H])C([2H])=C([2H])C([2H])=C2[2H])=O)C3=CC=CC=C3)=O)C[C@]([C@H]4OC(C5=CC=CC=C5)=O)(O)C1(C)C)[C@@]6(C)[C@@]4([H])[C@@]7(OC(C)=O)[C@H](OC7)C[C@@H]6O
InChi Code
InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1/i8D,12D,13D,18D,19D
InChi Key
RCINICONZNJXQF-JQTCHTAZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Paclitaxel-d5 contains five deuterium atoms. It is intended for use as an internal standard for the quantification of paclitaxel (Item No. 10461) using GC- or LC-MS. Paclitaxel is cytotoxic against a variety of cancer cell lines with IC50 values ranging from 2.5-7.5 nM.1 It disrupts multipolar spindle formation, inducing cell cycle arrest in various human cell cancer lines (IC50s = 6.7-18.5 nM) at both prophase and G1.2 It also initiates apoptosis of cancer cells through multiple mechanisms involving p53-dependent and -independent pathways, Bcl-2 family members, cyclin-dependent kinases, and c-Jun N-terminal kinases/stress-activated protein kinases.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Liebmann, J.E., Cook, J.A., Lipschultz, C., et alCytotoxic studies of paclitaxel (Taxol) in human tumour cell lines. Br. J. Cancer 68(6), 1104-1109 (1993).

    2. Woods, C.M., Zhu, J., McQueney, P.A., et alTaxol-induced mitotic block triggers rapid onset of a p53-independent apoptotic pathway. Mol. Med. 1(5), 506-526 (1995).

    3. Wang, T.h., Wang, H.S., and Soong, Y.K. Paclitaxel-induced cell death: Where the cell cycle and apoptosis come together. Cancer 88(11), 2619-2628 (2000).