Skip to Content
MilliporeSigma
All Photos(1)

Documents

Y0000700

Paclitaxel natural for peak identification

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Paclitaxel

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C47H51NO14
CAS Number:
33069-62-4
Molecular Weight:
853.91
Beilstein/REAXYS Number:
1420457
MDL number:
MFCD00869953
UNSPSC Code:
41116107
PubChem Substance ID:
329831103
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

paclitaxel

manufacturer/tradename

EDQM

mp

213 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)c5ccccc5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7

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

InChI key

RCINICONZNJXQF-MZXODVADSA-N

Gene Information

human ... TUBA1A(7846) , TUBA1B(10376) , TUBA1C(84790) , TUBA3C(7278) , TUBA3E(112714) , TUBA4A(7277) , TUBB(203068) , TUBB1(81027) , TUBB2A(7280) , TUBB2B(347733) , TUBB3(10381) , TUBB4A(10382) , TUBB4B(10383) , TUBB6(84617) , TUBB8(347688)

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Paclitaxel natural for peak identification EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Caution

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Other Notes

Sales restrictions may apply.

related product

Product No.
Description
Pricing

1720000

Xanthanoic acid, United States Pharmacopeia (USP) Reference Standard

Y0000698

Paclitaxel, European Pharmacopoeia (EP) Reference Standard

Y0000719

Paclitaxel semi-synthetic for peak identification, European Pharmacopoeia (EP) Reference Standard

Y0000739

Paclitaxel semi-synthetic for system suitability, European Pharmacopoeia (EP) Reference Standard

Y0000699

Paclitaxel impurity C, European Pharmacopoeia (EP) Reference Standard

1491332

Paclitaxel, United States Pharmacopeia (USP) Reference Standard

1491354

Paclitaxel Related Compound B, United States Pharmacopeia (USP) Reference Standard

1491343

Paclitaxel Related Compound A, United States Pharmacopeia (USP) Reference Standard

1491365

Paclitaxel impurity mixture, United States Pharmacopeia (USP) Reference Standard

PHR1803

Paclitaxel, Pharmaceutical Secondary Standard; Certified Reference Material

01517

N-Cinnamoyl-N-debenzoylpaclitaxel, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

95185

N-Debenzoyl-N-(phenylacetyl)paclitaxel, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

29914

10-O-Deacetylpaclitaxel, reference material

PHR2112

Paclitaxel Related Compound B, Pharmaceutical Secondary Standard; Certified Reference Material

PHR9146

7-O-Acetylpaclitaxel, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

PHR9149

7-epi-Paclitaxel, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

PHR9150

Paclitaxel impurity K, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

PHR2111

Paclitaxel Related Compound A, Pharmaceutical Secondary Standard; Certified Reference Material

PHR3007

10-desacetyl-baccatin III, pharmaceutical secondary standard, certified reference material

PHR3261

Xanthanoic Acid, pharmaceutical secondary standard, certified reference material

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Muta. 2 - Repr. 1B - STOT RE 1

target_organs

Central nervous system,Bone marrow,Cardio-vascular system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Sorry, we don't have COAs for this product available online at this time.

If you need assistance, please contact Customer Support.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

Taxol phyproof® Reference Substance

PHL89806

Taxol

Paclitaxel, Taxus sp. Antitumor and antileukemic agent isolated from the bark of the yew tree.

Sigma-Aldrich

580555

Paclitaxel, Taxus sp.

Docetaxel purum, ≥97.0% (HPLC)

Sigma-Aldrich

01885

Docetaxel

Taroh Satoh et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 32(19), 2039-2049 (2014-05-29)
In Asian countries, paclitaxel once per week is used as second-line treatment in advanced gastric cancer, including human epidermal growth factor receptor 2 (HER2) -positive tumors. The role of anti-HER2 agents, including lapatinib, in this setting and population is unclear.
Erica Gornstein et al.
Neuropharmacology, 76 Pt A, 175-183 (2013-08-28)
Paclitaxel is a microtubule-binding compound that is widely used as a chemotherapeutic in the treatment of common cancers, including breast and ovarian cancer. Paclitaxel binding along the length of microtubules stabilizes them and suppresses their dynamics, leading to mitotic arrest
Zhiping Zhang et al.
Expert opinion on drug delivery, 10(3), 325-340 (2013-01-08)
Paclitaxel (PTX) is one of the most effective broad-spectrum chemotherapeutic agents in the treatment of cancers. However, its clinical application has been limited due to its poor water solubility. Its current clinical administration uses the adjuvant of serious side effects
Guido Bocci et al.
Angiogenesis, 16(3), 481-492 (2013-02-08)
In the mid 1990s, researchers began to investigate the antiangiogenic activity of paclitaxel as a possible additional mechanism contributing to its antineoplastic activity in vivo. In the last decade, a number of studies showed that paclitaxel has antiangiogenic activity that
Bradley J Monk et al.
The Lancet. Oncology, 15(8), 799-808 (2014-06-22)
Angiogenesis is a valid target in the treatment of epithelial ovarian cancer. Trebananib inhibits the binding of angiopoietins 1 and 2 to the Tie2 receptor, and thereby inhibits angiogenesis. We aimed to assess whether the addition of trebananib to single-agent
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service