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Cephalomannine

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-C4002

  • Specification : 98%(HPLC)

  • CAS number : 71610-00-9

  • Formula : C45H53NO14

  • Molecular Weight : 831.9

  • PUBCHEM ID : 6436208

  • Volume : 25mg

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Catalogue Number

BF-C4002

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

831.9

Appearance

White crystalline powder

Botanical Source

Taxus wallichiana var. mairei,Taxus cuspidata,Taxus wallichiana

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC=C(C)C(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O

Synonyms

Paclitaxel Related CoMpound A/(2α,5β,7β,10β,13α)-4,10-Diacetoxy-1,7-dihydroxy-13-{[(2R,3S)-2-hydroxy-3-{[(2E)-2-methylbut-2-enoyl]amino}-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl benzoate/Benzenepropanoic acid, α-hydroxy-β-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]amino]-, (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-dodecah ydro-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, (αR,βS)-/benzenepropanoic acid, α-hydroxy-β-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]amino]-, (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, (αR,βS)-/chephalomannine/(2α,5β,7β,10β,13α)-4,10-Diacetoxy-1,7-dihydroxy-13-{[(2R,3S)-2-hydroxy-3-{[(2E)-2-methyl-2-butenoyl]amino}-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl benzoate/3'-N-(trans-2-methyl-2-butenoyl)-3'-N-debenzoylpaclitaxel/CEPHALOMANNINE:BENZENEPROPANOICACID,-HYDROXY--[(2-METHYL-1-OXO-2-BUTENYL)AMINO]-,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]OX.../caphalomannine/Paclitaxel Related Compound A (20 mg) (Ce-phalomannine)/(2α,5β,7β,10β,13α)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-{[(2R,3S)-2-hydroxy-3-{[(2E)-2-methylbut-2-enoyl]amino}-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl benzoate/TAXOL B/CEPHALOMANNINE:BENZENEPROPANOICACID,-HYDROXY--[(2-METHYL-1-OXO-2-BUTENYL)AMINO]-,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/CEPHALOMANNINE (TAXOL B)/CEPHALOMANNINE(P)

IUPAC Name

[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

Applications

Cephalomannine is a taxol derivative with antitumor, antiproliferative properties. IC50 value:Target: Cephalomannine is an active anti-cancer agent obtained from Taxus yunnanensis and has an antineoplastic effect on tumors found in mice. Cephalomannine is a chemotherapy drug that is given as a treatment for some types of cancer. Cephalomannine is most commonly used to treat non-small cell lung cancer.

Density

1.4±0.1 g/cm3

Solubility

Methanol

Flash Point

516.0±34.3 °C

Boiling Point

929.5±65.0 °C at 760 mmHg

Melting Point

139-141ºC

InChl

InChI=1S/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33-,34+,35+,36?,38-,43+,44-,45+/m0/s1

InChl Key

DBXFAPJCZABTDR-UJLUYDJNSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:71610-00-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29883074

Abstract

An ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS-MS) method was developed to elucidate the impurity profiles of paclitaxel and paclitaxel injections from different Chinese pharmaceutical companies. The fragmentation patterns for paclitaxel and the related impurities were analyzed and summarized. To remove the interference from auxiliary materials, such as hydrogenated castor oil, paclitaxel was dissolved in ethanol for acid, base, peroxide, and light induced forced degradation analysis, which could produce all the impurities exist in the paclitaxel injection. A total of 10 impurities were characterized, such as cephalomannine (1), 7-epi-10-deacetylpaclitaxel (2), 7-epipaclitaxel (3), baccatin Ⅲ (4), ethyl ester side chain (5), 7-epi-baccatin Ⅲ (6), 10-deacetylpaclitaxel (7), paclitaxel isomer(C3-C11 bridge) (8), paclitaxel isomer (9), and N-benzoyl-(2R,3S)-3-phenylisoserine (10), respectively. Among them, compounds 1-3 could be introduced during manufacture processing. In the forced degradation studies, while acid induced degradation products included 3-7, base induced degradation could produce 2-7 and 10; while 7 is the main compound produced by hydrogen peroxide treatment, 4 compounds (3-5 and 7) were produced by high temperature environment and 5 compounds (2-5 and 9 which is the first reported) from intensity light exposure. Furthermore, 8 was the main impurity came from intensity light exposed paclitaxel powder. The results from this study provide an important reference in processing, optimization, quality control and evaluation of paclitaxel.

Title

[The impurity profiling of paclitaxel and its injection by UPLC-MS/MS].

Author

Zhang CY, Li J, Gao JM, Zhang QM, Shi YQ

Publish date

2016 Jun

PMID

26091963

Abstract

The response of two Taxus cell systems to the action of cyclodextrin (CD) and coronatine (CORO), supplied to the culture medium either separately or together, was studied. Two-stage Taxus globosa and Taxus media cell cultures were established and the elicitors were added at the beginning of the second stage. Growth, taxane production, and the expression of known taxol biosynthetic genes, including the recently characterized CoA ligase gene, were studied. Although CORO reduced the growth capacity of both cell lines, CD apparently counteracted this negative effect. Taxane production was significantly enhanced by the simultaneous addition of CD and CORO to the medium. The total taxane production in the T. media cell line was more than double that of T. globosa, but in the latter more than 90% of the taxanes produced were excreted to the medium. Individual taxane patterns also differed: at the height of production, the main taxanes in T. globosa cultures were cephalomannine and 10-deacetyltaxol, and in T. media, taxol and baccatin III. The low transcript levels of taxane biosynthetic genes found in T. globosa cells mirrored the lower taxane production in these cultures, while a high expression was strongly correlated with a high taxane production in T. media.

Copyright © 2015 Elsevier Ltd. All rights reserved.

KEYWORDS

Plant cell cultures; Taxanes; Taxol; Taxus globosa; Taxus×media; Transcription profiles

Title

Changes in gene transcription and taxane production in elicited cell cultures of Taxus × media and Taxus globosa.

Author

Ramirez-Estrada K1, Osuna L2, Moyano E3, Bonfill M1, Tapia N2, Cusido RM1, Palazon J4.

Publish date

2015 Sep

PMID

25645339

Abstract

A rapid, sensitive and reliable method has been developed and validated for the simultaneous determination of seven taxoids including 10-deacetylbaccatin III (10-DAB III), baccatin III, 5-epi-canadensene, taxinine M, 10-deacetyltaxol (10-DAT), cephalomannine and paclitaxel in rat plasma using docetaxel as the internal standard (IS). The plasma samples were pretreated by liquid-liquid extraction with methyl tert-butyl ether. The chromatographic separation was achieved on a C18 column (50 mm × 2.1 mm, 1.8 μm, Waters, USA) with a gradient elution program consisting of methanol and water (containing 0.1% formic acid) at a flow rate of 0.2 mL/min. Detection was performed under the selected reaction monitoring (SRM) scan using an electrospray ionization (ESI) in the positive ion mode. The mass transitions were as follows: m/z 567.4→444.9 for 10-DAB III, m/z 609.0→549.3 for baccatin III, m/z 617.4→496.9 for 5-epi-canadensene, m/z 709.6→649.3 for taxinine M, m/z 834.8→307.9 for 10-DAT, m/z 854.5→285.4 for cephalomannine, m/z 876.8→307.3 for paclitaxel and m/z 830.8→549.6 for IS, respectively. All calibration curves exhibited good linearity (r(2)>0.99) over a wide concentration range for all components. The intra-day and inter-day precisions at three different levels were both less than 14.3% in terms of relative standard deviation (RSD) and the accuracies ranged from -8.3% to 14.8% in terms of relative error (RE). The extraction recoveries of the seven compounds ranged from 62.5% to 100.5%. The developed method was successfully applied to the pharmacokinetic study of the seven taxoids in rat plasma after oral administration of the crude extract of the twigs and leaves of Taxus yunnanensis.

Copyright © 2015 Elsevier B.V. All rights reserved

KEYWORDS

Pharmacokinetics; Plasma concentration; Taxoids; Taxus yunnanensis; UPLC-MS/MS

Title

Simultaneous determination of seven taxoids in rat plasma by UPLC-MS/MS and pharmacokinetic study after oral administration of Taxus yunnanensis extracts.

Author

Liu B1, Gou X1, Bai X1, Hou X1, Li D1, Zhong G1, Jin J2, Huang M3.

Publish date

2015 Mar 25