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10-Deacetylbaccatin III

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-D2018

  • Specification : 98%

  • CAS number : 32981-86-5

  • Formula : C29H36O10

  • Molecular Weight : 544.59

  • PUBCHEM ID : 154272

  • Volume : 20mg

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Catalogue Number

BF-D2018

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

544.59

Appearance

White crystalline powder

Botanical Source

Taxus wallichiana var. chinensis,Taxus wallichiana

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)O

Synonyms

10-Dab/10-DAB (10-Deacetylbaccatin)/(2α,5β,7β,10α,13α)-4-Acetoxy-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate/(2α,5β,7β,10β,13α)-4-(acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate/10-Deacetylbaccatine/10-deacetylbaccatin11/10-DAB-III/10DBA III/10-Deacetyl/10-DEACETYLBACCATIN/10-Deacetylbaccatin-III/10-desacetylbaccatin III/10-Deacetylbaccatin III/DESACETYLBACCATINE/Docetaxel impurity E/7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one, 12b-(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-, (2aR,4S,4aS,6S,9S,11S,12S,12aR,12bS)-/(2α,5β,7β,10β,13α)-4-Acetoxy-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate/7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one, 12b-(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-

IUPAC Name

[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

Density

1.4±0.1 g/cm3

Solubility

Methanol

Flash Point

233.5±26.4 °C

Boiling Point

716.8±60.0 °C at 760 mmHg

Melting Point

231-236 °C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2922190000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:32981-86-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31783790

Abstract

Background
Trees of the genus Taxus are highly valuable medicinal plants with multiple pharmacological effects on various cancer treatments. Paclitaxel from Taxus trees is an efficient and widely used anticancer drug, however, the accumulation of taxoids and other active ingredients can vary greatly among Taxus species. In our study, the metabolomes of three Taxus species have been investigated.

Results
A total of 2246 metabolites assigned to various primary and secondary metabolic pathways were identified using an untargeted approach. Analysis of differentially accumulated metabolites identified 358 T. media-, 220 T. cuspidata-, and 169 T. mairei-specific accumulated metabolites, respectively. By searching the metabolite pool, 7 MEP pathway precursors, 11 intermediates, side chain products and derivatives of paclitaxel, and paclitaxel itself were detected. Most precursors, initiated intermediates were highly accumulated in T. mairei, and most intermediate products approaching the end point of taxol biosynthesis pathway were primarily accumulated in T. cuspidata and T. media. Our data suggested that there were higher-efficiency pathways to paclitaxel in T. cuspidata and T. media compared with in T. mairei. As an important class of active ingredients in Taxus trees, a majority of flavonoids were predominantly accumulated in T. mairei rather than T. media and T. cuspidata. The variations in several selected taxoids and flavonoids were confirmed using a targeted approach.

Conclusions
Systematic correlativity analysis identifies a number of metabolites associated with paclitaxel biosynthesis, suggesting a potential negative correlation between flavonoid metabolism and taxoid accumulation. Investigation of the variations in taxoids and other active ingredients will provide us with a deeper understanding of the interspecific differential accumulation of taxoids and an opportunity to accelerate the highest-yielding species breeding and resource utilization.

KEYWORDS

Metabolome, Interspecific differential accumulation, Systematic correlativity analysis, Taxoid, Taxus

Title

Comparative metabolomic analysis reveals the variations in taxoids and flavonoids among three Taxus species

Author

Ting Zhou,#1,2 Xiujun Luo,#1,3 Chengchao Zhang,1,3 Xinyun Xu,1,3 Chunna Yu,1,3 Zhifang Jiang,1,3 Lei Zhang,4 Huwei Yuan,5,6 Bingsong Zheng,5,6 Erxu Pi,corresponding author1 and Chenjia Shencorresponding author1,3

Publish date

2019 Nov 29

PMID

26903156

Abstract

Organocatalytic site-selective diversification of 10-deacetylbaccatin III, a key natural product for the semisynthesis of taxol, has been achieved. Various acyl groups were selectively introduced into the C(10)-OH of 10-deacetylbaccatin III. The C(10)-OH selective acylation was also applied to acylative site-selective dimerization of 10-deacetylbaccatin III to provide the structurally defined dimer.

Title

Organocatalytic Site-Selective Acylation of 10-Deacetylbaccatin III.

Author

Yanagi M1, Ninomiya R, Ueda Y, Furuta T, Yamada T, Sunazuka T, Kawabata T.

Publish date

2016 Jul 1


Description :

10-Deacetylbaccatin-III is an intermediate for taxol analog preparations. IC50 value:Target: Taxols have exhibit antitumor agents. Several of these taxols can be synthesized from 10- Deacetylbaccatin-III. 10-Deacetylbaccine III is the fifth intermediate of paclitaxel biosynthesis. The biosynthetic pathway consists of approximately 20 enzymatic steps but is not fully elucidated. 10-Deacetylbaccine III is an antineoplastic agent and an anti-cancer intermediate.