21401-21-8

Basic information

• Product Name: taxiphyllin
• Synonyms: taxiphyllin;(2R)-Taxiphyllin;(2R)-(β-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
• CAS NO: 21401-21-8
• Molecular Formula: C₁₄H₁₇NO₇
• Molecular Weight: 311.28728
• Mol File: 21401-21-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 586.7°Cat760mmHg
• Flash Point: 308.6°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 1.32E-14mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: taxiphyllin(CAS DataBase Reference)
• NIST Chemistry Reference: taxiphyllin(21401-21-8)
• EPA Substance Registry System: taxiphyllin(21401-21-8)

Safety Data

• Hazardous Substances Data: 21401-21-8(Hazardous Substances Data)

Usage

General Description

Taxiphyllin is a natural chemical compound found in the leaves and stems of plants from the genus Taxus. It is a type of taxane, which is a class of diterpenoid compounds with anti-cancer and anti-tumor properties. Taxiphyllin has been studied for its potential as an anti-cancer agent and has shown promising results in inhibiting the growth of various cancer cell lines. It works by disrupting microtubule dynamics, which are essential for cell division, leading to cell cycle arrest and ultimately apoptosis in cancer cells. Research on taxiphyllin continues to explore its potential as a therapeutic agent for cancer treatment.

InChI:InChI=1/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1

Upstream product

• 60996-21-6 (2R)-4-acetoxy-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)]-2-phenylacetonitrile 
• 118736-06-4 C₁₃H₁₇NO₃Si 
• 878-00-2 4-formylphenyl acetate 
• 29883-15-6 amygdalin 
• 67-56-1 methanol 

Relevant articles and documents

General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides

An effective method for the chemical synthesis of cyanogenic glucosides has been developed as demonstrated by the synthesis of dhurrin, taxiphyllin, prunasin, sambunigrin, heterodendrin, and epiheterodendrin. O-Trimethylsilylated cyanohydrins were prepared and subjected directly to glucosylation using a fully acetylated glucopyranosyl fluoride donor with boron trifluoride-diethyl etherate as promoter to afford a chromatographically separable epimeric mixture of the corresponding acetylated cyanogenic glucosides. The isolated epimers were deprotected using a triflic acid/MeOH/ion-exchange resin system without any epimerization of the cyanohydrin function. The method is stereocontrolled and provides an efficient approach to chemical synthesis of other naturally occurring cyanogenic glucosides including those with a more complex aglycone structure.

Catalytic degradation of amygdalin by extracellular enzymes from Aspergillus niger

Amygdalin is a controversial anti-tumor natural product that has been used as an alternative cancer drug for many years. The anti-tumor mechanism and metabolism of amygdalin have been the focus of many studies. However, previous studies by our group demonstrated that amygdalin itself has no anti-tumor activity, but rather the active ingredients were determined to be amygdalin degradation products. To screen novel drugs with anti-tumor activity, the extracellular enzymes from Aspergillus niger were used to degrade amygdalin. Within 4 h of the catalytic reaction at 37°, amygdalin was rapidly degraded into four products. The products were then extracted and purified by column chromatography. By comparing the HPLC chromatograms, 1H NMR, 13C NMR and MS data, the products were identified as mandelonitrile, prunasin, benzaldehyde and phenyl-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2- yloxy)-acetonitrile (PTMT), a novel hydroxyl derivative of prunasin. Furthermore, pharmacology studies of these compounds demonstrated that 10 mg/kg of PTMT significantly suppressed the growth of S-18 tumor cells within 11 days in a concentration-dependent manner.