71135-22-3

Basic information

• Product Name: tetracenomycin C
• Synonyms: tetracenomycin C;8-demethyltetracenomycin C
• CAS NO: 71135-22-3
• Molecular Formula: C₂₃H₂₀O₁₁
• Molecular Weight: 472.3983
• Mol File: 71135-22-3.mol

Chemical Properties

• Boiling Point: 793.2°C at 760 mmHg
• Flash Point: 276.8°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 1.59E-26mmHg at 25°C
• Refractive Index: 1.711
• CAS DataBase Reference: tetracenomycin C(CAS DataBase Reference)
• NIST Chemistry Reference: tetracenomycin C(71135-22-3)
• EPA Substance Registry System: tetracenomycin C(71135-22-3)

Safety Data

• Hazardous Substances Data: 71135-22-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tetracenomycin C is used as a pharmaceutical compound for its potential therapeutic properties. The presence of the phenolic hydroxyl group may confer specific biological activities, such as antioxidant or anti-inflammatory effects, which could be harnessed for the development of new drugs or treatments.
Used in Chemical Research:
In the field of chemical research, tetracenomycin C serves as a valuable subject for studying the structure-activity relationships of tetracene compounds. Understanding how the substitution of the methoxy group with a phenolic hydroxyl group affects the compound's properties can provide insights into the design of new molecules with tailored characteristics for various applications.
Used in Material Science:
Tetracenomycin C may also find applications in material science, particularly in the development of novel materials with unique optical, electronic, or mechanical properties. The phenolic hydroxyl group could potentially participate in hydrogen bonding or other interactions that influence the material's overall performance.

InChI:InChI=1/C23H20O11/c1-8-14-9(6-11(32-2)15(8)21(29)34-4)5-10-16(17(14)25)20(28)22(30)13(24)7-12(33-3)19(27)23(22,31)18(10)26/h5-7,19,25,27,30-31H,1-4H3/t19-,22-,23-/m1/s1

Upstream product

• 82277-62-1 tetracenomycin A2 

Downstream Products

• 133497-15-1 4-O-<4-O-Acetyl-2,6-dideoxy-2-iodo-3-O-(p-methoxybenzyl)-α-L-talo-hexopyranosyl>tetracenomycin C 

Relevant articles and documents

First Total Syntheses of Tetracenomycins C and X

The first total syntheses of tetracenomycins C and X were achieved, featuring 1) preparation of a hexasubstituted naphthonitrile oxide by successive benzyne cycloadditions and an oxidative ring-opening reaction; 2) a novel ortho-quinone mono-acetal as the A-ring unit; 3) construction of three contiguous stereogenic centers by an asymmetric benzoin cyclization, an isoxazole oxidation, and a stereoselective reduction.

Cloning, sequencing, and heterologous expression of the elmGHIJ genes involved in the biosynthesis of the polyketide antibiotic elloramycin from Streptomyces olivaceus Tue2353

Elloramycin A (1) belongs to a small family of naphthacenequinones characterized by a unique highly hydroxylated cyclohexenone moiety. A cosmid clone 16F4, harboring genes for the production of 1 from Streptomyces olivaceus Tue2353, has been previously isolated. DNA sequence analysis of a 3.2-kb fragment from 16F4 revealed four open reading frames - the elmGHIJ genes. Heterologous expressions of the elmGHI genes in either Escherichia coli or Streptomyces lividans, followed by biochemical characterizations of the ElmGHI proteins, established ElmG as tetracenomycin B2 oxygenase, ElmH as tetracenomycin F1 monooxygenase, and ElmI as tetracenomycin F2 cyclase. These results provide direct biochemical evidence for the hypothesis that the biosynthesis of 1 in S. olivaceus parallels that of tetracenomycin C (2) in Streptomyces glaucescens and support the notion that the biosynthesis of the highly hydroxylated cyclohexenone moiety in other polyketides most likely follows the same paradigm as the tetracenomycin B2 or A2 oxygenase.