5146-12-3

Basic information

• Product Name: 2,3,4,5-tetrahydroxy-6-oxo-6H-benzo[7]annulene-8-carboxylic acid
• Synonyms: 2,3,4,6-Tetrahydroxy-5-oxo-5H-benzo[7]annulene-8-carboxylic acid; 5H-benzocycloheptene-8-carboxylic acid, 2,3,4,6-tetrahydroxy-5-oxo-
• CAS NO: 5146-12-3
• Molecular Formula: C₁₂H₈O₇
• Molecular Weight: 264.1877
• Mol File: 5146-12-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 327.3°C at 760 mmHg
• Flash Point: 166°C
• Density: 1.93g/cm³
• Vapor Pressure: 1.54E-05mmHg at 25°C
• Refractive Index: 1.819
• CAS DataBase Reference: 2,3,4,5-tetrahydroxy-6-oxo-6H-benzo[7]annulene-8-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-tetrahydroxy-6-oxo-6H-benzo[7]annulene-8-carboxylic acid(5146-12-3)
• EPA Substance Registry System: 2,3,4,5-tetrahydroxy-6-oxo-6H-benzo[7]annulene-8-carboxylic acid(5146-12-3)

Safety Data

• Hazardous Substances Data: 5146-12-3(Hazardous Substances Data)

Usage

Molecular structure

A complex structure containing a benzene ring fused with seven carbon atoms.

Functional groups

Four hydroxyl (-OH) groups and a carboxylic acid (-COOH) group attached at various positions on the ring.

Benzene ring

A central benzene ring with seven carbon atoms, which is a characteristic feature of this compound.

Derivative of benzoic acid

This compound is derived from benzoic acid, a simple aromatic carboxylic acid.

Aromatic carboxylic acid

It belongs to the class of aromatic carboxylic acids, which have a benzene ring attached to a carboxyl group.

Organic synthesis

2,3,4,5-tetrahydroxy-6-oxo-6H-benzo[7]annulene-8-carboxylic acid is commonly used in organic synthesis due to its unique structure.

Pharmaceutical research

The compound is also used in pharmaceutical research because of its potential medicinal properties.

Aromatic nature

The presence of the benzene ring gives the compound its aromatic nature, which influences its chemical properties and reactivity.

Valuable precursor

The compound's various functional groups make it a valuable precursor for the synthesis of other organic compounds.

Upstream product

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 2596-50-1 (-)-epigallocathechin gallate 
• 7732-18-5 water 
• 87-66-1 2-hydroxyresorcinol 
• 863-03-6 (-)-epicatechin gallate 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 154-23-4 catechin 
• 102067-92-5 epitheaflagallin 3-O-gallate 

Downstream Products

• 569-77-7 purpurogallin 

Relevant articles and documents

Virtual screening of National Cancer Institute database for claudin-4 inhibitors: Synthesis, biological evaluation, and molecular dynamics studies

Claudin-4 (CLDN4) is a vital member of tight-junction proteins that is often overexpressed in cancer and other malignancies. The three-dimensional structure of human CLDN4 was constructed based on homology modeling approach. A total of 265 242 molecules from the National Cancer Institute (NCI) database has been utilized as a dataset for this study. In the present work, structure-based virtual screening is performed with the NCI database using Glide. By molecular docking, 10 candidate molecules with high scoring functions, which binds to the active site of CLDN4 were identified. Subsequently, molecular dynamics simulations of membrane protein were used for optimization of the top-three lead compounds (NCI110039, NCI344682, and NCI661251) with CLDN4 in a dynamic system. The lead molecule from NCI database NCI11039 (purpurogallin carboxylic acid) was synthesized and cytotoxic properties were evaluated with A549, MCF7 cell lines. Our docking and dynamics simulations predicted that ARG31, ASN142, ASP146, and ARG158 as critically important residues involved in the CLDN4 activity. Finally, three lead candidates from the NCI database were identified as potent CLDN4 inhibitors. Cytotoxicity assays had proved that purpurogallin carboxylic acid had an inhibitory effect towards breast (MCF7) and lung (A549) cancer cell lines. Computational insights and in vitro (cytotoxicity) studies reported in this study are expected to be helpful for the development of novel anticancer agents.

Benzotropolone derivatives and modulation of inflammatory response

The present invention provides novel benzotropolone derivatives represented by the general formula: 1 including neotheaflavate B and EGCGCa. The benzotropolone derivatives of the present invention are effective antioxidant and anti-inflammatory agents. The present invention also provides novel method of synthesizing benzotropolone compounds in high yields and method of treating inflammatory conditions using benzotropolone containing compounds.

Tannins and related compounds. XXXVI. Isolation and structures of theaflagallins, new red pigments from black tea

-