Gentisein

Base Information

• Chemical Name: Gentisein
• CAS No.: 529-49-7
• Molecular Formula: C13H8 O5
• Molecular Weight: 244.204
• Hs Code.: 2932999099
• UNII: 0P3G42TQ63
• ChEMBL ID: CHEMBL361025
• DSSTox Substance ID: DTXSID20200944
• Metabolomics Workbench ID: 43860
• Nikkaji Number: J11.878H
• NSC Number: 329491
• Wikidata: Q27106719
• Mol file: 529-49-7.mol

Synonyms:1,3,7-trihydroxy-xanthone;1,3,7-trihydroxyxanthone;gentisein

Chemical Property of Gentisein

Chemical Property:

• Vapor Pressure: 4.62E-13mmHg at 25°C
• Boiling Point: 558.1°Cat760mmHg
• Flash Point: 224.7°C
• PSA: 90.90000
• Density: 1.64g/cm³
• LogP: 2.06300
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 244.03717335
• Heavy Atom Count: 18
• Complexity: 344

Purity/Quality:

99% ^*data from raw suppliers

Gentisein(NSC329491) 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)C(=O)C3=C(C=C(C=C3O2)O)O
• General Description: Gentisein (1,3,7-trihydroxyxanthone) is a xanthone derivative that serves as a key intermediate in the synthesis of natural products such as osajaxanthone and nigrolineaxanthone F. It can be efficiently synthesized through a five-step process from 1,3,5-trimethoxybenzene, achieving high yields (62%). Its regioselective coupling with prenal under varying conditions enables the exclusive production of osajaxanthone (75% yield) or nigrolineaxanthone F (98% yield), demonstrating its utility as a versatile precursor in xanthone synthesis with improved efficiency and selectivity over prior methods.

Technology Process of Gentisein

There total 21 articles about Gentisein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

3,5-dihydroxyphenol (108-73-6) + 2,5-dihydroxybenzoic acid. (490-79-9) → gentitein (529-49-7)

Guidance literature:

With tin(ll) chloride; at 140 ℃; for 0.0138889h; regioselective reaction; Microwave irradiation;

DOI:10.1016/j.bmc.2012.03.074

Reference yield: 82.0%

7-hydroxy-1,3-dimethoxy-9H-xanthen-9-one (39838-86-3) → gentitein (529-49-7)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo0606655

Reference yield: 77.2%

2,5-dihydroxybenzoic acid. (490-79-9) + recorcinol (108-46-3) → gentitein (529-49-7)

Guidance literature:

With zinc(II) chloride; trichlorophosphate; at 75 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.ejmech.2017.03.068

upstream raw materials:

3,5-dimethoxyphenol

5-methoxysalicylic acid

2,5-dihydroxybenzoic acid.

isogentisine

Downstream raw materials:

1-hydroxy-3,7-dimethoxyxanthone

1,3,7-Trimethoxyxanthon

gentisin

osajaxanthone

Refernces

Facile synthesis of 1,3,7-trihydroxyxanthone and its regioselective coupling reactions with prenal: Simple and efficient access to osajaxanthone and nigrolineaxanthone F

10.1021/jo0606655

The research aims to develop a simple and efficient method for synthesizing 1,3,7-trihydroxyxanthone and its subsequent regioselective coupling reactions with prenal to exclusively produce the natural products osajaxanthone and nigrolineaxanthone F. The study describes a five-step synthesis of 1,3,7-trihydroxyxanthone starting from 1,3,5-trimethoxybenzene, involving NBS-induced bromination, lithiation, benzoylation, selective deprotection, intramolecular cyclization, and demethylation, achieving an overall yield of 62%. The regioselective coupling reactions with prenal were conducted under different conditions: at room temperature with calcium hydroxide yielding osajaxanthone (75% yield) and under thermal conditions at 140-150 °C yielding nigrolineaxanthone F (98% yield). The study concludes that this approach offers a straightforward and efficient route to these xanthones, with high yields and selectivity, providing a significant improvement over previous methods. The structures of the compounds were confirmed using analytical and spectral data, including X-ray crystallography.