479-05-0

Basic information

• Product Name: flaviolin
• Synonyms: flaviolin;2,5,7-Trihydroxy-1,4-naphthalenedione;2,5,7-Trihydroxy-1,4-naphthoquinone
• CAS NO: 479-05-0
• Molecular Formula: C10H6O5
• Molecular Weight: 206.15
• Mol File: 479-05-0.mol

Chemical Properties

• Melting Point: 250 °C (approx, decomp)(Solv: 1,4-dioxane (123-91-1))
• Boiling Point: 539.4°Cat760mmHg
• Flash Point: 294.1°C
• Appearance: /
• Density: 1.802g/cm³
• Vapor Pressure: 3.01E-12mmHg at 25°C
• Refractive Index: 1.785
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: flaviolin(CAS DataBase Reference)
• NIST Chemistry Reference: flaviolin(479-05-0)
• EPA Substance Registry System: flaviolin(479-05-0)

Safety Data

• Hazardous Substances Data: 479-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Flaviolin is used as a pharmaceutical compound for its potential therapeutic properties. It has been studied for its antioxidant, anti-inflammatory, and antimicrobial activities, which could make it a valuable component in the development of new drugs for various health conditions.
Used in Cosmetic Industry:
In the cosmetic industry, flaviolin may be used as an active ingredient in skincare products due to its antioxidant properties. It could help protect the skin from environmental damage, promote skin health, and potentially slow down the aging process.
Used in Research and Development:
Flaviolin is also used in research and development for its unique chemical structure and properties. Scientists may study its interactions with other compounds and explore its potential applications in various fields, such as materials science or biotechnology.

InChI:InChI=1/C10H6O5/c11-4-1-5-9(6(12)2-4)7(13)3-8(14)10(5)15/h1-3,11-13H

Upstream product

• 71741-18-9 6,8-Bis-benzyloxy-naphthalene-1,3-diol 
• 13586-04-4 3,6,8-trimethoxy-1-naphthol 
• 4724-10-1 methyl 2-(3,5-dihydroxyphenyl)acetate 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 126495-72-5 methyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 49598-85-8 scytalone 
• 4923-54-0 5,7-dihydroxy-1,4-naphthoquinone 
• 18512-30-6 1,3,6,8-Tetrahydroxynaphthalene 
• 5518-91-2 5-hydroxy-2,7-dimethoxy-1,4-naphthoquinone 
• 2732-96-9 3,5-dibenzyloxyphenylacetic acid 
• 80457-61-0 methanesulfonyl 3,5-dibenzyloxybenzyl alcohol 
• 65857-78-5 methyl 2-acetyl-3,5-bis(benzyloxy)phenylacetate 

Downstream Products

• 5518-91-2 5-hydroxy-2,7-dimethoxy-1,4-naphthoquinone 

Relevant articles and documents

Characterization of a fungal thioesterase having claisen cyclase and deacetylase activities in melanin biosynthesis

Melanins are a broad class of darkly pigmented macromolecules formed by oxidative polymerization of phenolic monomers. In fungi, melanins are known virulence factors that contribute to pathogenicity. Their biosynthesis generally involves polymerization of 1,8-dihydroxynaphthalene via a 1,3,6,8- tetrahydroxynaphthalene (THN) precursor assembled by multidomain, nonreducing polyketide synthases. Convergent routes to THN have evolved in fungi. Parallel heptaketide and hexaketide pathways exist that utilize conventional C-terminal thioesterase/Claisen cyclase domains and separate side-chain deacylases. Here, in vitro characterization of Pks1 from Colletotrichum lagenarium establishes a true THN synthase with a bifunctional thioesterase (TE) catalyzing both cyclization and deacetylation of an enzyme-bound hexaketide substrate. Chimeric TE domains were generated by swapping lid regions of active sites between classes of melanin TEs to gain insight into this unprecedented catalysis of carbon-carbon bond making and breaking by an α/β-hydrolase fold enzyme.

Exploiting the reaction flexibility of a type III polyketide synthase through in vitro pathway manipulation

A synthetic metabolic pathway has been constructed in vitro consisting of the type III polyketide synthase from Streptomyces coelicolor and peroxidases from soybean and Caldariomyces fumago (chloroperoxidase). This has resulted in the synthesis of the pentaketide flaviolin and its dimeric derivative, and a wide range of pyrones and their coupled derivatives with flaviolin, as well as their halogenated derivatives. The addition of acyl-CoA oxidase to the pathway prior to the polyketide synthase resulted in unsaturated pyrone side chains, further broadening the product spectrum that can be achieved. The approach developed in this work, therefore, provides a new model to exploit biocatalysis in the synthesis of complex natural product derivatives. Copyright

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.

DEOXYGENATION IN THE BIOSYNTHESIS OF POLYKETIDES: MECHANISM OF BIOMIMETIC REDUCTION OF TETRAHYDROXYNAPHTHALENE

A biomimetic synthesis of scytalone, a simple derivative of tetralone, was reinvestigeted using NMR spectroscopy.Scytalone was formed from 1,3,6,8-tetrahydroxynaphthalene (1,3,6,8-THN) by sodium borohydride reduction only in the presence of sodium methoxi

Synthesis of juglone derivatives. Hydroxy, acetyl and ethyl substituents

A number of hydroxyjuglones were prepared by the Thiele-Winter reaction onjuglone derivatives and by hydroxylation with ethanol-hydrochloric acid: 2-hydroxy, 3-hydroxy, 2,7-dihydroxy, 3,7-di-hydroxy, 6-acetyl-2-hydroxy, and 6-acetyl-3-hydroxyjuglone. By reductive acetylation of hydroxyjuglones, followed by Fries rearrangement and oxidative hydrolysis several acetyljuglones, and from them ethyljuglones by sodium borohydride reduction, were synthesized: 3-acetyl-2-hydroxy, 6-acetyl-2,3-dihydroxy, 6-acetyl-2,7-dihydroxy, and 6-acetyl-2,3,7-trihydroxyjuglone. Several of the newly synthesized compounds had previously been isolated from sea urchin spines.