1396259-15-6

Basic information

• Product Name: (R)-3,8,9,10-tetrahydroxy-6-methyl-3,4-dihydroanthracen-1(2H)-one
• Synonyms: (R)-3,8,9,10-tetrahydroxy-6-methyl-3,4-dihydroanthracen-1(2H)-one
• CAS NO: 1396259-15-6
• Molecular Weight: 274.273
• Mol File: 1396259-15-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R)-3,8,9,10-tetrahydroxy-6-methyl-3,4-dihydroanthracen-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3,8,9,10-tetrahydroxy-6-methyl-3,4-dihydroanthracen-1(2H)-one(1396259-15-6)
• EPA Substance Registry System: (R)-3,8,9,10-tetrahydroxy-6-methyl-3,4-dihydroanthracen-1(2H)-one(1396259-15-6)

Safety Data

• Hazardous Substances Data: 1396259-15-6(Hazardous Substances Data)

Upstream product

• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 

Downstream Products

• 481-74-3 Chrysophanol 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 39546-16-2 (?)-flavoskyrin 

Relevant articles and documents

New Insights into the Conversion of Versicolorin A in the Biosynthesis of Aflatoxin B1

A crucial and enigmatic step in the complex biosynthesis of aflatoxin B1 is the oxidative rearrangement of versicolorin A to demethylsterigmatocystin. This step is thought to proceed by an oxidation-reduction-oxidation sequence, in which the NADPH-dependent oxidoreductase AflM catalyzes the enclosed reduction step. AflM from Aspergillus parasiticus, after heterologous production in E. coli and purification, however, catalyzed the reduction of the hydroquinoid form of the starting compound versicolorin A (25% conversion) to a so far unknown product of aflatoxin biosynthesis. The asymmetric reduction of emodin hydroquinone to (R)-3,8,9,10-tetrahydroxy-6-methyl-3,4-dihydroanthracen-1(2H)-one (up to 82% for AflM) has also been observed in previous studies using MdpC from Aspergillus nidulans (monodictyphenone biosynthetic gene cluster). The first (nonenzymatic) reduction of emodin to emodin hydroquinone, for example with sodium dithionite, is obligatory for the enzymatic reduction by AflM or MdpC. These results imply an unprecedented role of AflM in the complex enzymatic network of aflatoxin biosynthesis.

Promiscuity of an unrelated anthrol reductase ofTalaromyces islandicusWF-38-12

An anthrol reductase ofTalaromyces islandicusWF-38-12 (ARti-2) from an unrelated biosynthetic gene cluster (BGC) has been identified and characterized. It catalyses the NADPH-dependent reduction of anthrols (hydroanthraquinones), estrone and a naphthol with high stereo- and regioselectivity. The role of ARti-2, theCRG89872.1gene of the same BGC and non-enzymatic oxidation in the biosynthesis of (?)-flavoskyrin has been proposed.