60696-52-8

Basic information

• Product Name: Asterriquinone
• Synonyms: Asterriquinone
• CAS NO: 60696-52-8
• Molecular Formula: C32H30N2O4
• Molecular Weight: 506.599
• Mol File: 60696-52-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 726.2°C at 760 mmHg
• Flash Point: 393°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 3.92E-22mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: Asterriquinone(CAS DataBase Reference)
• NIST Chemistry Reference: Asterriquinone(60696-52-8)
• EPA Substance Registry System: Asterriquinone(60696-52-8)

Safety Data

• Hazardous Substances Data: 60696-52-8(Hazardous Substances Data)

Usage

Occurrence

Aspergillus terreus var. africanus elaborates a number of closely related alkaloidal metabolites which have been separated and purified by chromatography. This component crystallizes well from MeOH.

InChI:InChI=1/C32H30N2O4/c1-7-31(3,4)33-17-21(19-13-9-11-15-23(19)33)25-27(35)29(37)26(30(38)28(25)36)22-18-34(32(5,6)8-2)24-16-12-10-14-20(22)24/h7-18,35,38H,1-2H2,3-6H3

Upstream product

• 1001099-63-3 2,5-dichloro-3,6-bis(1-(2-methylbut-3-en-2-yl)-1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione 
• 26361-18-2 2,5-dibromo-3,6-diethoxy-1,4-benzoquinone 
• 477883-73-1 2,5-bis[1-(1,1-dimethylallyl)-1H-indol-3-yl]-3,6-diethoxy-[1,4]benzoquinone 
• 160786-85-6 2,5-bis<1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl>-3-acetoxy-6-hydroxy-2,5-cyclohexadiene-1,4-dione 
• 60924-75-6 asterriquinone dimethyl ether 

Downstream Products

• 60924-75-6 asterriquinone dimethyl ether 

Relevant articles and documents

Four new metabolites of Aspergillus terreus

Four new metabolites (1-4) were isolated from mycelium of Aspergillus terreus IFO 6123 producing asterriquinone (ARQ). The structures of 1 and 2 were shown to be 3,6-bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-furo[3,2-b]furan-2, 5-dione (asterridinone) and 2,5-bis[1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3-acetoxy-6-hydroxy-2, 5-cyclohexadiene-1,4-dione (ARQ monoacetate), respectively, by the chemical and spectral data. Compounds 3 and 4 were identified with known asterriquinone isomers, 2-[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-5-[2-(3-methyl-2-butenyl )-1H-indol-3-yl]-3,6-dihydroxy-2,5-cyclohexadiene-1,4-dione (isoARQ) and 2,5-bis[2-(3-methyl-2-butenyl)-1H-indol-3-yl]-3,6-dihydroxy-2,5-cycloh exadiene-1,4-dione (neoARQ), respectively.

Total syntheses of demethylasterriquinone B1, an orally active insulin mimetic, and demethylasterriquinone A1.

Two total syntheses of the unsymmetrical bis-indolylquinone natural product demethylasterriquinone B1 (also known as L-783,281) have been accomplished. The first exploits a known base-promoted condensation of indoles with bromanil, which stops at monoaddition using the sterically hindered 2-isoprenylindole. This permits addition of the second indole, 7-prenylindole, which gives both meta- and para-substituted bis-indolylquinone products. This regiochemical control problem was solved by extension of a method we recently developed for acid-promoted addition of indoles to 2,5-dichlorobenzoquinone. Under our original mineral acid conditions, reaction of 2-isoprenylindole with dichlorobenzoquinone fails, but it succeeds with 3-bromo-2,5-dichlorobenzoquinone using acetic acid as the promoter. The regiochemistry established in such selectively bromine-substituted quinones can be exploited in Stille couplings. As a model system, the synthesis of demethylasterriquinone A1 was accomplished using as the key step a Stille coupling of a 2,5-dibromobenzoquinone with an (N-isoprenylindol-3-yl)tin, producing the para-substituted bis-indolylquinone exclusively. Use of a (7-prenylindole)tin in coupling with a bromo-2,5-dichloro-4-indolylbenzoquinone gives the demethylasterriquinone B1 precursor. The dihaloquinone products of these indole/quinone coupling processes can be hydrolyzed to the dihydroxyquinone natural products. Demethylasterriquinone B1 is of high recent interest as a small molecule insulin mimetic with oral anti-diabetic activity in mice.

Metabolic products of Aspergillus terreus. IV. Metabolites of the strain IFO 8835. (2). The isolation and chemical structure of indolyl benzoquinone pigments

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