142292-63-5

Basic information

• Product Name: 1H-Naphtho[2,3-c]pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, trans-
• CAS NO: 142292-63-5
• Molecular Formula: C16H14O6
• Molecular Weight: 302.284
• Mol File: 142292-63-5.mol

Chemical Properties

• CAS DataBase Reference: 1H-Naphtho[2,3-c]pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Naphtho[2,3-c]pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, trans-(142292-63-5)
• EPA Substance Registry System: 1H-Naphtho[2,3-c]pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, trans-(142292-63-5)

Safety Data

• Hazardous Substances Data: 142292-63-5(Hazardous Substances Data)

Usage

Derivative of naphthalene

The compound is derived from naphthalene, which is a type of hydrocarbon with two fused benzene rings.

Belongs to the class of pyran compounds

Pyran compounds are a type of heterocyclic compound that contains an oxygen atom in a six-membered ring.

Trans configuration

The compound has a trans configuration, which means that the two substituents on the double bond are on opposite sides of the molecule.

Contains a hydroxy group

The compound has a hydroxy group (-OH) attached to it, which is a polar and hydrophilic functional group.

Contains a methyl group

The compound has a methyl group (-CH3) attached to it, which is a nonpolar and hydrophobic functional group.

19 carbon atoms

The compound has a relatively large molecular weight and consists of 19 carbon atoms.

Potential pharmaceutical and medicinal applications

The presence of the hydroxy and carboxylic acid functional groups makes the compound potentially useful in various pharmaceutical and medicinal applications.

Upstream product

• 29394-61-4 Kalafungin 
• 958730-34-2 6-deoxykalafungin 

Relevant articles and documents

Unveiling Two Consecutive Hydroxylations: Mechanisms of Aromatic Hydroxylations Catalyzed by Flavin-Dependent Monooxygenases for the Biosynthesis of Actinorhodin and Related Antibiotics

Flavin-dependent monooxygenases are ubiquitous in living systems and are classified into single- or two-component systems. Actinorhodin, produced by Streptomyces coelicolor, is a representative polycyclic polyketide that is hydroxylated through the action of the two-component ActVA-5/ActVB hydroxylase system. These homologous systems are widely distributed in bacteria, but their reaction mechanisms remain unclear. This in vitro investigation has provided chemical proof of two consecutive hydroxylations via hydroxynaphthalene intermediates involved in actinorhodin biosynthesis. The ActVA-5 oxygenase component catalyzed a stepwise dihydroxylation of the substrate, whereas the ActVB flavin reductase not only supplied a reduced cofactor, but also regulated the quinone–hydroquinone interconversion of an intermediate. Our study provides clues for understanding the general biosynthetic mechanisms of highly functionalized aromatic natural products with structural diversity.

Epoxyquinone formation catalyzed by a two-component flavin-dependent monooxygenase involved in biosynthesis of the antibiotic actinorhodin

The biosynthetic gene cluster of the aromatic polyketide antibiotic actinorhodin (ACT) in Streptomyces coelicolor A3(2) carries a pair of genes, actVA-ORF5 and actVB, that encode a two-component flavin-dependent monooxygenase (FMO). Our previous studies have demonstrated that the ActVA-ORF5/ActVB system functions as a quinone-forming C-6 oxygenase in ACT biosynthesis. Furthermore, we found that this enzyme system exhibits an additional oxygenation activity with dihydrokalafungin (DHK), a proposed intermediate in the ACT biosynthetic pathway, and generates two reaction products. These compounds were revealed to be monooxygenated derivatives of kalafungin, which is spontaneously formed through oxidative lactonization of DHK. Their absolute structures were elucidated from their NMR spectroscopic data and by computer modeling and X-ray crystallography as (5S,14R)-epoxykalafungin and (5R,14S)-epoxykalafungin, demonstrating an additional epoxyquinone-forming activity of the ActVA-ORF5/ActVB system in vitro.

Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins

The first, enantiospecific total syntheses of pyranonaphthoquinone antibiotics, nanaomycins D and A, and their enantiomers kalafungin and 4-deoxykalafunginic acid, are described by an 'enantiodivergent' strategy from a common optically active intermediate, (1S,3RS,4S)-3,4-dihydro-5,9,10-trimethoxy-1-methyl-1H-naphtho[2,3-c]pyr an-3,4-diol, which has been derived from L-rhamnose via condensation of 4-methoxy-3-(phenylsulfonyl)-1-(3H)-isobenzofuranone and methyl 3,4,6-trideoxy-α-L-glycero-hex-3-enopyranosid-2-ulose.