1013-69-0

Basic information

• Product Name: 2-Methyl-5,7-dihydroxychromone
• Synonyms: 2-Methyl-5,7-dihydroxy-4H-1-benzopyran-4-one;2-Methyl-5,7-dihydroxychromone;5,7-Dihydroxy-2-methyl-4H-1-benzopyran-4-one;Noreugenin;reugenin
• CAS NO: 1013-69-0
• Molecular Formula: C₁₀H₈O₄
• Molecular Weight: 192.1681
• Mol File: 1013-69-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 279 °C
• Boiling Point: 394.6 °C at 760 mmHg
• Flash Point: 164 °C
• Appearance: /
• Density: 1.456 g/cm³
• Vapor Pressure: 8.59E-07mmHg at 25°C
• Refractive Index: 1.651
• PKA: 6.58±0.40(Predicted)
• CAS DataBase Reference: 2-Methyl-5,7-dihydroxychromone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-5,7-dihydroxychromone(1013-69-0)
• EPA Substance Registry System: 2-Methyl-5,7-dihydroxychromone(1013-69-0)

Safety Data

• Hazardous Substances Data: 1013-69-0(Hazardous Substances Data)

Usage

General Description

2-Methyl-5,7-dihydroxychromone is a chemical compound that belongs to the family of flavones, which are commonly found naturally in various plant species. These are yellow pigments that provide coloration for some flowers, fruits, and leaves. The specific compound, 2-methyl-5,7-dihydroxychromone, exhibits antioxidant properties, which means it can help protect cells from damages caused by harmful molecules known as free radicals. Studies have also suggested that flavones like this one might have potential health benefits, including anti-inflammation, anti-allergy, and anti-cancer effects, although more research is needed in this area.

InChI:InChI=1/C10H8O4/c1-5-2-7(12)10-8(13)3-6(11)4-9(10)14-5/h2-4,11,13H,1H3

Upstream product

• 480-34-2 eugenin 
• 480-27-3 1-Methyl-3-(2',4',6'-trimethoxyphenyl)propan-1,3-dione 
• 1022-78-2 3-acetyl-5,7-dihydroxy-2-methyl-chromen-4-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-24-7 acetic anhydride 
• 108-73-6 3,5-dihydroxyphenol 
• 141-97-9 ethyl acetoacetate 
• 56147-47-8 2-methyl-4-oxo-4H-chromene-5,7-diyl diacetate 
• 1162-81-8 3-Acetyl-5,7-bis(acetyloxy)-2-methyl-4H-1-benzopyran-4-one 
• 128396-15-6 noreugenin 7-O-β-D-glucoside 
• 89701-85-9 6-β-C-glucopyranosyl-5,7-dihydroxy-2-methylchromone 
• 524-14-1 malonyl-CoA 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 144152-27-2 1-[2,4,6-tris(acetyloxy)phenyl]ethanone 

Downstream Products

• 31273-62-8 7-(1,1-dimethyl-prop-2-ynyloxy)-5-hydroxy-2-methyl-chromen-4-one 
• 4670-29-5 5-Hydroxy-2,8,8-trimethyl-8H-pyrano<2,3-h>chromone 
• 29507-75-3 spatheliachromen 
• 24672-78-4 pulverin 
• 578-72-3 5,7-dihydroxy-2-methyl-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one 
• 138459-41-3 7-(Benzyloxy)-6-bromo-5-methoxy-2-methyl-4H-1-benzopyran-4-one 
• 138459-40-2 7-(Benzyloxy)-8-bromo-5-methoxy-2-methyl-4H-1-benzopyran-4-one 
• 138459-44-6 5-(Acetyloxy)-7-(benzyloxy)-6-bromo-2-methyl-4H-1-benzopyran-4-one 
• 138459-45-7 7-(Benzyloxy)-5-hydroxy-8-<4-<3-(methoxycarbonyl)pyridyl>>-2-methyl-4H-1-benzopyran-4-one 
• 138459-43-5 7-(Benzyloxy)-5-methoxy-8-<4-<3-(methoxycarbonyl)pyridyl>>-2-methyl-4H-1-benzopyran-4-one 
• 138459-46-8 5-(Acetyloxy)-7-(benzyloxy)-6-<4-<3-(methoxycarbonyl)pyridyl>>-2-methyl-4H-1-benzopyran-4-one 
• 69735-24-6 schumanniophytine 
• 16639-46-6 7-allyloxy-5-hydroxy-2-methyl-4H-chromen-4-one 
• 17981-91-8 Ptaeroxylinol 

Relevant articles and documents

BIFLORIN, A CHROMONE-C-GLUCOSIDE FROM PANCRATIUM BIFLORUM

A new polyoxigenated chromone-C-glucoside, named biflorin, was isolated from the roots of Pancratium biflorum collected at flowering time.The structure of the compound was established as 5,7-dihydroxy-2-methylchromone-C6-β-D-glucopyranoside on the basis of comprehensive spectral analysis (UV, IR, 1H NMR, MS, D) and crucial chemical transformations of the compound and its derivatives.The biochemical significance of the occurence and ontogenic variations of biflorin and other polyoxygenated chromones in the title species is discussed.Key Word Index - Pancratium biflorum; Amaryllidaceae; roots; chromone-C-glucoside; biflorin; 5,7-dihydroxy-2-methylchromone-C6-β-D-glucopyranoside; chromone-metal ion complex; phosphodiesterase inhibitor.

Engineered biosynthesis of plant polyketides: Manipulation of chalcone synthase

Chalcone synthase (CHS) is a plant-specific type III polyketide synthase catalyzing condensation of 4-coumaroyl-CoA with three molecules of malonyl-CoA. Surprisingly, it was demonstrated that S338V mutant of Scutellaria baicalensis CHS produced octaketides SEK4/SEK4b from eight molecules of malonyl-CoA. Further, the octaketides-forming activity was dramatically increased in a CHS triple mutant (T197G/G256L/ S338T). The functional conversion is based on the simple steric modulation of a chemically inert residue lining the active-site cavity.

Engineered biosynthesis of plant polyketides: Chain length control in an octaketide-producing plant type III polyketide synthase

The chalcone synthase (CHS) superfamily of type III polyketide syntheses (PKSs) produces a variety of plant secondary metabolites with remarkable structural diversity and biological activities (e.g., chalcones, stilbenes, benzophenones, acrydones, phloroglucinols, resorcinols, pyrones, and chromones). Here we describe an octaketide-producing novel plant-specific type III PKS from aloe (Aloe arborescens) sharing 50-60% amino acid sequence identity with other plant CHS-superfamily enzymes. A recombinant enzyme expressed in Escherichia coli catalyzed seven successive decarboxylative condensations of malonyl-CoA to yield aromatic octaketides SEK4 and SEK4b, the longest polyketides known to be synthesized by the structurally simple type III PKS. Surprisingly, site-directed mutagenesis revealed that a single residue Gly207 (corresponding to the CHS's active site Thr197) determines the polyketide chain length and product specificity. Small-to-large substitutions (G207A, G207T, G207M, G207L, G207F, and G207W) resulted in loss of the octaketide-forming activity and concomitant formation of shorter chain length polyketides (from triketide to heptaketide) including a pentaketide chromone, 2,7-dihydroxy-5-methylchromone, and a hexaketide pyrone, 6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxy-2-pyrone, depending on the size of the side chain. Notably, the functional diversity of the type III PKS was shown to evolve from simple steric modulation of the chemically inert single residue lining the active-site cavity accompanied by conservation of the Cys-His-Asn catalytic triad. This provided novel strategies for the engineered biosynthesis of pharmaceutically important plant polyketides.

TMSI-Promoted vinylogous michael addition of siloxyfuran to 2-substituted chromones: A general approach for the total synthesis of chromanone lactone natural products

A concise and facile synthetic protocol for the construction of the 2-γ-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (±)-microdiplodiasone, (±)-lachnone C, and (±)-gonytolides C and G.

Structure-based engineering of a plant type III polyketide synthase: Formation of an unnatural nonaketide naphthopyrone

Pentaketide chromone synthase (PCS) from Aloe arborescens is a novel plant-specific type III polyketide synthase (PKS) that produces 5,7-dihydroxy-2-methylchromone from five molecules of malonyl-CoA. On the basis of the crystal structures of wild-type and M207G mutant PCS, the F80A/Y82A/M207G triple mutant was constructed and shown to produce an unnatural novel nonaketide naphthopyrone by sequential condensations of nine molecules of malonyl-CoA. This is the first demonstration of the formation of a nonaketide by the structurally simple type III PKS. A homology model predicted that the active-site cavity volume of the triple mutant is increased to 4 times that of the wild-type PCS.

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Synthesis and Antifungal Activity of Chromones and Benzoxepines from the Leaves of Ptaeroxylon obliquum

This study reports the first total synthesis of the bioactive oxepinochromones 12-O-acetyleranthin (8) (angular isomer) and 12-O-acetylptaeroxylinol (9) (linear isomer). The antifungal activity of these compounds and their derivatives was determined against Candida albicans and Cryptococcus neoformans. Most compounds had good selectivity between the two fungi and showed moderate to good activity. 12-O-Acetyleranthin (8) had the highest activity against C. albicans, with an MIC value of 9.9 μM, while 12-O-acetylptaeroxylinol (9), the compound present in Ptaeroxylon obliquum, had the highest activity against C. neoformans, with an MIC value of 4.9 μM.

Derivatives of Natural Product Agrimophol as Disruptors of Intrabacterial pH Homeostasis in Mycobacterium tuberculosis

This article reports the rational medicinal chemistry of a natural product, agrimophol (1), as a new disruptor of intrabacterial pH (pHIB) homeostasis in Mycobacterium tuberculosis (Mtb). Through the systematic investigation of the structure-activity relationship of 1, scaffold-hopping of the diphenylmethane scaffold, pharmacophore displacement strategies, and studies of the structure-metabolism relationship, a new derivative 5a was achieved. Compound 5a showed 100-fold increased potency in the ability to reduce pHIB to pH 6.0 and similarly improved mycobactericidal activity compared with 1 against both Mycobacterium bovis-BCG and Mtb. Compound 5a possessed improved metabolic stability in human liver microsomes and hepatocytes, lower cytotoxicity, higher selectivity index, and similar pKa value to natural 1. This study introduces a novel scaffold to an old drug, resulting in improved mycobactericidal activity through decreasing pHIB, and may contribute to the critical search for new agents to overcome drug resistance and persistence in the treatment of tuberculosis.