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

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

Uses

Used in Pharmaceutical Industry:
2-Methyl-5,7-dihydroxychromone is used as a potential therapeutic agent for its antioxidant properties, which can help protect cells from oxidative stress and damage. Its potential health benefits, such as anti-inflammation, anti-allergy, and anti-cancer effects, make it a promising candidate for further research and development in the pharmaceutical field.
Used in Cosmetic Industry:
In the cosmetic industry, 2-Methyl-5,7-dihydroxychromone is used as a natural pigment for coloration in various products, such as creams, lotions, and makeup. Its antioxidant properties may also contribute to the formulation of anti-aging and skin protection products, providing additional benefits to consumers.
Used in Food Industry:
2-Methyl-5,7-dihydroxychromone is used as a natural food colorant, providing a yellow hue to various food products. Its antioxidant properties may also help in preserving the freshness and quality of the food, extending its shelf life and enhancing its nutritional value.
Used in Agricultural Industry:
In agriculture, 2-Methyl-5,7-dihydroxychromone can be used as a natural pesticide or growth promoter, thanks to its antioxidant and potential health benefits. It may help protect plants from oxidative stress and improve their overall health, leading to increased crop yields and better quality produce.

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

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 128396-15-6 noreugenin 7-O-β-D-glucoside 
• 127-09-3 sodium acetate 
• 144152-27-2 1-[2,4,6-tris(acetyloxy)phenyl]ethanone 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 524-14-1 malonyl-CoA 
• 89701-85-9 6-β-C-glucopyranosyl-5,7-dihydroxy-2-methylchromone 
• 1162-81-8 3-Acetyl-5,7-bis(acetyloxy)-2-methyl-4H-1-benzopyran-4-one 
• 56147-47-8 2-methyl-4-oxo-4H-chromene-5,7-diyl diacetate 
• 141-97-9 ethyl acetoacetate 
• 108-24-7 acetic anhydride 
• 1022-78-2 3-acetyl-5,7-dihydroxy-2-methyl-chromen-4-one 
• 480-27-3 1-Methyl-3-(2',4',6'-trimethoxyphenyl)propan-1,3-dione 

Downstream Products

• 16639-46-6 7-allyloxy-5-hydroxy-2-methyl-4H-chromen-4-one 
• 33845-34-0 10-(3,3-dimethylallyl)spatheliachromene 
• 34411-93-3 spatheliabischromene 
• 27305-38-0 alloptaeroxylin acetate 
• 29507-75-3 spatheliachromen 
• 4670-29-5 5-Hydroxy-2,8,8-trimethyl-8H-pyrano<2,3-h>chromone 
• 69735-24-6 schumanniophytine 
• 138459-46-8 5-(Acetyloxy)-7-(benzyloxy)-6-<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 
• 138459-45-7 7-(Benzyloxy)-5-hydroxy-8-<4-<3-(methoxycarbonyl)pyridyl>>-2-methyl-4H-1-benzopyran-4-one 
• 138459-44-6 5-(Acetyloxy)-7-(benzyloxy)-6-bromo-2-methyl-4H-1-benzopyran-4-one 
• 138459-40-2 7-(Benzyloxy)-8-bromo-5-methoxy-2-methyl-4H-1-benzopyran-4-one 
• 138459-41-3 7-(Benzyloxy)-6-bromo-5-methoxy-2-methyl-4H-1-benzopyran-4-one 
• 138459-38-8 7-(Benzyloxy)-8-bromo-5-hydroxy-2-methyl-4H-1-benzopyran-4-one 

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.

A plant type III polyketide synthase that produces pentaketide chromone

A novel plant-specific type III polyketide synthase (PKS) that catalyzes formation of a pentaketide chromone, 5,7-dihydroxy-2-methylchromone, from five molecules of malonyl-CoA, was cloned and sequenced from aloe (Aloe arborescens). Site-directed mutagenesis revealed that Met207 (corresponding to Thr197 in CHS) determines the polyketide chain length and the product specificity of the enzyme; remarkably, replacement of a single amino acid residue, Met207, with Gly yielded a mutant enzyme that efficiently produces aromatic octaketides, SEK4 and SEK4b, the products of the minimal PKS for actinorhodin (act from Streptomyces coelicolor), from eight molecules of malonyl-CoA. This provided new insights into the catalytic functions and specificities of the CHS-superfamily type III PKS enzymes. Copyright

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.

Anti-inflammatory chromone alkaloids and glycoside from Dysoxylum binectariferum

Herein we report isolation of a new chromone alkaloid chrotacumine K (12) from fruits and a chromone glycoside schumaniofioside A (13) from leaves of Dysoxylum binectariferum Hook f. Schumaniofioside A is reported for the first time from Meliaceae family. Other known alkaloids isolated include rohitukine (1) and chrotacumine E (6). The structure of new alkaloid 12 was elucidated on the basis of extensive 1D and 2D NMR analysis, synthesis and chemical hydrolysis. Chemically, chrotacumine K (12) is a 3′-O-acetyl rohitukine which on chemical or enzymatic hydrolysis produces rohitukine. The new alkaloid 12 is also present in seeds and stem-barks of this plant. The glycoside schumaniofioside A (13) is present only in leaves, and in abundance (～1% w/w of dried leaves). The isolated compounds and extracts were evaluated for in vitro effect on the proinflammatory cytokines (TNF-α and IL-6) in human monocytic THP-1 cells. The alkaloid 12 displayed potent inhibition (57%) of TNF-α at 0.3 μM, and was non-toxic to THP-1 cells up to 40 μM, indicating its excellent therapeutic window. Furthermore, a nitrobenzoyl ester analog 15e showed better inhibition of IL-6 than parent natural product chrotacumine K.

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.

CHROMONE GLYCOSIDES DROM SCHUMANNIOPHYTON MAGNIFICUM

Two new chromone glycosides, schumanniofiosides A and B have been isolated from the root bark of Schumanniophython magnificum and their structures shown to be 2-methyl-5,7-dihydroxychromone 5-O-β-D-glucopyranoside and 2-methyl-5,7-dihydroxychromone 7-O-β-D-glocopyranosyl-(1 2)-apiofuranoside, respectively.The structures were elucidated by a combination of spectral data and chemical degradation.

Flavonoid-based inhibitors of the Phi-class glutathione transferase from black-grass to combat multiple herbicide resistance

The evolution and growth of multiple-herbicide resistance (MHR) in grass weeds continues to threaten global cereal production. While various processes can contribute to resistance, earlier work has identified the phi class glutathione-S-transferase (AmGSTF1) as a functional biomarker of MHR in black-grass (Alopecurus myosuroides). This study provides further insights into the role of AmGSTF1 in MHR using a combination of chemical and structural biology. Crystal structures of wild-type AmGSTF1, together with two specifically designed variants that allowed the co-crystal structure determination with glutathione and a glutathione adduct of the AmGSTF1 inhibitor 4-chloro-7-nitro-benzofurazan (NBD-Cl) were obtained. These studies demonstrated that the inhibitory activity of NBD-Cl was associated with the occlusion of the active site and the impediment of substrate binding. A search for other selective inhibitors of AmGSTF1, using ligand-fishing experiments, identified a number of flavonoids as potential ligands. Subsequent experiments using black-grass extracts discovered a specific flavonoid as a natural ligand of the recombinant enzyme. A series of related synthetic flavonoids was prepared and their binding to AmGSTF1 was investigated showing a high affinity for derivatives bearing a O-5-decyl-α-carboxylate. Molecular modelling based on high-resolution crystal structures allowed a binding pose to be defined which explained flavonoid binding specificity. Crucially, high binding affinity was linked to a reversal of the herbicide resistance phenotype in MHR black-grass. Collectively, these results present a nature-inspired new lead for the development of herbicide synergists to counteract MHR in weeds. This journal is

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.