897-46-1

Basic information

• Product Name: 6,7-DIHYDROXY-4'-METHOXYISOFLAVONE
• Synonyms: TEXASIN;6,7-DIHYDROXY-4'-METHOXYISOFLAVONE;6,7-dihydroxy-3-(4-methoxyphenyl)-4-benzopyrone;3-(4-Methoxyphenyl)-6,7-dihydroxy-4H-1-benzopyran-4-one;6,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• CAS NO: 897-46-1
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• EINECS: 212-980-9
• Product Categories: Iso-Flavones
• Mol File: 897-46-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 546 °C at 760 mmHg
• Flash Point: 209.5 °C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 1.56E-12mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: 6,7-DIHYDROXY-4'-METHOXYISOFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-DIHYDROXY-4'-METHOXYISOFLAVONE(897-46-1)
• EPA Substance Registry System: 6,7-DIHYDROXY-4'-METHOXYISOFLAVONE(897-46-1)

Safety Data

• Hazardous Substances Data: 897-46-1(Hazardous Substances Data)

Usage

General Description

6,7-Dihydroxy-4'-methoxyisoflavone is a natural chemical compound that belongs to the isoflavone class of flavonoids. It is found in various plants, including legumes, and has been studied for its potential health benefits. 6,7-DIHYDROXY-4'-METHOXYISOFLAVONE has antioxidant properties, meaning it can help protect cells from damage caused by free radicals. Additionally, it has been shown to have anti-inflammatory effects, which may be beneficial for reducing the risk of certain chronic diseases. 6,7-Dihydroxy-4'-methoxyisoflavone has also been studied for its potential role in promoting bone health and reducing the risk of osteoporosis. Overall, this compound shows promise for various health benefits and continues to be the subject of research.

InChI:InChI=1/C16H12O5/c1-20-10-4-2-9(3-5-10)12-8-21-15-7-14(18)13(17)6-11(15)16(12)19/h2-8,17-18H,1H3

Upstream product

• 104-47-2 p-methoxybenzylnitrile 
• 533-73-3 1,2,4-Trihydroxybenzene 
• 76095-38-0 1-(2,4,5-trihydroxyphenyl)-2-(4'-methoxyphenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 290-87-9 1,3,5-Triazine 

Downstream Products

• 76397-85-8 C₁₆H₁₄O₅ 
• 76397-87-0 3,4-dihydro-6,7-dihydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran 
• 550-79-8 afromosin 
• 970-48-9 6-hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one 

Relevant articles and documents

Isolation of isoflavones from Iris kashmiriana Baker as potential anti proliferative agents targeting NF-kappaB

Cancer is possibly one of the most devastating and complex disease and therefore involves chemotherapy as one of the frontline strategies in its therapy. However, expected toxicity and resistance with chemotherapeutic agents encourage us to use the plant derived natural chemotherapeutic sources at the clinical stage of cancer therapy. In view of this strategy, herein new glycosides and isoflavonoids were isolated from Iris kashmiriana Baker and subjected to structure elucidation followed by their biological evaluation. Isolated compounds and their derivatives were purified by the column chromatography and structural identification was made by a combination of various spectroscopic technique vis. UV, IR, 1H NMR, 13C NMR, DEPT, 2-D NMR and mass spectrometry coupled with chemical analysis. Furthermore, an in silico library of isolated isoflavones and its analogues were designed. NF-kappaB (transcription factor that facilitates angiogenesis, inflammation, invasion and metastasis) was selected as a target to evaluate the anticancer and antioxidant activity of isoflavones and its analogues. Designed library of isoflavones and analogues were docked into the active site of NF-kappa B and the most active 15 analogues were selected for synthesis. Finally, all compounds were evaluated for their cytotoxicity against various cell lines and antioxidant activity with different methods that demonstrate their anti-cancer and anti-oxidant potential. The cell cycle specificity of the cytotoxicity was further analyzed by corresponding analysis, using flow cytometer. Most of the compounds exhibit moderate activity, whereas the 5,7,8-trihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one, 5,7,8-trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one, 5,7,8-triacetoxyoxy-3-(4-methoxyphenyl)-4H-chromen-4-one and 6,7-diacetoxyoxy-3-(4-methoxyphenyl)-4H-chromen-4-one showed distinct broad-spectrum anticancer activity with IC50 values ranges between 3.8 and 5.6?μg/mL. Cell cycle analysis indicates that these compounds induced cell cycle arrest at G2/M phase.

Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones

In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS.+ and DPPH. radicals with SC50 values of 11.3±0.3 and 9.4±0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9±4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.

Structure-activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2

Human lipoxygenase (hLO) isozymes have been implicated in a number of disease states and have attracted much attention with respect to their inhibition. One class of inhibitors, the flavonoids, have been shown to be potent lipoxygenase inhibitors but their study has been restricted to those compounds found in nature, which have limited structural variability. We have therefore carried out a comprehensive study to determine the structural requirements for flavonoid potency and selectivity against platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2. We conclude from this study that catechols are essential for high potency, that isoflavones and isoflavanones tend to select against 12-hLO, that isoflavans tend to select against 15-hLO-1, but few flavonoids target 15-hLO-2.