491-80-5

Basic information

• Product Name: 5,7-Dihydrox -4'-methoxyisoflavone
• Synonyms: 5,7-dihydroxy-3-(4-methoxyphenyl)-4h-1-benzopyran-4-on;5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-Benzopyran-4-one;APIGENIN 4-METHYL ETHER;BIOCHANIN A;5,7-DIHYDROXY-4'-METHOXYISOFLAVONE;5,7-DIHYDROXY-4-METHOXYISOFLAVONE;Genistein 4′-methyl ether ;5,7-dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one
• CAS NO: 491-80-5
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• EINECS: 207-744-7
• Product Categories: Iso-Flavones;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 491-80-5.mol

Chemical Properties

• Melting Point: 210-213 °C(lit.)
• Boiling Point: 518.6 °C at 760 mmHg
• Flash Point: 198.2 °C
• Appearance: /Powder
• Density: 1.42 g/cm³
• Vapor Pressure: 2.25E-11mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: 0-6°C
• Solubility: acetone: 10 mg/mL, clear, brown
• PKA: 6.50±0.20(Predicted)
• Water Solubility: Soluble in water (<1 mg/ml at 25°C), chloroform, methanol, DMSO (57 mg/ml at 25°C), and ethanol (9 mg/ml at 25°C).
• BRN: 278107
• CAS DataBase Reference: 5,7-Dihydrox -4'-methoxyisoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-Dihydrox -4'-methoxyisoflavone(491-80-5)
• EPA Substance Registry System: 5,7-Dihydrox -4'-methoxyisoflavone(491-80-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DJ3002500
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 491-80-5(Hazardous Substances Data)

Usage

Uses

Used in Dietary Cancer Prophylaxis:
5,7-Dihydrox -4'-methoxyisoflavone is used as a chemopreventive agent for its putative benefits in dietary cancer prophylaxis. It inhibits metabolic activation of benzo[a]pyrene and has been found to induce sulfotransferases for xenobiotic detoxification, which has been proposed as a mechanism of its cancer preventive effects.
Used in Antineoplastic Applications:
5,7-Dihydrox -4'-methoxyisoflavone is used as an antineoplastic agent, acting as an inhibitor of cancer cell proliferation, differentiation, and chemoprevention. It is a selective agonist at ER-β estrogen receptors, which may have chemopreventive efficacy against breast cancer, while its low activity at ER-α estrogen receptors makes it essentially devoid of uterotrophic activity.
Used in Treatment of Diabetes Type 2:
5,7-Dihydrox -4'-methoxyisoflavone is used as a pharmacological agent for the treatment of diabetes type 2, as it acts as an agonist of PPARgamma, a nuclear receptor that is a current target for diabetes treatment.
Used in Cardiovascular Applications:
5,7-Dihydrox -4'-methoxyisoflavone is used as a cardiovascular agent, as it reduces arterial resistance and enhances microcirculation, potentially through effects on potassium and/or calcium ion channels.
Used in Apoptosis Induction and Nitric Oxide Synthase Inhibition:
5,7-Dihydrox -4'-methoxyisoflavone is used as an apoptosis inducer and nitric oxide synthase inhibitor, contributing to its potential therapeutic applications in various diseases and conditions.

Biochem/physiol Actions

Biochanin A is an isoflavone phytoestrogen found in red clover (Trifolium pratense) that is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects.

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

Upstream product

• 113029-08-6 2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone 
• 15485-66-2 2,4,6-trihydroxy-4'-methoxydeoxybenzoin 
• 109-94-4 formic acid ethyl ester 
• 104-01-8 4-Methoxyphenylacetic acid 
• 108-73-6 3,5-dihydroxyphenol 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 485-80-3 S-adenosyl-L-methionine 
• 1236208-90-4 3-iodo-5,7-bis(methoxymethoxy)-4H-1-benzopyran-4-one 
• 1236208-89-1 3-(N,N-dimethylamino)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 1005418-09-6 5-hydroxy-7-(methoxymethoxy)-3-(4-methoxyphenyl)-4H-chromen-4-one 

Downstream Products

• 15485-66-2 2,4,6-trihydroxy-4'-methoxydeoxybenzoin 
• 1162-82-9 4',5,7-trimethoxyisoflavone 
• 670225-99-7 6,8-dichlorobiochanin A 
• 1173791-14-4 5-hydroxy-3-(4-methoxyphenyl)-7-(2-nitrophenylacetoxy)-chromen-4-one 
• 1173791-10-0 5-hydroxy-3-(4-methoxyphenyl)-7-(3-nitrophenylacetoxy)-chromen-4-one 
• 1173791-16-6 5-hydroxy-3-(4-methoxyphenyl)-7-[2-(2-nitrophenyl)-2,2-dimethylacetoxy]chromen-4-one 
• 116535-00-3 7-benzyloxy-5-hydroxy-3-(4-methoxyphenyl)chromen-4-one 
• 1173791-07-5 5-hydroxy-3-(4-methoxyphenyl)-7-(4-nitrobenzyloxy)-chromen-4-one 
• 1173791-19-9 5-hydroxy-3-(4-methoxyphenyl)-7-[3-methyl-3-(3,6-dimethyl-1,4-benzoquinon-2-yl)butan-1-oyloxy]chromen-4-one 
• 81267-69-8 5,7-dihydroxy-4'-methoxyisoflavane 

Relevant articles and documents

Isoflavonoid glycosides from Dalbergia sissoo

Two isoflavone glycosides, biochanin A 7-O-[β-D-apiofuranosyl-(1 → 5)-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside] and tectorigenin 7-O-[β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside], were isolated from Dalbergia sissoo. Their structures were elucidate

Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation

In this study, polyhydroxyisoflavones that directly prevent the aggregation of both amyloid β (Aβ) and tau were expediently synthesized via divergent Pd(0)-catalyzed Suzuki-Miyaura coupling and then biologically evaluated. By preliminary structure–activity relationship studies using thioflavin T (ThT) assays, an ortho-catechol containing isoflavone scaffold was proven to be crucial for preventing both Aβ aggregation and tau-mediated neurofibrillary tangle formation. Additional TEM experiment confirmed that ortho-catechol containing isoflavone 4d significantly prevented the aggregation of both Aβ and tau. To investigate the mode of action (MOA) of 4d, which possesses an ortho-catechol moiety, 1H-15N HSQC NMR analysis was thoroughly performed and the result indicated that 4d could directly inhibit both the formation of Aβ42 fibrils and the formation of tau-derived neurofibrils, probably through the catechol-mediated nucleation of tau. Finally, 4d was demonstrated to alleviate cognitive impairment and pathologies related to Alzheimer's disease in a 5XFAD transgenic mouse model.

Synthesis method of biochanin A

The invention discloses a synthesis method of biochanin A. The synthesis method comprises the following steps: (1) carrying out condensation reaction on p-methoxyacetophenone and N-bromosuccinimide in the presence of absolute ethyl alcohol to obtain Alpha-bromo-4-methoxyacetophenone; and (2) by taking absolute ethyl alcohol as a reaction solvent, carrying out condensation reaction on 2, 4, 6-trihydroxy benzaldehyde and Alpha-bromo-4-methoxyacetophenone in the presence of a catalyst, evaporating reaction liquid, and separating and purifying a solid product by using column chromatography to obtain the biochanin A. The novel catalyst is adopted for catalysis, the product yield is high, reaction conditions are mild, and raw materials of the catalyst are easy to obtain and low in price. The synthesis method disclosed by the invention is simple in process, low in cost, time-saving, high in yield, low in equipment corrosion degree and suitable for industrial production.

Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids

Methylation of free hydroxyl groups is an important modification for flavonoids. It not only greatly increases absorption and oral bioavailability of flavonoids, but also brings new biological activities. Flavonoid methylation is usually achieved by a specific group of plant O-methyltransferases (OMTs) which typically exhibit high substrate specificity. Here we investigated the effect of several residues in the binding pocket of the Clarkia breweri isoeugenol OMT on the substrate scope and regioselectivity against flavonoids. The mutation T133M, identified as reported in our previous publication, increased the activity of the enzyme against several flavonoids, namely eriodictyol, naringenin, luteolin, quercetin and even the isoflavonoid genistein, while a reduced set of amino acids at positions 322 and 326 affected both, the activity and the regioselectivity of the methyltranferase. On the basis of this work, methylated flavonoids that are rare in nature were produced in high purity.

Cytosine N-isoflavone compound as well as preparation method and application thereof

The invention relates to a cytosine N-isoflavone compound as well as a preparation method and application thereof. The compound has a structural formula as shown in the specification, wherein R1 is selected from one of hydroxyl, alkoxy, amido or halo, R2 is selected from one of hydrogen, alkyl or aryl, and R3 is selected from one or a combination of several of hydroxyl, alkoxy, amido or halo. Compared with the prior art, the cytosine N-isoflavone compound has the characteristic that an isoflavone compound serving as a structural unit is spliced to N on the 12th position of cytosine by using acombined synthesis technology, so that a series of cytosine-isoflavone derivatives are synthesized, and a novel active pharmacological action is exerted.

Synthesis, Characterization, and Antioxidant Activities of Genistein, Biochanin A, and Their Analogues

A series of naturally occurring genistein (3) and biochanin A (4) compounds and their analogues were synthesized from phloroglucinol. The structures of all the synthesized compounds were established by the combined use of 1HNMR, 13CNMR, IR spectral data, and mass spectrometry; their antioxidant activities were investigated. Most of the synthesized compounds show moderate-to-high activity; only two compounds exhibit no significant activity.

Synthesis method of biochanin A

The invention provides a synthesis method of biochanin A. The synthesis method includes: under room temperature, adding phosphorus oxychloride into phloroglucinol, 4-Methoxybenzyl cyanide and isopropyl ether, performing hydrolysis after reaction is completed, and decoloring with activated carbon to obtain an intermediate; allowing the obtained intermediate and methylsufonyl chloride to generate crude products of the biochanin A in DMF (dimethyl formamide) in a ring-closing manner; performing recrystallization on the obtained crude products of the biochanin A by adopting ethyl alcohol and decoloring with the activated carbon to obtain the biochanin A. The synthesis method is simple in process, low in cost, timesaving, high in yield, low in equipment corrosiveness and suitable for industrialized production.

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.

Chevalierinoside B and C: Two new isoflavonoid glycosides from the stem bark of Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri Beille)

Chevalierinosides B (1) and C (2), two new isoflavonoid glycosides, characterized as biochanin A 7-O-[β-d-apiofuranosyl-(1→2)-β-d- glucopyranoside] and genistein 7-O-[β-d-apiofuranosyl-(1→2)-β-d- glucopyranoside], together with the known isoflavonoids, chevalierinoside A (3) and genistein 7-O-β-d-glucopyranoside (4), kaempferol 3-O-β-d- glucopyranoside (5) and triterpenes, friedelin (6), betulinic acid (7), 30-oxobetulinic acid (8), 30-hydroxybetulinic acid (9), were isolated from the stem bark of Antidesma laciniatum Muell. Arg. (syn. Antidesma chevalieri Beille). Their structures were established by direct interpretation of their spectral data, mainly HR-TOFESIMS, 1D-NMR (1H, 13C and DEPT) and 2D-NMR (COSY, NOESY, TOCSY, HSQC and HMBC), and by comparison with the literature.

Synthesis and aminomethylation of 7-hydroxy-5-methoxyisoflavones

A synthetic method for 7-hydroxy-5-methoxyisoflavones starting from 5,7-dihydroxyisoflavones was developed. Dimethylcarbamoylchloride was proposed for protection of the 7-hydroxy group. Aminomethylation of the synthesized 7-hydroxy-5-methoxyisoflavones by formaldehyde aminals was studied.