82517-12-2

Basic information

• Product Name: 5-Methyl-7-methoxyisoflavone
• Synonyms: METHYL-7-METHOXY-ISOFLAVONE, 5-;5-METHYL-7-METHOXYISOFLAVONE;7-METHOXY-5-METHYLISOFLAVONE;5-METHYL-7-METHOXYISOFLAVONE 99+%;5-Methyl-7-methoxyisoflavone 98.0%min;5-Methyl-7-methoxyisoflavone,98%;5-Methyl-7-methoxyis;7-Methoxy-5-Methyl-3-phenyl-4H-chroMen-4-one
• CAS NO: 82517-12-2
• Molecular Formula: C₁₇H₁₄O₃
• Molecular Weight: 266.29
• EINECS: 1308068-626-2
• Product Categories: Iso-Flavones;Heterocycles
• Mol File: 82517-12-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 116-120 °C
• Boiling Point: 349.5°C (rough estimate)
• Flash Point: 217.5 °C
• Appearance: white crystalline powder
• Density: 1.2327 (rough estimate)
• Vapor Pressure: 2.9E-08mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: 5-Methyl-7-methoxyisoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-7-methoxyisoflavone(82517-12-2)
• EPA Substance Registry System: 5-Methyl-7-methoxyisoflavone(82517-12-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 82517-12-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C17H14O3/c1-11-8-13(19-2)9-15-16(11)17(18)14(10-20-15)12-6-4-3-5-7-12/h3-10H,1-2H3

Synthetic route

1-(2-hydroxy-4-methoxy-6-methylphenyl)-2-phenylethan-1-one (860579-89-1) + orthoformic acid triethyl ester (122-51-0) → 5-methyl-7-methoxyisoflavone (82517-12-2)

Conditions	Yield
With piperidine; pyridine Yield given;

1,3-dimethoxy-5-methylbenzene (4179-19-5) → 5-methyl-7-methoxyisoflavone (82517-12-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3 2: piperidine, pyridine View Scheme

phenylacetyl chloride (103-80-0) → 5-methyl-7-methoxyisoflavone (82517-12-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3 2: piperidine, pyridine View Scheme

diethyl sulfate (64-67-5) + 7-hydroxy-5-methyl-3-phenyl-chromen-4-one (55338-30-2) + 5-methyl-7-ethoxy-isoflavone → 5-methyl-7-methoxyisoflavone (82517-12-2)

Conditions	Yield
With potassium carbonate In water

C11H9IO3 + phenylzinc(II) bromide (38111-44-3) → 5-methyl-7-methoxyisoflavone (82517-12-2)

Conditions	Yield
at 20℃; Negishi Coupling;

5-methyl-7-methoxyisoflavone (82517-12-2) → 3-(2-hydroxy-4-methoxy-6-methylphenyl)-4-phenyl-1H-pyrazole

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; Reflux;	95%

1H-benzimidazol-2-amine (934-32-7) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 2-(2-hydroxy-4-methoxy-5-methylphenyl)-3-phenyl-pyrimido[1,2-a]benzimidazole (1179998-26-5)

Conditions	Yield
With sodium methylate In methanol at 65℃; for 8h;	93%

5-methyl-7-methoxyisoflavone (82517-12-2) → 7-hydroxy-5-methyl-3-phenyl-chromen-4-one (55338-30-2)

Conditions	Yield
With aluminium trichloride In benzene	88%

5-methyl-7-methoxyisoflavone (82517-12-2) → 9-methoxy-11-methyl-2H-phenanthro[9,10-c]pyrazole (1428876-28-1)

Conditions	Yield
Stage #1: 5-methyl-7-methoxyisoflavone With hydrazine hydrate In ethanol at 80℃; Stage #2: In ethanol; water at 20℃; for 4h; Inert atmosphere; Irradiation;	86%

guanidine hydrochloride (50-01-1) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 2-amino-4-(2-hydroxy-4-methoxy-6-methylphenyl)-5-phenylpyrimidine (1338784-55-6)

Conditions	Yield
Stage #1: guanidine hydrochloride; 5-methyl-7-methoxyisoflavone With sodium hydroxide In ethanol for 4h; Reflux; Stage #2: With hydrogenchloride In ethanol; water	82%

Arg (7200-25-1) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 2-amino-5-[4-(2-hydroxy-4-methoxy-6-methylphenyl)-5-phenylpyrimidin-2-ylamino]pentanoic acid

Conditions	Yield
With sodium hydroxide In methanol for 5h; Reflux;	81%

3-aminopyrazole (1820-80-0) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 6-phenyl-7-(2-hydroxy-4-methoxy-6-methylphenyl)pyrazolo[1,5-a]pyrimidine (1307770-03-1)

Conditions	Yield
With sodium methylate In methanol at 70℃; for 13h;	79%

5-Aminoimidazole-4-carboxamide (360-97-4) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 8-carbamoyl-4-(2-hydroxy-4-methoxy-6-methylphenyl)-3-phenylimidazo[1,5-a]pyrimidine (1380484-08-1)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 0.166667h; Microwave irradiation;	79%

5-methyl-7-methoxyisoflavone (82517-12-2) + cyanoacetic acid amide (107-91-5) → 3-cyano-6-(4-methoxy-6-methyl-2-hydroxyphenyl)-5-phenylpyridin-2(1H)-one (1456626-63-3)

Conditions	Yield
With sodium hydroxide In ethanol for 1.5h; Reflux;	78%

5-methyl-7-methoxyisoflavone (82517-12-2) + 5-amino-2H-pyrazol-3-ol (53666-79-8) → C20H17N3O3 (1233690-15-7, 1351362-71-4)

Conditions	Yield
With sodium methylate In methanol for 16h; Reflux; chemoselective reaction;	77%

2-cyanothioacetamide + 5-methyl-7-methoxyisoflavone (82517-12-2) → 3-cyano-6-(4-methoxy-6-methyl-2-hydroxyphenyl)-5-phenylpyridine-2(1H)-thione (1427272-62-5)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 90℃; for 5h;	76%

3-methyl-5-aminopyrazole (31230-17-8) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 2-methyl-6-phenyl-7-(2-hydroxyl-4-methoxy-6-methylphenyl)pyrazolo[1,5-a]pyrimidine (1606136-74-6)

Conditions	Yield
With sodium methylate In ethanol for 24h; Reflux; chemoselective reaction;	75%

amidinothiocarbamide (2114-02-5) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 1-[4-(2-hydroxy-4-methoxy-6-methylphenyl)-5-phenylpyrimidin-2-yl]thiourea (1233943-89-9)

Conditions	Yield
With sodium methylate In methanol for 3.5h; Reflux;	65%

2-aminoimidazole hemisulfate (1450-93-7, 36946-29-9, 42383-61-9) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 5-(2-hydroxy-4-methoxy-6-methylphenyl)-6-phenylimidazo[1,2-a]pyrimidine (1357294-47-3)

Conditions	Yield
Stage #1: 2-aminoimidazole hemisulfate; 5-methyl-7-methoxyisoflavone With sodium hydroxide In water; dimethyl sulfoxide at 100℃; for 0.5h; Microwave irradiation; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide	65%

3-Amino-4-cyanopyrazole (16617-46-2) + 5-methyl-7-methoxyisoflavone (82517-12-2) → 3-cyano-6-phenyl-7-(2-hydroxyl-4-methoxy-6-methylphenyl)pyrazolo[1,5-a]pyrimidine (1365659-26-2)

Conditions	Yield
With sodium methylate In methanol at 70℃; for 16h;	59%

5-methyl-7-methoxyisoflavone (82517-12-2) + 4H-1,2,4-triazol-3-amine (61-82-5) → 6-phenyl-7-(2-hydroxy-4-methoxy-6-methylphenyl)-[1,2,4]triazolo[4,3-a]pyrimidine (1232561-85-1)

Conditions	Yield
With sodium methylate In dimethyl sulfoxide at 100℃; for 0.2h; Microwave irradiation;	54%

5-methyl-7-methoxyisoflavone (82517-12-2) + 3-amino-5-hydroxy-1,2,4-triazole (1003-35-6) → 3-hydroxy-6-phenyl-7-(2-hydroxy-4-methoxy-6-methylphenyl)-[1,2,4]triazolo[4,3-a]pyrimidine (1232562-06-9)

Conditions	Yield
With sodium methylate In dimethyl sulfoxide at 100℃; for 0.25h; Microwave irradiation;	50%

5-methyl-7-methoxyisoflavone (82517-12-2) → [(5-Methyl-4-oxo-3-phenyl-4H-1-benzopyran-7-yl)oxy]acetic acid (112953-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / AlCl3 / benzene 2: 78.5 percent / K2CO3 3: 76.2 percent / NaOH View Scheme

5-methyl-7-methoxyisoflavone (82517-12-2) → (5-Methyl-4-oxo-3-phenyl-4H-chromen-7-yloxy)-acetic acid ethyl ester (112953-75-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / AlCl3 / benzene 2: 78.5 percent / K2CO3 View Scheme

5-methyl-7-methoxyisoflavone (82517-12-2) → 4-methoxy-6-methyl-7a-phenyl-1a,7a-dihydrobenzopyrano[2,3-b]azirin-7-one

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; hydroxylamine hydrochloride / ethanol / Reflux 2: ethanol; water / 1 h / 20 °C / Inert atmosphere; Irradiation View Scheme

5-methyl-7-methoxyisoflavone (82517-12-2) → C17H15NO3

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In ethanol Reflux;

5-methyl-7-methoxyisoflavone (82517-12-2) → 1-(2-hydroxy-4-methoxy-6-methylphenyl)-2-phenylethan-1-one (860579-89-1)

Conditions	Yield
With sodium hydroxide In methanol; water at 60℃;

5-methyl-7-methoxyisoflavone (82517-12-2) → 7-hydroxy-3-methoxy-1-methyl-6H-naphtho[2,3-c]chromen-6-one

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; methanol / 60 °C 2: toluene-4-sulfonic acid / toluene; para-xylene / 150 °C View Scheme

Upstream product

• 860579-89-1 1-(2-hydroxy-4-methoxy-6-methylphenyl)-2-phenylethan-1-one 
• 122-51-0 orthoformic acid triethyl ester 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 103-80-0 phenylacetyl chloride 
• 64-67-5 diethyl sulfate 
• 55338-30-2 7-hydroxy-5-methyl-3-phenyl-chromen-4-one 
• 38111-44-3 phenylzinc(II) bromide 

Downstream Products

• 55338-30-2 7-hydroxy-5-methyl-3-phenyl-chromen-4-one 
• 112953-45-4 [(5-Methyl-4-oxo-3-phenyl-4H-1-benzopyran-7-yl)oxy]acetic acid 
• 112953-75-0 (5-Methyl-4-oxo-3-phenyl-4H-chromen-7-yloxy)-acetic acid ethyl ester 
• 1179998-26-5 2-(2-hydroxy-4-methoxy-5-methylphenyl)-3-phenyl-pyrimido[1,2-a]benzimidazole 
• 1233690-15-7 C₂₀H₁₇N₃O₃ 
• 1232561-85-1 6-phenyl-7-(2-hydroxy-4-methoxy-6-methylphenyl)-[1,2,4]triazolo[4,3-a]pyrimidine 
• 1232562-06-9 3-hydroxy-6-phenyl-7-(2-hydroxy-4-methoxy-6-methylphenyl)-[1,2,4]triazolo[4,3-a]pyrimidine 
• 1233943-89-9 1-[4-(2-hydroxy-4-methoxy-6-methylphenyl)-5-phenylpyrimidin-2-yl]thiourea 
• 1307770-03-1 6-phenyl-7-(2-hydroxy-4-methoxy-6-methylphenyl)pyrazolo[1,5-a]pyrimidine 
• 1357294-47-3 5-(2-hydroxy-4-methoxy-6-methylphenyl)-6-phenylimidazo[1,2-a]pyrimidine 
• 1338784-55-6 2-amino-4-(2-hydroxy-4-methoxy-6-methylphenyl)-5-phenylpyrimidine 
• 1365659-26-2 3-cyano-6-phenyl-7-(2-hydroxyl-4-methoxy-6-methylphenyl)pyrazolo[1,5-a]pyrimidine 
• 1380484-08-1 8-carbamoyl-4-(2-hydroxy-4-methoxy-6-methylphenyl)-3-phenylimidazo[1,5-a]pyrimidine 
• 1427272-62-5 3-cyano-6-(4-methoxy-6-methyl-2-hydroxyphenyl)-5-phenylpyridine-2(1H)-thione 

Relevant articles and documents

Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1H-Pyrazoles derivatives

A series of 3,4-diaryl-1H-pyrazoles derivatives were designed and synthesized by the reaction of 3-heteroarylchromones and 3-phenylchromones with hydrazine hydrate in good yields. All of those compounds were characterized by 1H NMR, 13C NMR, IR, and HRMS. Moreover, 3-(2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-1H-pyrazole and 3-(2,4-dihydroxy phenyl)-4-(4-methoxyphenyl)-1H-pyrazole were further conformed by the single crystal X-ray diffraction. In addition, the antifungal activity against five phytopathogenic fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani and Fusarium solani) of 3,4-diaryl-1H-pyrazoles were evaluated. 3-(2-Hydroxy-4-isopropoxyphenyl)-4-phenyl-1H-pyrazole was more better and broader inhibitory effect on Cytospora sp., C. gloeosporioides, A. solani and Fusarium solani with IC50 values of 26.96, 28.84, 16.77 and 22.10 μg/mL, respectively. 4-(4-Fluorophenyl)-3-(2-hydroxy-4-methoxyphenyl)-1H-pyrazole exhibited fairly effective antifungal activity against Cytospora sp., C. gloeosporioides and A. solani with IC50 values of 11.91, 14.92 and 16.98 μg/mL, respectively.

Metabolic 5-methyl-isoflavone-derivatives, process for the preparation thereof and compositions containing the same

Nonestrogenic 5-methyl-alkoxy-isoflavone, namely, 5-methyl-7-methoxy-isoflavone, 5-methyl-7-ethoxy-isoflavone, 5-methyl-7-isopropoxy-isoflavone, and 5-methyl-7-(2-hydroxy-ethoxy)-isoflavone are useful as weight-gain promoters in feeds from which the 7-methoxy and 7-ethoxy isoflavones have been excluded because of estrogenic effects. They are more effective than 7-isopropoxy-isoflavone as well.