480-23-9

Basic information

• Product Name: 3',4',5,7-TETRAHYDROXYISOFLAVONE
• Synonyms: OROBOL;3’,4’,5,7-tetrahydroxy-isoflavon;5,7,3’,4’-tetrahydroxyisoflavone;5,7-dihydroxy-3-(3,4-dihydroxyphenyl)-4h-1-benzopyran-4-on;5,7-dihydroxy-3-(3,4-dihydroxyphenyl)-4h-1-benzopyran-4-one;isoluteolin;3',4',5,7-TETRAHYDROXYISOFLAVONE;3',4',5,7-Tetrahydroxyisoflavone Orobol
• CAS NO: 480-23-9
• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.24
• Product Categories: Iso-Flavones
• Mol File: 480-23-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 270 °C
• Boiling Point: 616.1 °C at 760 mmHg
• Flash Point: 239.5 °C
• Appearance: /
• Density: 1.654 g/cm³
• PKA: 6.37±0.20(Predicted)
• CAS DataBase Reference: 3',4',5,7-TETRAHYDROXYISOFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',4',5,7-TETRAHYDROXYISOFLAVONE(480-23-9)
• EPA Substance Registry System: 3',4',5,7-TETRAHYDROXYISOFLAVONE(480-23-9)

Safety Data

• Hazardous Substances Data: 480-23-9(Hazardous Substances Data)

Usage

General Description

3',4',5,7-Tetrahydroxyisoflavone is a chemical compound classified under the isoflavone group, which is a type of flavonoid. As implied by the name, it has four hydroxyl functional groups attached to it. 3',4',5,7-TETRAHYDROXYISOFLAVONE is naturally present in several plants and known for its antioxidant activity. It is commonly found in dietary sources such as soy and other legumes. As an isoflavone, it may exhibit both estrogenic and anti-estrogenic activity, and therefore, it has been explored for its potential benefits for cardiovascular health, bone health, and also for alleviating symptoms of menopause. However, more research is needed to fully understand its health effects.

Synthetic route

3-(3,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one (53084-11-0) → orobol (480-23-9)

Conditions	Yield
With pyridine hydrochloride at 150℃; Inert atmosphere;	70%

3-(3',4'-dihydroxyphenyl)-5,7-dimethoxy-4H-chromen-4-one → orobol (480-23-9)

Conditions	Yield
With boron tribromide In dichloromethane at 60℃; for 18h;	10%

3-(3,4-dimethoxyphenyl)-5,7-dimethoxychromen-4-one (40316-84-5) → orobol (480-23-9)

Conditions	Yield
With hydrogen iodide; acetic anhydride at 150℃;

8-(β-D-glucopyranosyl)orobol (66026-81-1) → orobol (480-23-9)

Conditions	Yield
With hydrogen iodide; phenol Heating;	20 mg

6,8-di-C-β-D-glucopyranosyl-3',4',5,7-tetrahydroxyisoflavone (118949-94-3) → orobol (480-23-9)

Conditions	Yield
With hydrogen iodide; phenol Heating;	25 mg

Acetic acid 2-[2-(3,4-dihydroxy-phenyl)-3,3-dimethoxy-propionyl]-3,5-dihydroxy-phenyl ester → orobol (480-23-9)

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating; Yield given;

3',4',5,7-tetrahydroxyisoflavone β-D-glucopyranoside (20486-33-3) → orobol (480-23-9)

Conditions	Yield
With trifluoroacetic acid for 2h; Heating;

oroboside → orobol (480-23-9)

Conditions	Yield
With emulsin
With sulfuric acid

santal → orobol (480-23-9)

Conditions	Yield
With hydrogen iodide

2,2'-azobis-(2,4-dimethylvaleronitrile) (4419-11-8) + 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → orobol (480-23-9) + 2-[1-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-4-oxo-cyclohexa-2,5-dienylperoxy]-2,4-dimethyl-pentanenitrile + 2-[1-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-4-oxo-cyclohexa-2,5-dienyloxy]-4-hydroperoxy-2,4-dimethyl-pentanenitrile + 2-[1-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-4-oxo-cyclohexa-2,5-dienylperoxy]-4-hydroperoxy-2,4-dimethyl-pentanenitrile

Conditions	Yield
In acetonitrile at 50℃; for 3h; Product distribution; Further Variations:; various reaction time;

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → orobol (480-23-9)

Conditions	Yield
With NADPH; cytochrome P450 In water at 37℃; pH=7.4; Enzyme kinetics; Further Variations:; Reagents;
With ascorbic acid In dimethyl sulfoxide at 50℃; for 1.5h; pH=9; Enzymatic reaction;

7,3',4'-trihydroxy-5-O-β-D-(2''-O-acetyl)xylopyranosyl-isoflavone → orobol (480-23-9)

Conditions	Yield
With hydrogenchloride for 2h; Heating;	3 mg

Acetic acid 3,5-bis-benzyloxy-2-[(E)-3-(3,4-bis-benzyloxy-phenyl)-acryloyl]-phenyl ester → orobol (480-23-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: thallium nitrate / CHCl3 / Ambient temperature 2: H2, triethylamine / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature 3: 5percent HCl / methanol / 2 h / Heating View Scheme

Acetic acid 3,5-bis-benzyloxy-2-[2-(3,4-bis-benzyloxy-phenyl)-3,3-dimethoxy-propionyl]-phenyl ester → orobol (480-23-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2, triethylamine / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature 2: 5percent HCl / methanol / 2 h / Heating View Scheme

eriodictyol (552-58-9) → orobol (480-23-9)

Conditions	Yield
With NADPH disodium salt; D-Galactose In dimethyl sulfoxide at 30℃; for 72h; Microbiological reaction;

3,5-dimethoxyphenol (500-99-2) → orobol (480-23-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: boron trifluoride diethyl etherate / 4 h / 75 °C 2: boron trifluoride diethyl etherate; methanesulfonyl chloride / 2 h / 100 °C 3: boron tribromide / dichloromethane / 18 h / 60 °C View Scheme

3,4-dihydroxyphenylacetate (102-32-9) → orobol (480-23-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: boron trifluoride diethyl etherate / 4 h / 75 °C 2: boron trifluoride diethyl etherate; methanesulfonyl chloride / 2 h / 100 °C 3: boron tribromide / dichloromethane / 18 h / 60 °C View Scheme

C27H30O15 → orobol (480-23-9)

Conditions	Yield
With hydrogenchloride In water at 90℃; for 2h; Reflux;

5,7-dihydroxy-chromen-4-one (31721-94-5) → orobol (480-23-9)

Conditions

Yield

Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere 2: N-Bromosuccinimide; potassium acetate; acetic acid / 20 °C / Inert atmosphere 3: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate / N,N-dimethyl-formamide; water / 90 °C / Inert atmosphere 4: pyridine hydrochloride / 150 °C / Inert atmosphere View Scheme

4-oxo-4H-chromene-5,7-diyl diacetate → orobol (480-23-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; potassium acetate; acetic acid / 20 °C / Inert atmosphere 2: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate / N,N-dimethyl-formamide; water / 90 °C / Inert atmosphere 3: pyridine hydrochloride / 150 °C / Inert atmosphere View Scheme

3-bromo-4-oxo-4H-chromene-5,7-diyl diacetate → orobol (480-23-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate / N,N-dimethyl-formamide; water / 90 °C / Inert atmosphere 2: pyridine hydrochloride / 150 °C / Inert atmosphere View Scheme

orobol (480-23-9) + recombinant Escherichia coli expressing Streptomyces peucetius O-methyltransferase → 3',5,7-trihydroxy-4'-methoxyisoflavone (2284-31-3) + 3'-O-methylorobol (36190-95-1)

Conditions	Yield
With (R,S)-S-adenosyl-L-methionine In dimethyl sulfoxide at 40℃; for 24h; Enzymatic reaction;	A 33.3 mg B 27.9 mg

Upstream product

• 40316-84-5 3-(3,4-dimethoxyphenyl)-5,7-dimethoxychromen-4-one 
• 53084-11-0 3-(3,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one 
• 31721-94-5 5,7-dihydroxy-chromen-4-one 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 500-99-2 3,5-dimethoxyphenol 
• 552-58-9 eriodictyol 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 4419-11-8 2,2'-azobis-(2,4-dimethylvaleronitrile) 
• 20486-33-3 3',4',5,7-tetrahydroxyisoflavone β-D-glucopyranoside 
• 118949-94-3 6,8-di-C-β-D-glucopyranosyl-3',4',5,7-tetrahydroxyisoflavone 
• 66026-81-1 8-C-β-D-glucopyranosylorobol 

Downstream Products

• 2284-31-3 3',5,7-trihydroxy-4'-methoxyisoflavone 
• 36190-95-1 3'-O-methylorobol 

Relevant articles and documents

Reactions of genistein with alkylperoxyl radicals

Antioxidant actions of the soy isoflavone genistein are believed to contribute to its overall chemopreventive activity. However, the mechanisms of its antioxidant reactions remain unknown. The objective of this study was to characterize the reaction products of genistein (5,7,4'- trihydroxyisoflavone) with peroxyl radicals generated by thermolysis of 2,2'- azobis(2,4-dimethylvaleronitrile) (AMVN). Genistein oxidations with AMVN- derived peroxyl radicals yielded orobol (5,7,3',4'-tetrahydroxyisoflavone), a hydroxylated derivative of genistein, and several stable adducts of 4'- oxogenistein with AMVN-derived radicals. Some of these adducts include novel structures resulting from secondary oxidations of the AMVN-derived moiety. For all the observed oxidation products, the modifications occurred on the B- ring of the molecule. Genistein oxidation product structures provide potentially useful markers of genistein antioxidant chemistry.

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Comparative phytochemical analysis of four Mexican Nymphaea species

Four Mexican Nymphaea species, N. ampla, N. pulchella, N. gracilis and N. elegans belonging to subgenera Brachyceras were analyzed. In this work two 5-glycosyl isoflavones, 7,3′,4′-trihydroxy-5-O-β-d-(2″- acetyl)-xylopyranosylisoflavone (1) and 7,3′,4′-trihydroxy-5-O- α-l-rhamnopyranosylisoflavone (2), were isolated from N. ampla and N. pulchella, respectively, together with other known 3-glycosyl flavones and triterpene saponins from the same four species. The structures were elucidated by 1D and 2D NMR, FABMS, and other spectroscopic analyses. These results confirmed that the four species were different from each other and established that N. pulchella represents a different taxa than N. ampla. In addition, the 5-glycosyl isoflavones could be considered as a taxonomic character of this group of plants.

Phenolic constituents from the twigs of Betula schmidtii collected in Goesan, Korea

Six undescribed phenolic derivatives along with thirty two known compounds were isolated from the twigs of Betula schmidtii. The chemical structures were characterized through extensive spectroscopic analysis and chemical methods. All known compounds were first isolated in this plant. The anti-inflammatory effect of the isolates was tested by measuring nitric oxide production in lipopolysaccharide-activated BV-2 cells. Isotachioside, 4-allyl-2-hydrophenyl 1-O-β-D-apiosyl-(1 → 6)-β-D-glucopyranoside, genistein 5-O-β-D-glucoside, and prunetinoside showed a slight potency to lower the NO production against LPS-activated microglia with IC50 values of 23.9, 25.3, 28.8, and 34.0 μM, respectively.

CATECHOL DERIVATIVES PREPARED BY USING TYROSINASE, METHOD FOR PREPARATION THEREOF, AND APPLICATION THEREOF

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