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574-12-9

Basic Information
CAS No.: 574-12-9
Name: Isoflavone
Article Data: 66
Cas Database
Molecular Structure:
Molecular Structure of 574-12-9 (Isoflavone)
Formula: C15H10O2
Molecular Weight: 222.243
Synonyms: Isoflavone(6CI,7CI,8CI);3-Phenyl-4-chromone;3-Phenylchromone;Isoflavone 80;NSC 135405;4H-1-Benzopyran-4-one,3-phenyl-;
EINECS: 611-522-9
Density: 1.239 g/cm3
Melting Point: 150oC
Boiling Point: 367 °C at 760 mmHg
Flash Point: 171.1 °C
Solubility: N/A
Appearance: N/A
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 30.21000
LogP: 3.46000
Synthetic route
2491-31-8

2-hydroxy-deoxybenzoin

574-12-9

isoflavone

Conditions
ConditionsYield
With methanesulfonyl chloride In N,N-dimethyl-formamide at 60 - 70℃; for 1h;98%
122775-34-2

3-iodo-chromen-4-one

98-80-6

phenylboronic acid

574-12-9

isoflavone

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene for 15h; Heating;97.8%
With sodium carbonate; palladium on activated charcoal In 1,2-dimethoxyethane; water at 25℃; for 12h; Suzuki-Miyaura cross-coupling;95%
With palladium diacetate; sodium carbonate In methanol at 50℃; for 3h; Suzuki Coupling;95%
Conditions
ConditionsYield
With sulfuric acid; iodine; dimethyl sulfoxide at 100℃; for 0.5h;97%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethylsulfoxide-d6 at 85℃; for 48h;45%
2491-31-8

2-hydroxy-deoxybenzoin

122-51-0

orthoformic acid triethyl ester

574-12-9

isoflavone

Conditions
ConditionsYield
With dmap at 100℃; for 4h;96%
With piperidine; pyridine for 8h; Heating;91%
3-(2-bromophenyl)-3-oxo-2-phenylpropanal
1258792-30-1

3-(2-bromophenyl)-3-oxo-2-phenylpropanal

574-12-9

isoflavone

Conditions
ConditionsYield
With 2-Picolinic acid; copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 135 - 140℃; for 20h; Inert atmosphere;96%
140870-46-8

3-phenyl-3-(phenylsulfonyl)chroman-4-one

574-12-9

isoflavone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature;95%
49619-82-1

3-bromo-4H-chromen-4-one

98-80-6

phenylboronic acid

574-12-9

isoflavone

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; benzene for 6h; Heating;94%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In benzene for 53h; Hoshino-Suzuki-Miyaura coupling; Reflux; Inert atmosphere;94%
With potassium carbonate; (1-benzothiazol-2-yl-ethanone oxime)dichloropalladium(II) In toluene at 150℃; for 0.133333h; Suzuki-Miyaura cross-coupling; microwave irradiation;93%
487-26-3

Flavanone

574-12-9

isoflavone

Conditions
ConditionsYield
With thallium(III) acetate; toluene-4-sulfonic acid In various solvent(s)94%
With thallium(III) toluene-p-sulfonate In various solvent(s) for 3h; Heating;94%
With thallium(III) perchlorate In water; acetonitrile for 0.333333h; Heating;94%
2491-31-8

2-hydroxy-deoxybenzoin

68-12-2, 33513-42-7

N,N-dimethyl-formamide

574-12-9

isoflavone

Conditions
ConditionsYield
With dmap at 100℃; for 4h;92%
Stage #1: 2-hydroxy-deoxybenzoin With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: N,N-dimethyl-formamide With trichlorophosphate In tetrahydrofuran at 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 1h;
80%
With boron trifluoride diethyl etherate; methanesulfonyl chloride at 110℃; for 21h; Yield given;
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Specification

1. Introduction of Isoflavone
Isoflavone is one kind of light yellow powder or off yellow or yellow powder. Its IUPAC Name is 3-phenylchromen-4-one. Isoflavone is highly soluble in water. It also can be called Isoflavone; NSC 135405; 4H-1-Benzopyran-4-one, 3-phenyl- (9CI); Isoflavone (8CI).

2. Properties of Isoflavone
Physical properties about Isoflavone are:
(1)Index of Refraction: 1.635; (2)Molar Refractivity: 64.2 cm3; (3)Molar Volume: 179.2 cm3; (4)Polarizability: 25.45×10-24 cm3; (5)Surface Tension: 49.5 dyne/cm; (6)Density: 1.239 g/cm3; (7)Flash Point: 171.1 °C; (8)Enthalpy of Vaporization: 61.35 kJ/mol; (9)Boiling Point: 367 °C at 760 mmHg; (10)Vapour Pressure: 1.41E-05 mmHg at 25°C; (11)XLogP3-AA: 3.2; (12)H-Bond Donor: 0; (13)H-Bond Acceptor: 2; (14)Rotatable Bond Count: 1; (15)Exact Mass: 222.06808; (16)MonoIsotopic Mass: 222.06808; (17)Topological Polar Surface Area: 26.3; (18)Heavy Atom Count: 17; (19)Formal Charge: 0; (20)Complexity: 326; (21)Isotope Atom Count: 0; (22)Defined Atom Stereocenter Count: 0; (23)Undefined Atom Stereocenter Count: 0; (24)Defined Bond Stereocenter Count: 0; (25)Undefined Bond Stereocenter Count: 0; (26)Covalently-Bonded Unit Count: 1; (27)Feature 3D Acceptor Count: 2; (28)Feature 3D Ring Count: 3; (29)Effective Rotor Count: 1; (30)Conformer Sampling RMSD: 0.6.

3. Structure Descriptors of Isoflavone
(1)Canonical SMILES: C1=CC=C(C=C1)C2=COC3=CC=CC=C3C2=O
(2)InChI: InChI=1S/C15H10O2/c16-15-12-8-4-5-9-14(12)17-10-13(15)11-6-2-1-3-7-11/h1-10H
(3)InChIKey: GOMNOOKGLZYEJT-UHFFFAOYSA-N
(4)Smiles: c1(c(c2ccccc2oc1)=O)c1ccccc1

4. Uses of Isoflavone
Isoflavones comprise a class of organic compounds, often naturally occurring, related to the isoflavonoids. It can be used as medicine additives, functional food additives,cosmetic additives etc. Besides, Isoflavone is applied in food field,health product field,cosmetics field,pharmaceutical field.