574-12-9

Basic information

• Product Name: Isoflavone
• Synonyms: 3-Phenylchromen-4-one;3-phenyl-4h-1-benzopyran-4-one;ISOFLAVONE;ISOFLAVONE (SOY BEAN);3-Phenylchromone;Soy Isoflavones P.E;BioaActive Soy Isoflavones;Nanoactive Soy Isoflavones
• CAS NO: 574-12-9
• Molecular Formula: C15H10O2
• Molecular Weight: 222.24
• EINECS: 1308068-626-2
• Product Categories: Plant extracts;Herb extract
• Mol File: 574-12-9.mol
• Article Data: 56

Chemical Properties

• Melting Point: 148°
• Boiling Point: 323.41°C (rough estimate)
• Flash Point: 171.1 °C
• Appearance: /
• Density: 1.1404 (rough estimate)
• Vapor Pressure: 1.41E-05mmHg at 25°C
• Refractive Index: 1.6600 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Isoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: Isoflavone(574-12-9)
• EPA Substance Registry System: Isoflavone(574-12-9)

Safety Data

• Hazardous Substances Data: 574-12-9(Hazardous Substances Data)

Usage

Main effects

Isoflavones are non-nutritive botanical compounds that are rich in soy products and a few other plant species; both genistein and ?glycetein are isoflavones. Their chemical structure looks similar to estrone (also known as estrogen), a steroid hormone. Plant sources: produced mainly from soybeans, lentils, pod legumes s well as highly processed food made from soybeans such as vegetarian meat, soybean flour, tofu and soy milk. Among them, tofu retains more of isoflavone content than milk. Main functions of isoflavones： Reduce LDL cholesterol, help to prevent or cure menopausal syndromes and provide the linoleic acid and linoloinic acid needed by human body. Balance blood cholesterol and reduce blood cholesterol levels. Make arteries more flexible and prevent damage to heart Enhance bone density, reduce calcium loss and reduce the chance of suffering from osteoporosis. Reduce the chance of suffering from cancer, especially breast cancer and prostate cancer. Relieve menopause discomfort, such as hot flash, fever, emotional instability, headache, insomnia, fatigue, night sweats, vaginal dryness and so on. Treat Enteritis syndrome, hot flash, osteoporosis, cardiovascular disease and cancer, also help fight coronary heart disease. Flavonoids can reduce the formation of free radicals and help regeneration of other antioxidants. Soy isoflavones are a type of natural plant estrogen which is good to human body. The plant bioactive element extracted from natural soybeans is very similar to the estrogen molecular structure and can be combined with female estrogen receptors and play two-ways regulation on estrogen safely and with no side effects, so it is also known as "phytoestrogen." It can relieve osteoporosis and other symptoms caused by menopause, delay skin aging, improve skin quality, make female skin smooth, delicate and elastic. Due to its role in improvement of women life quality, it is also called "feminine charm factor".

Isomers of flavonoids

Isoflavones are isomers of flavones with some physiological activity.The phenyl group side chain of its γ-pyrazone ring is not connected to C2 position but to C3 position. Natural isoflavones are mainly found in angiosperms and some members of the Fabaceae Rosaceae and Iridaceae family. The kudzu root, one of the legume contains five isoflavone derivatives, namely, glycinin, daidzein, puerarin, puerarin- 7-xyloside and daidzein-4 ', 7-diglucoside. The structure of isoflavones compound are similar to that of estrogen, so generally it is regarded as the precursor substances of hormone, and it differs from flavonoids compound in its negative reaction against hydrochloric acid and magnesium powder.

Uses

Different sources of media describe the Uses of 574-12-9 differently. You can refer to the following data:
1. Antioxygenation, estrogen-like, cancer prevention and anti-cancer, disease prevention such as senile dementia, cardiovascular diseases and breast cancer, improvement of life quality.
2. Isoflavones possess antioxidant properties and antipromotional effects.

Definition

ChEBI: A simplest member of the class of isoflavones that is 4H-chromen-4-one in which the hydrogen at position 3 is replaced by a phenyl group.

InChI:InChI=1/C15H10O2/c16-15-12-8-4-5-9-14(12)17-10-13(15)11-6-2-1-3-7-11/h1-10H

Synthetic route

2-hydroxy-deoxybenzoin (2491-31-8) → isoflavone (574-12-9)

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

3-iodo-chromen-4-one (122775-34-2) + phenylboronic acid (98-80-6) → isoflavone (574-12-9)

Conditions	Yield
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%

isoflavanone (97904-75-1, 4737-27-3, 143358-19-4, 143358-34-3) → isoflavone (574-12-9)

Conditions	Yield
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%

2-hydroxy-deoxybenzoin (2491-31-8) + orthoformic acid triethyl ester (122-51-0) → isoflavone (574-12-9)

Conditions	Yield
With dmap at 100℃; for 4h;	96%
With piperidine; pyridine for 8h; Heating;	91%

3-(2-bromophenyl)-3-oxo-2-phenylpropanal (1258792-30-1) → isoflavone (574-12-9)

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

3-phenyl-3-(phenylsulfonyl)chroman-4-one (140870-46-8) → isoflavone (574-12-9)

Conditions	Yield
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature;	95%

3-bromo-4H-chromen-4-one (49619-82-1) + phenylboronic acid (98-80-6) → isoflavone (574-12-9)

Conditions	Yield
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%

Flavanone (487-26-3) → isoflavone (574-12-9)

Conditions	Yield
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%

2-hydroxy-deoxybenzoin (2491-31-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → isoflavone (574-12-9)

Conditions	Yield
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;

Upstream product

• 2491-31-8 2-hydroxy-deoxybenzoin 
• 109-94-4 formic acid ethyl ester 
• 77287-34-4 formamide 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 487-26-3 Flavanone 
• 192440-12-3 1-(2-hydroxyphenyl)-2-phenyl-2-propen-1-one 
• 42772-82-7 1-(2-Hydroxyphenyl)-2-phenylpropan-1-one 
• 59564-29-3 3-(2-hydroxyphenyl)-4-phenylisoxazole 
• 108-24-7 acetic anhydride 
• 38111-44-3 phenylzinc(II) bromide 
• 122775-34-2 3-iodo-chromen-4-one 
• 491-38-3 1-benzopyran-4(4H)-one 
• 13400-26-5 3-hydroxychromen-4-one 

Downstream Products

• 7622-78-8 4-oxo-3-phenyl-4H-1-benzopyran-2-carboxylic acid 
• 82381-50-8 2-((Z)-1-Ethyl-3-hydroxy-2-phenyl-pent-1-enyl)-phenol 
• 64139-00-0 4-phenyl-5-(2-hydroxyphenyl)isoxazole 
• 75989-83-2 2,3-dichloro-3-phenylchroman-4-one 
• 1427272-78-3 3-cyano-6-(2-hydroxylphenyl)-5-phenylpyridine-2(1H)-thione 
• 60188-52-5 3-(2-hydroxyphenyl)-4-phenyl-1H-pyrazole 
• 1362858-72-7 (3R)-3-phenyl-2,3-dihydro-4H-1-benzopyran-4-one 

Relevant articles and documents

Rhodium complexes catalyze oxidative coupling between salicylaldehyde and phenylacetylene via C-H bond activation

A coupling reaction between salicylaldehyde and phenylacetylene was catalyzed by well-defined rhodium complexes, Rh(cod)(l-amino acid) (cod is 1,5-cyclooctadiene; l-amino acid is l-proline, l-phenylalanine and l-valine), to give a flavonoid in 40-88% yield, providing a method for flavonoid synthesis. The coupling reactions catalyzed by Rh(cod)(l-amino acid)s gave higher yields than those by [Rh(cod)Cl]2 without l-amino acid ligands. The reaction mechanism may be that l-amino acid ligands of the rhodium complexes can provide an empty track for phenylacetylene to form a ring structure that fractures to produce the aim flavonoid and RhIX species. Then, the active RhIX specie is oxidized to regenerate RhIIIX3 by Cu(OAC)2.

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.

Ionic liquids and ohmic heating in combination for Pd-catalyzed cross-coupling reactions: Sustainable synthesis of flavonoids

In order to meet the increasing demand for environmentally benign chemical processes, we developed a Suzuki-Miyaura reaction protocol based on the combination of ohmic heating (?H) and supported ionic liquid phase catalysis (SILPC) in aqueous media. This methodology was applied to the synthesis of a series of flavonoid derivatives, including isoflavones, styrylisoflavones, and diarylalkenylisoflavones.