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574-12-9

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574-12-9 Usage

Description

Isoflavone is a naturally occurring compound belonging to the class of isoflavones, characterized by its 4H-chromen-4-one structure with a phenyl group replacing the hydrogen at position 3. It is known for its antioxidant properties, estrogen-like effects, and various health benefits.

Uses

Used in Antioxidation:
Isoflavone is used as an antioxidant agent for its ability to neutralize free radicals and prevent oxidative damage to cells, which can lead to various diseases and aging.
Used in Hormone Regulation:
Isoflavone is used as an estrogen-like substance for its ability to mimic the effects of estrogen in the body, which can be beneficial for hormone regulation and maintaining a balanced hormonal state.
Used in Cancer Prevention and Treatment:
Isoflavone is used as a cancer prevention and anti-cancer agent due to its antioxidant and antipromotional effects, which can help reduce the risk of developing cancer and inhibit the growth of cancer cells.
Used in Disease Prevention:
Isoflavone is used in the prevention of various diseases, such as senile dementia, cardiovascular diseases, and breast cancer, due to its antioxidant and estrogen-like properties, which can help protect against these conditions.
Used in Quality of Life Improvement:
Isoflavone is used to improve the quality of life by promoting overall health and well-being through its various health benefits, including antioxidant, estrogen-like, and disease prevention properties.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 574-12-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 4 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 574-12:
(5*5)+(4*7)+(3*4)+(2*1)+(1*2)=69
69 % 10 = 9
So 574-12-9 is a valid CAS Registry Number.
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

574-12-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name isoflavone

1.2 Other means of identification

Product number -
Other names 3-Phenyl-4H-chromen-4-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:574-12-9 SDS

574-12-9Synthetic route

2-hydroxy-deoxybenzoin
2491-31-8

2-hydroxy-deoxybenzoin

isoflavone
574-12-9

isoflavone

Conditions
ConditionsYield
With methanesulfonyl chloride In N,N-dimethyl-formamide at 60 - 70℃; for 1h;98%
3-iodo-chromen-4-one
122775-34-2

3-iodo-chromen-4-one

phenylboronic acid
98-80-6

phenylboronic acid

isoflavone
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%
2-hydroxy-deoxybenzoin
2491-31-8

2-hydroxy-deoxybenzoin

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

isoflavone
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

isoflavone
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%
3-phenyl-3-(phenylsulfonyl)chroman-4-one
140870-46-8

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

isoflavone
574-12-9

isoflavone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature;95%
3-bromo-4H-chromen-4-one
49619-82-1

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

phenylboronic acid
98-80-6

phenylboronic acid

isoflavone
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%
Flavanone
487-26-3

Flavanone

isoflavone
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%
2-hydroxy-deoxybenzoin
2491-31-8

2-hydroxy-deoxybenzoin

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

isoflavone
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;

574-12-9Relevant articles and documents

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

Jia, Hongge,Tang, Yanan,Shi, Yongqiang,Ma, Liqun,He, Zijian,Lai, Weiwei,Yang, Yi,Wang, Yazhen,Zang, Yu,Xu, Shuangping

, p. 1791 - 1795 (2017)

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.

Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

Chang, Ya-Ting,Liu, Ling-Jun,Peng, Wen-Sheng,Lin, Lin-Ting,Chan, Yi-Tsu,Tsai, Fu-Yu

, p. 469 - 475 (2021/02/03)

Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.

The oxidative coupling between benzaldehyde derivatives and phenylacetylene catalyzed by rhodium complexes via C-H bond activation

Jia, Hongge,Ma, Liqun,Shi, Yongqiang,Song, Heming,Tang, Yanan,Wang, Qingji,Wang, Yazhen,Xu, Shuangping,Yang, Guoxing,Zang, Yu,Zhao, Xinyi

, p. 20 - 25 (2020/03/30)

This paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation. These reactions were catalyzed by Rh(l-amino acid)(cod) (the l-amino acid is l-phenylala

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