5,7-二羟基-4ˊ-甲氧基异黄酮
Biochanin A
CAS: 491-80-5
Molecular Formula: C16H12O5
5,7-二羟基-4ˊ-甲氧基异黄酮 - Names and Identifiers
| Name | Biochanin A |
| Synonyms | BIOCHANIN Biochanin A Biochani,Olmelin BIOCHANIN A (AHP) 5,7-Dihydroxy-4'-methoxyisoflavone 5,7-Dihydrox -4'-Methoxyisoflavone 5,7-Dihydrox -4'-methoxyisoflavone 5,7-dihydroxy-4'-methoxy-Isoflavone 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-on 5,7-Dihydroxy-3-(4-méthoxyphényl)-4H-chromén-4-one 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one 4H-1-benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)- Biochanin A, (5,7-Dihydroxy-4'-methoxyisoflavone) |
| CAS | 491-80-5 |
| EINECS | 207-744-7 |
| InChI | InChI=1/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3 |
5,7-二羟基-4ˊ-甲氧基异黄酮 - Physico-chemical Properties
| Molecular Formula | C16H12O5 |
| Molar Mass | 284.26 |
| Density | 1.420±0.06 g/cm3(Predicted) |
| Melting Point | 210-213°C(lit.) |
| Boling Point | 340-355 °C(Press: 0.5 Torr) |
| Flash Point | 198.2°C |
| Water Solubility | Soluble in water (<1 mg/ml at 25°C), chloroform, methanol, DMSO (57 mg/ml at 25°C), and ethanol (9 mg/ml at 25°C). |
| Solubility | Soluble in DMSO, chloroform and methanol mixed solvent, hot methanol, insoluble in petroleum ether, chloroform and other solvents. |
| Vapor Presure | 2.25E-11mmHg at 25°C |
| Appearance | White needle crystal |
| Color | Off-White to Beige |
| Maximum wavelength(λmax) | 263nm(EtOH)(lit.) |
| BRN | 278107 |
| pKa | 6.50±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.668 |
| MDL | MFCD00006839 |
| Physical and Chemical Properties | White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from red clover, chickpea (Cicer arietinum L.) seeds. |
| In vitro study | Biochanin A was reported to inhibit epidermal growth factor receptor protein tyrosine kinase (PTK) with an IC50 value of 91.5 μm. Biochanin A inhibited the hydrolysis of 0.5 μm cannabinoids by fatty acid amide (FAAH) in mice, rats and humans with IC50 values of 1.8,1.4 and 2.4 μm, respectively. Biochanin A was able to inhibit the growth of serum and EGF-stimulated LNCaP and DU-145 cells (IC50 values for serum ranged from 8.0 to 27 μg/ml, IC50 values for EGF ranged from 4.3 to 15 μg/ml), but had no significant effect on the autophosphorylation of EGF receptor tyrosine. |
| In vivo study | LD50: Mouse 63 mg/kg (I. P.) |
5,7-二羟基-4ˊ-甲氧基异黄酮 - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | DJ3002500 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29329990 |
5,7-二羟基-4ˊ-甲氧基异黄酮 - Reference
| Reference Show more | 1. Hao Yu, Liu Chunming, Li Sainan, etc. Screening of bioactive ligands from Trifolium pratense by affinity ultrafiltration mass spectrometry [J]. Northern horticulture 2019 000(017):102-107. 2. Li, Hong-Fu, et al. "Global Profiling and Structural Characterization of Metabolites of Onin Using HPLC-ESI-IT-TOF-MS n After Oral Administration to Rats." Journal of Agricultural and Food Chemistry 68.51 (2020): 15164-15175.https:// doi.org/10.1021/acs.j 3. [IF = 7.514] Yuping Zhang et al."Integration of magnetic solid phase fishing and off-line two-dimensional high-performance liquid chromatography-diode array detector-mass spectrometry for screening and identification of human serum albumin binders from Radix Astragali 4. [IF=3.645] Wenjie Wu et al."Simple, rapid, and environmentally friendly method for the separation of isoflavones using ultra-high performance supercritical fluid chromatography."J Sep Sci. 2017 Jul;40(13):2827-2837 5. [IF=5.279] Hong-Fu Li et al."Global Profiling and Structural Characterization of Metabolites of Ononin Using HPLC-ESI-IT-TOF-MSn After Oral Administration to Rats."J Agr Food Chem. 2020;68(51):15164-15175 6. [IF=4.769] Jing Han et al."Qualitative and quantitative evaluation of Flos Puerariae by using chemical fingerprint in combination with chemometrics method."J Pharm Anal. 2021 Sep;: 7. [IF=4.759] Wenjie Wu et al."An analytical strategy for accurate, rapid and sensitive quantitative analysis of isoflavones in traditional Chinese medicines using ultra-high performance supercritical fluid chromatography: Take Radix Puerariae as an example."J Chromato 8. [IF=6.576] Junkun Pan et al."Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure-Activity Relationship, Kinetics and Interaction Mechanism."Frontiers in Nutrition. 2022; 9: 892426 |
5,7-二羟基-4ˊ-甲氧基异黄酮 - Introduction
Pharmacological effects: It has estrogen-like effects, can inhibit the increase of cholesterol, and also has anti-fungal and anti-tumor effects. It has a bidirectional regulatory effect on hormone levels in the human body. There is also anti-cancer, antispasmodic and hypolipidemic effect.
Last Update：2022-10-16 17:25:26
5,7-二羟基-4ˊ-甲氧基异黄酮 - Reference Information
| introduction | chickpea sprout A(Biochanin A,BCA) is an oxymethylated isoflavone compound, which is widely found in some edible plants, such as soybean, red clover, alfalfa, peanut and chickpea, especially red clover, but it is only 833mg/100g. |
| Application | The molecular structure of BCA is similar to that of animal estrogen, and it can competitively bind to estrogen receptors and exert estrogen-like effects. It is an important phytoestrogen and has beneficial effects on human and animal health in many aspects, it can be used for the prevention and treatment of osteoporosis, menopausal syndrome and other diseases. In addition, it also has anti-tumor, anti-inflammatory, antibacterial, hypoglycemic, antioxidant, neuroprotective and other pharmacological effects. |
| preparation | CN201610575057.3 provides a synthesis method of chickpea sprout A, which mainly solves the problems of complicated synthesis process and low yield in the prior art. Including the following steps: Step 1 The preparation of the intermediate is at room temperature, adding phosphorus oxychloride to phloroglucinol, p-methoxyphenylacetonitrile and isopropyl ether, and after the reaction is complete, adding an appropriate amount of water to hydrolyze, Using activated carbon to decolorise, the intermediate is obtained; step 2 preparation of crude product The intermediate and methylsulfonyl chloride obtained in step 1 are cyclically generated into chickpea sprout A crude product in N,N-dimethylformamide (DMF); step 3 Refining The crude chickpea sprout A obtained in step 2 is recrystallized with ethanol and decolorized with activated carbon to obtain chickpea sprout A. The synthetic route of the present invention is as follows: |
| biological activity | Biochanin A (4-Methylgenistein) is O-methyl isoflavone and is a natural organic compound of flavonoids. |
| target | TargetValue FAAH (rat) 1.4 μM FAAH (mouse) 1.8 μM FAAH (human) 2.4 μM EGFR 91.5 μM |
| Target | Value |
| FAAH (rat) | 1.4 μM |
| FAAH (mouse) | 1.8 μM |
| FAAH (human) | 2.4 μM |
| EGFR | <91.5 μM |
| in vitro study | Biochanin a was reported to be a protein tyrosine kinase (PTK) capable of inhibiting epidermal growth factor receptor with an IC50 value of 91.5 μM. Biochanin A inhibited the hydrolysis of 0.5 μM cannabinoid by fatty acid amide (FAAH) in mice, rats and humans. IC50 values were 1.8,1.4 and 2.4 μM respectively. Biochanin A can inhibit the growth of LNCaP and DU-145 cells stimulated by serum and EGF (IC50 values for serum are 8.0 to 27 μg/ml, and IC50 values for EGF are 4.3 to 15 μg/ml), but it has no significant effect on EGF receptor tyrosine autophosphorylation. |
| in vivo study | LD50: mouse 63 mg/kg (intraperitoneal injection) |
| chemical properties | white crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from red clover, chickpea (Cicer arietinum L.) seeds. |
| use | has estrogen-like effect, can inhibit the increase of cholesterol, and also has antifungal and antitumor effects. It has a bidirectional regulatory effect on hormone levels in the human body. There is also anti-cancer, antispasmodic and hypolipidemic effect. |
| EPA chemical information | information provided by: ofmpub.epa.gov (external link) |
Last Update：2024-04-09 21:11:58
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View History
5,7-二羟基-4ˊ-甲氧基异黄酮
反-4-氨基环己甲酸甲酯盐酸盐
4-(HYDROXYMETHYL)PICOLINITRILE
三氟甲基磺酸锂
Dimethyl Carbitol
L-樟脑酸
6ALPHA-DEOXY-6ALPHA-AZIDO-4ALPHA-DEOXY-4ALPHA-(THYMIN-1-YL)-2,3ALPHA:2ALPHA,5ALPHA-DIANHYDRO-L-ALTROFURANOSE DIMETHYL ACETAL
6-氯-3-氰基邻二氮杂苯
N-(tert-Butyloxycarbonyl)glutamic acid 5-tert-butyl ester
TRANS-O-METHYL-O-COUMARIC ACID
反-4-氨基环己甲酸甲酯盐酸盐
4-(HYDROXYMETHYL)PICOLINITRILE
三氟甲基磺酸锂
Dimethyl Carbitol
L-樟脑酸
6ALPHA-DEOXY-6ALPHA-AZIDO-4ALPHA-DEOXY-4ALPHA-(THYMIN-1-YL)-2,3ALPHA:2ALPHA,5ALPHA-DIANHYDRO-L-ALTROFURANOSE DIMETHYL ACETAL
6-氯-3-氰基邻二氮杂苯
N-(tert-Butyloxycarbonyl)glutamic acid 5-tert-butyl ester
TRANS-O-METHYL-O-COUMARIC ACID