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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Isoflavone is a natural product derived from the Fabaceae family with potential phytoestrogenic, cholesterol-reducing, chemotherapeutic and antioxidant activity.
Synonyms: 3-Phenylchromone; NSC 135405
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 574-12-9 |
Formula : | C15H10O2 |
M.W : | 222.24 |
SMILES Code : | O=C1C(C2=CC=CC=C2)=COC3=C1C=CC=C3 |
Synonyms : |
3-Phenylchromone; NSC 135405
|
MDL No. : | MFCD00100851 |
InChI Key : | GOMNOOKGLZYEJT-UHFFFAOYSA-N |
Pubchem ID : | 72304 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With tetrabutylammomium bromide; sodium carbonate; In water; at 100℃; for 1h;Green chemistry; | General procedure: A mixture of the corresponding bromochromone1(0.50 mmol), the corresponding boronic acid2(0.60 mmol), Na2CO3(0.50 mmol) andPdSILP(0.05% mmol of Pd) in H2O was stirred under ohmic heating at 100 C for 1 h. The catalyst was filtered-off and the filtrate was extracted with Et2O (3 × 10 mL). The combined extracts were dried over Na2SO4and evaporated under reduced pressure affording products3. The physical data of known isoflavones3a-fwere comparable to those of the literature [34,35,36,37,38]. The physical data of the new isoflavones3g-jare shown below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With palladium 10% on activated carbon; sodium carbonate; In 1,2-dimethoxyethane; water; at 45℃; for 4h; | General procedure: The iodochromones (1 equiv.) were suspended in dimethoxyethane/water (1:1) and stirred at room temperature. Sodium carbonate (3.0 equiv.) was added followed by the appropriate boronic acid (1.2 equiv.). 10 % Pd/C (5 mol %) was added and the reaction mixture stirred at 45C for 4h. The reaction mixture was filtered through a short pad of celite. The catalyst was washed using water and dichloromethane and the filtrate partitioned into dichloromethane. The organic fraction was dried using anhydrous sodium sulphate and the solvent evaporated in vacuo. The crude product was subjected to flash chromatography eluted using n-hexanes and ethyl acetate. -phenyl-4H-chrome-4-one (15) White solid (43mg, 90%) m.p. 129C, Rf (EtOAc: Hexane 2:8) 0.37, 1H NMR (400 MHz, CDCl3) delta 8.33 (d, J = 8.0 Hz, 1H, H-5), 8.03 (s, 1H, H-2), 7.69 (m, 1H, Ar-H), 7.58 (m, 2H, Ar-H), 7.44 (m, 5H, Ar-H). 13C NMR (101 MHz, CDCl3) delta 176.2, 156.3, 153.0, 133.6, 131.9, 129.0, 129.0, 128.5, 128.2, 126.5, 125.5, 125.3, 124.7, 118.0 m/z (LRMS, EI) Found 222 (M+) C15H10O2 requires M, 222.07. HPLC 99 % (Method B, tR 10.64min) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
ISOLATION OF ISOFLAVONE FROM AQUEOUS PLANT EXTRACTS EXAMPLE 1 The aqueous plant extract from Preparation 1 (100 mL) was adjusted to pH 11.2 using 6 N NaOH. The aqueous phase was then extracted with 1-butanol (100 mL) and the layers separated. The pH of the aqueous phase was adjusted to 6.8 using concentrated HCl and was re-extracted with 1-butanol (60 mL) to yield a second extract. The first extract upon concentration under reduced pressure yielded 1.28 g of yellow solid (3.37% isoflavones), and the second extract upon likewise treatment yielded 0.55 g of pale yellow solid (purity 37.78%, recovery: 56.9%). | ||
EXAMPLE 19 Preparation of 2-Carboxy-5-Hydroxy-7-(1-Deoxy-1-alpha-Fucosyl-Ethyleneoxy)-4-Methoxy Isoflavone (54) A solution of 2-carboethoxy-5,7-dihydroxy-4'-methoxy-isoflavone (52, 166 mg, 0.47 mmole) and the iodide 48 (200 mg, 0.47 mmole) in dimethylforamide (1 ml) was stirred with potassium carbonate (265 mg) for 14 hours. The mixture was worked up with water (50 ml) and ethyl acetate (2*100 ml). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was purified on a silica gel column (hexane:ethyl acetate, 1:1) to provide the isoflavone 53 (265 mg, 86%). | ||
The represented compounds of the formula (I) are disclosed below: ... (26) 7-(4-Chlorobenzyl)oxy-3-phenyl-4H-1-benzopyran-4-one (27) 7-(4-Nitrobenzyl)oxy-2-methyl-3-phenyl-4H-1-benzopyran-4-one (28) 7-(2-Hydroxyethoxy)-3-phenyl-4H-1-benzopyran-4-one (29) 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (30) 3-Phenyl-4H-1-benzopyran-4-one (31) 2,7-Dihydroxy-3-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one (32) 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (33) 5,6-Dihydroxy-7-methoxy-3-(5-hydroxy-3,4-dimethoxyphenyl)-4H-1-benzopyran-4-one ... |
(c) Benzyl-2-hydroxyphenyl ketone (29.0 g) and formamide (29.0 g). were heated together at 208 for 1 hr. The reaction mixture was cooled and diluted with water. The oily product was extracted into chloroform and the solution washed with water, dried and evaporated. The residue was chromatographed on alumina, eluding with toluene, and the product recrystallized once from petroleum ether (80-100) and once from toluene to yield isoflavone (3.55 g), m.pt. 132-134 | ||
Comparative Example 2 Extraction with high concentration of ethanol An isoflavone fraction was obtained in the same way as in Example 1 except that the concentration of aqueous ethanol used for elution of isoflavones from a column was 70% by volume. The fraction was concentrated under reduced pressure at 60C, dried and powdered to obtain 30 g of an isoflavone-containing composition. The isoflavone concentration of the obtained isoflavone-containing composition was 20.7% by weight of the total solid content. The saponin concentration was 33% by weight of the total solid content. |