ipriflavone

ipriflavone - Names and Identifiers

Name	ipriflavone
Synonyms	tc80 osten osteofix Ipriavone Ipriflavon Iprflavone ipriflavone IPRIFLAVONE(P) 7-Isopropoxyisoflavone 3-phenyl-7-(propan-2-yloxy)-4H-chromen-4-one 2-phenyl-7-(propan-2-yloxy)-4H-chromen-4-one
CAS	35212-22-7
EINECS	609-092-2
InChI	InChI=1/C18H16O3/c1-12(2)21-14-8-9-15-17(10-14)20-11-16(18(15)19)13-6-4-3-5-7-13/h3-12H,1-2H3
InChIKey	SFBODOKJTYAUCM-UHFFFAOYSA-N

ipriflavone - Physico-chemical Properties

Molecular Formula	C18H16O3
Molar Mass	280.32
Density	1.2170 (rough estimate)
Melting Point	116-120°C(lit.)
Boling Point	363.04°C (rough estimate)
Flash Point	209.3°C
Vapor Presure	8.47E-08mmHg at 25°C
Appearance	powder to crystal
Color	White to Almost white
Merck	14,5074
Storage Condition	Sealed in dry,Room Temperature
Refractive Index	1.4700 (estimate)
MDL	MFCD00221719
Physical and Chemical Properties	White to yellowish white crystals or crystalline powder, odorless and tasteless. Soluble in chloroform or dimethylformamide, more soluble in acetonitrile, acetone or ethyl acetate, more difficult to dissolve in methanol, ethanol or anhydrous ether, very difficult to dissolve in hexane, a few insoluble in water. The melting point was 115-117 °c. Acute toxicity LD50 mice and rats (mg/kg):>10000 oral,>2500 intraperitoneal and subcutaneous.
In vitro study	Ipriflavone can regulate the differentiation and biosynthesis properties of human bone marrow stromal osteoprogenitor cells (BMC) by enhancing the expression of certain important matrix proteins and promoting the mineralization process. Treatment with Ipriflavone at a dose of 10 μm significantly inhibited glycosylation end product (AGE) enhanced bone resorption in cultured mouse undifferentiated bone cells. In addition, Ipriflavone treatment was able to effectively enhance calcium absorption by duodenal cells. Ipriflavone dose-dependently inhibited proliferation and DNA synthesis of MDA-231 cells and blocked ligand-induced phosphorylation of Tyr845 in EGFR. Treatment with Ipriflavone at a dose of 50 μm did not cause apoptosis of MDA-231 cells.
In vivo study	For bone metastases, Ipriflavone, administered orally at a dose of 12 mg instead of 6 mg, significantly inhibits the development of new osteolytic bone metastases of MDA-231 cells and inhibits the progression of established osteolytic lesions, and reduce the number of osteoclasts adjacent to cancer cells. Consistent with in vitro activity, Ipriflavone treatment at doses of 6 or 12 mg/kg significantly inhibited tumor growth in MDA-231 xenografts compared to untreated mice, the treated mice were reduced by 25% and 45% in volume and 47% and 63% in weight, respectively, and the life span of tumor-bearing mice was prolonged. LD50: mice> 2.5 g/kg (intraperitoneal injection),>5 g/kg (subcutaneous injection),>10 g/kg (Gavage); rats> 2.5 g/kg (intraperitoneal injection),>5 g/kg (subcutaneous injection),>10 g/kg (Gavage)

ipriflavone - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S24/25 - Avoid contact with skin and eyes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany	2
RTECS	DJ3100500
HS Code	29329990

ipriflavone - Nature

Open Data Verified Data

white to yellowish white crystal or crystalline powder, odorless and tasteless. The melting point was 115-117 °c. Soluble in chloroform or dimethylformamide, more soluble in acetonitrile, acetone or ethyl acetate, more difficult to dissolve in methanol, ethanol or anhydrous ether, very difficult to dissolve in hexane, almost insoluble in water.

Last Update：2024-01-02 23:10:35

ipriflavone - Preparation Method

Open Data Verified Data

anhydrous zinc chloride was dissolved in anhydrous ether and resorcinol was added. With stirring and cooling in an ice bath, dry hydrogen chloride gas was introduced to saturation, and phenylacetonitrile was added slowly with stirring, and then hydrogen chloride was passed through and allowed to stand. The upper ether layer was poured off, hydrochloric acid was added, and the mixture was stirred for a while. After standing, the upper layer of acid solution was decanted, water was added, and the mixture was stirred and refluxed. Cool with vigorous stirring until the oil is completely converted to solid particles. Drying gave the compound. The obtained compound, anhydrous potassium carbonate, 2-Bromopropane and dimethylformamide were stirred at 110 ° C., and the obtained compound, triethyl orthoformate, morpholine, glacial acetic acid and dimethylformamide were reacted by heating with stirring. The obtained crude product was recrystallized with ethanol to obtain ipriflavone.

Last Update：2022-01-01 09:24:19

ipriflavone - Standard

Authoritative Data Verified Data

This product is 7-isopropoxy-3-phenyl-4h-1-benzopyran-4-one. Calculated as dried product, the content of C18H1603 shall not be less than 98.5%.

Last Update：2024-01-02 23:10:35

ipriflavone - Trait

Authoritative Data Verified Data

This product is white or off-white crystalline or crystalline powder; Odorless.
This product is soluble in N ,N-dimethylformamide or chloroform, soluble in acetone or ethyl acetate, slightly soluble in anhydrous ethanol or ether, almost insoluble in water.

melting point

The melting point of this product (General 0612) is 116~120°C.

Last Update：2022-01-01 13:36:43

ipriflavone - Use

Open Data Verified Data

developed by Nippon-Japan Pharmaceutical Industry Co., Ltd., launched in 1988. The drug for improving osteopenia caused by osteoporosis directly acts on bone, inhibits bone resorption, and increases the secretion of calcium by estrogen.

Last Update：2022-01-01 09:24:19

ipriflavone - Differential diagnosis

Authoritative Data Verified Data

take about 0.lg of this product, add 5ml of anhydrous ethanol, dissolve at a slight temperature, add 0.5ml of hydrochloric acid and 0.05g of magnesium powder, shake slightly, and place for 10 minutes. The solution shows yellow color.
take this product, add anhydrous ethanol to dissolve and dilute to prepare a solution containing about l0ug per lml, and measure by UV-Vis spectrophotometry (General rule 0401), there is a maximum absorption at the wavelength of 249nm and 298nm, and a minimum absorption at the wavelength of 277nm.
The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 616).

Last Update：2022-01-01 13:36:44

ipriflavone - Safety

Open Data Verified Data

mouse, rat LDso( mg/kg):>10 000 oral,>2500 intraperitoneal and subcutaneous.

Last Update：2022-01-01 09:24:20

ipriflavone - Exam

Authoritative Data Verified Data

acidity

take 2.0g of this product, add 100ml of water, put it in a water bath to shake and dissolve for 10 minutes, immediately let it cool, filter, take 25ml of continued filtrate, add 2 drops of phenolphthalein indicator solution, titrate to microscopic red with hydrogen sodium chloride titration solution (0.02mol/L), consume sodium hydroxide titration solution (0.02mol/L not to pass 0.10.

chloride

take 25ml of the filtrate under the above acidity item and check it according to the law (General rule 0801). Compared with the control solution made of 0.020% ml of standard sodium chloride solution, it should not be more concentrated ().

Related substances

take this product, add methanol to dissolve and dilute to make a solution containing about 0.2mg per 1 ml, as a test solution; Take appropriate amount of precision, A solution containing 2ug per 1 ml was prepared as a control solution by quantitative dilution with methanol. According to the chromatographic conditions under the content determination item, 20 u1 of the test solution and the control solution are respectively injected into the liquid chromatograph, and the chromatogram is recorded to 2 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (1.0%).

loss on drying

take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).

ignition residue

take l.Og of this product and check it according to law (General rule: 0841). The residual residue shall not exceed 0.1%.

Heavy metals

The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).

Last Update：2022-01-01 13:36:45

ipriflavone - Content determination

Authoritative Data Verified Data

measured by high performance liquid chromatography (General 0512).

chromatographic conditions and system suitability test

silica gel bonded with eighteen alkyl silane was used as a filler; Methanol-water (75:25) was used as a mobile phase; The detection wavelength was 250mn. The number of theoretical plates is not less than 2500 calculated according to the peak of ipriflavone.

assay

take an appropriate amount of this product, precisely weigh it, add methanol to dissolve and quantitatively dilute it to make a solution containing about 20ug ipriflavone per lml. Take 20u1 and inject it into human liquid chromatograph to record the chromatogram; another ipriflavone reference product was determined by the same method and calculated by peak area according to external standard method.

Last Update：2022-01-01 13:36:46

ipriflavone - Category

Authoritative Data Verified Data

calcium modulator.

Last Update：2022-01-01 13:36:46

ipriflavone - Storage

Authoritative Data Verified Data

It is protected from light and sealed in a cool place.

Last Update：2022-01-01 13:36:46

ipriflavone - Ipriflavone Tablets

Authoritative Data Verified Data

This product contains ipriflavone (C18H1603) should be labeled amount of 93.0% ~ 107.0%.

trait

This product is white or off-white.

identification

take an appropriate amount of fine powder of this product (about 0.lg of ipriflavone), add an appropriate amount of anhydrous ethanol, and shake for 10 minutes at a slight temperature to dissolve ipriflavone, let it cool and filter, the filtrate was mixed with 0.05 mL of hydrochloric acid and g of magnesium powder, slightly shaken and left for 10 minutes, showing yellow color.
in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
take an appropriate amount of the fine powder of this product, add anhydrous ethanol to slightly warm shake, dissolve ipriflavone, let it cool, dilute it with anhydrous ethanol to make a solution containing 10ug ipriflavone per 1 ml, shake well, after filtering, the filtrate was taken and the maximum absorption was measured by UV-Vis spectrophotometry (General 0401) at the wavelengths of NM and NM, and the minimum absorption was measured at the wavelength of 277mn.

examination

dissolution: according to the method for determination of dissolution and release (General rule 0931, second method), 1.0% sodium dodecyl sulfate solution was used as dissolution medium at 100 rpm, and operated according to law, after 60 minutes, take 10ml of the solution for filtration, take 5ml of the continued filtrate in a precise amount, dilute to 100ml with the dissolution medium, and use it as the test solution; Take about 10 mg of the ipriflavone reference by precise weighing, in a 1000ml measuring flask, about 600ml of dissolution medium was added, and ultrasound was carried out in a warm water bath for 20 minutes to dissolve ipriflavone, cool, dilute to the scale with the dissolution medium, and shake well to serve as a reference solution. The appropriate amount of the test solution and the reference solution was taken respectively, and the absorbance was measured at the wavelength of 303nm according to the ultraviolet-visible spectrophotometry (General rule 0401), and the dissolution amount of each tablet was calculated, the limit is 70% of the labeled amount and shall be in accordance with the provisions.
others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).

Content determination

Take 10 tablets of this product, precision weighing, fine grinding, precision weighing appropriate amount (about equivalent to ipriflavone 40mg), put in a 200ml measuring flask, add about 150ml methanol, ultrasonic 20 minutes, dissolve ipriflavone, let it cool, dilute to scale with methanol, shake well, filter, take 10ml of continued filtrate precisely, put it in a 100ml measuring flask, dilute to scale with methanol, shake well, as the test solution, 20 u1 was accurately measured and measured according to the method under the ipriflavone content measurement item.

specification

0.2g

storage

light shielding, sealed storage.

Last Update：2022-01-01 13:36:47

ipriflavone - Reference Information

biological activity	Ipriflavone (Osteofix) is a small molecule used to inhibit bone resorption.
Target	Value
use	directly acts on bone, inhibits bone resorption, and increases the secretion of calcium removal through estrogen. Used for osteoporosis and osteopenia. Hormonal drugs.
production method	method 1: anhydrous zinc chloride is dissolved in anhydrous ether, and resorcinol is added. Under stirring and ice bath cooling, dry hydrogen chloride gas is introduced to saturation. Slowly add phenylacetonitrile under vigorous stirring, then pass hydrogen chloride, and then let stand overnight. Pour off the upper ether, add 6 mol/L hydrochloric acid, and stir for a moment. After standing, pour the upper acid solution, add water, and stir and return. Cool under vigorous stirring until all the oil is converted into solid particles. Compound (I) was obtained by drying with 70% yield. Compound (I), anhydrous potassium carbonate, 2-bromopropane and dimethylformamide were stirred at 110 ℃ to obtain compound (II) with 79% yield. Compound (II), triethyl orthoformate, morpholine, glacial acetic acid and dimethylformamide are heated to boiling under stirring, reacted, and continuously steamed to produce ethanol. The obtained crude product was recrystallized with ethanol to obtain ipriflavone with 94.9% yield. Method 2: Cyclization first, then alkylation on O. Phenylacetic acid and anhydrous zinc chloride react at 130~140 ℃. Add resorcinol and react. Compound (I) was obtained with 28.4% yield. Compound (I), dimethylformamide, morpholine and triethyl orthoformate were reacted at 80~90 ℃. Compound (Ⅲ) can be obtained with 81.5% yield. Compound (Ⅲ), dimethylformamide, anhydrous potassium carbonate and 2-bromopropane were reacted at 75~95 ℃ and then raised to 100 ℃. Ipriflavone was available in 90.4% yield.

Last Update：2024-04-09 21:04:16

Shanghai Worldyang Chemical Co.,Ltd.

ipriflavone Request for Quotation

ipriflavone

CAS: 35212-22-7

Molecular Formula: C18H16O3

ipriflavone - Names and Identifiers

ipriflavone - Physico-chemical Properties

ipriflavone - Risk and Safety

ipriflavone - Nature

Open Data Verified Data

ipriflavone - Preparation Method

Open Data Verified Data

ipriflavone - Standard

Authoritative Data Verified Data

ipriflavone - Trait

Authoritative Data Verified Data

melting point

ipriflavone - Use

Open Data Verified Data

ipriflavone - Differential diagnosis

Authoritative Data Verified Data

ipriflavone - Safety

Open Data Verified Data

ipriflavone - Exam

Authoritative Data Verified Data

acidity

chloride

Related substances

loss on drying

ignition residue

Heavy metals

ipriflavone - Content determination

Authoritative Data Verified Data

chromatographic conditions and system suitability test

assay

ipriflavone - Category

Authoritative Data Verified Data

ipriflavone - Storage

Authoritative Data Verified Data

ipriflavone - Ipriflavone Tablets

Authoritative Data Verified Data

trait

identification

examination

Content determination

category

specification

storage

ipriflavone - Reference Information

Supplier List

ipriflavone