35212-22-7

Basic information

• Product Name: Ipriflavone
• Synonyms: osten;tc80;osteofix;Iprflavone;IPRIFLAVONE(P);Ipriflavon;7-ISOPROPOXY-3-PHENYL-4H-1-BENZOPYRAN-4-ONE 97%;7-ISOPROPOXYISOFLAVONE JP
• CAS NO: 35212-22-7
• Molecular Formula: C₁₈H₁₆O₃
• Molecular Weight: 280.32
• EINECS: 201-641-0
• Product Categories: FINE Chemical & INTERMEDIATES;Iso-Flavones;APIs;Biochemistry;Flavonoids;Nutraceuticals;Food & Flavor Additives
• Mol File: 35212-22-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 116-120 °C(lit.)
• Boiling Point: 363.04°C (rough estimate)
• Flash Point: 209.3 °C
• Appearance: white crystalline powder
• Density: 1.2170 (rough estimate)
• Vapor Pressure: 8.47E-08mmHg at 25°C
• Refractive Index: 1.4700 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Merck: 14,5074
• CAS DataBase Reference: Ipriflavone(CAS DataBase Reference)
• NIST Chemistry Reference: Ipriflavone(35212-22-7)
• EPA Substance Registry System: Ipriflavone(35212-22-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26
• WGK Germany: 2
• RTECS: DJ3100500
• Hazardous Substances Data: 35212-22-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ipriflavone is used as an anabolic agent for promoting bone formation and decreasing bone loss in conditions such as osteoporosis. It enhances the activity of osteoblasts, leading to the deposition of calcium and the formation of mineralized nodules, as well as increasing the activity of alkaline phosphatase.
Used in Orthopedics:
Ipriflavone is used as a treatment for primary and secondary osteoporosis, as well as disorders of osteogenesis. It is considered a calcium metabolism regulator that appears to have minimal significant side effects, making it a suitable option for long-term use.
Used in Drug Delivery Systems:
In a study, Ipriflavone was used as a model drug to functionalize mesoporous bioactive glasses (MBG). As a hydrophobic anti-osteoporotic drug, it easily attaches to the surface of MBG, resulting in long-term drug delivery, which can be beneficial for the sustained treatment of osteoporosis.
Brand Name:
Ipriflavone is commercially available under the brand name Osten.

Originator

Chinoin (Japan)

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

Upstream product

• 75-30-9 2-iodo-propane 
• 13057-72-2 7-hydroxyisoflavone 
• 75-26-3 isopropyl bromide 
• 3669-41-8 1-(2,4-dihydroxyphenyl)-2-phenylethanone 
• 78-92-2 iso-butanol 
• 1092975-69-3 7-isopropyloxyflavanone 
• 595-90-4 tetraphenyltin(IV) 
• 38111-44-3 phenylzinc(II) bromide 

Downstream Products

• 163618-97-1 2-hydroxy-4-isopropoxybenzoic acid 
• 163618-93-7 methyl 2-hydroxy-4-isopropyl benzoate 
• 1232561-77-1 6-phenyl-7-(2-hydroxy-4-isopropoxyphenyl)-[1,2,4]triazolo[4,3-a]pyrimidine 
• 1232562-10-5 3-hydroxy-6-phenyl-7-(2-hydroxy-4-isopropoxyphenyl)-[1,2,4]triazolo[4,3-a]pyrimidine 
• 1233943-84-4 1-{4-[2-hydroxy-4-(1-methylethoxy)phenyl]-5-phenylpyrimidin-2-yl}thiourea 
• 1225387-33-6 6-phenyl-7-(2-hydroxy-4-isopropoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 1365659-25-1 3-cyano-6-phenyl-7-(2-hydroxyl-4-isopropoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 1380484-07-0 8-carbamoyl-4-(2-hydroxy-4-isopropoxyphenyl)-3-phenylimidazo[1,5-a]pyrimidine 
• 1606136-71-3 2-methyl-6-phenyl-7-(2-hydroxyl-4-isopropoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 1427272-79-4 7-isopropoxy-3-(p-tolyl)-4H-chromen-4-one 

Relevant articles and documents

Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1H-Pyrazoles derivatives

A series of 3,4-diaryl-1H-pyrazoles derivatives were designed and synthesized by the reaction of 3-heteroarylchromones and 3-phenylchromones with hydrazine hydrate in good yields. All of those compounds were characterized by 1H NMR, 13C NMR, IR, and HRMS. Moreover, 3-(2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-1H-pyrazole and 3-(2,4-dihydroxy phenyl)-4-(4-methoxyphenyl)-1H-pyrazole were further conformed by the single crystal X-ray diffraction. In addition, the antifungal activity against five phytopathogenic fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani and Fusarium solani) of 3,4-diaryl-1H-pyrazoles were evaluated. 3-(2-Hydroxy-4-isopropoxyphenyl)-4-phenyl-1H-pyrazole was more better and broader inhibitory effect on Cytospora sp., C. gloeosporioides, A. solani and Fusarium solani with IC50 values of 26.96, 28.84, 16.77 and 22.10 μg/mL, respectively. 4-(4-Fluorophenyl)-3-(2-hydroxy-4-methoxyphenyl)-1H-pyrazole exhibited fairly effective antifungal activity against Cytospora sp., C. gloeosporioides and A. solani with IC50 values of 11.91, 14.92 and 16.98 μg/mL, respectively.

Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes

Transition-metal-free LiCl-promoted cross-coupling reactions of tetraphenyltin, trichlorophenyl-, dichlorodiphenyl-, and chlorotriphenylstannanes with aryl halides in DMF provided access to biaryls in good to high yields. Up to four phenyl groups were transferred from the organostannanes substrates. The aryls bearing electron-withdrawing groups in either halides or organotin substrates gave coupling products in higher yields. The methodology has been applied for the efficient synthesis of ipriflavones.

Thallium(III) p-tosylate mediated oxidative 2,3-aryl rearrangement: A new useful route to ipriflavone and its analogs

A new route for the synthesis of ipriflavone, an antiosteoporotic agent, is described that has four steps and 60% yields starting from resacetophenone (2). The key step of the present methodology is thallium(III) p-tosylate mediated oxidative 2,3-aryl rearrangement of flavanone to generate the isoflavone ring system of ipriflavone in a highly efficient manner. Copyright Taylor & Francis Group, LLC.

COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH

The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.

Synthesis of daidzin analogues as potential agents for alcohol abuse

Daidzin, the active principle of an herbal remedy for 'alcohol addiction', has been shown to reduce alcohol consumption in all laboratory animals tested to date. Correlation studies using structural analogues of daidzin suggests that it acts by raising the monoamine oxidase (MAO)/mitochondrial aldehyde dehydrogenase (ALDH-2) activity ratio (J. Med. Chem. 2000, 43, 4169). Structure-activity relationship (SAR) studies on the 7-O-substituted analogues of daidzin have revealed structural features important for ALDH-2 and MAO inhibition (J. Med. Chem. 2001, 44, 3320). We here evaluated effects of substitutions at 2, 5, 6, 8, 3′ and 4′ positions of daidzin on its potencies for ALDH-2 and MAO inhibition. Results show that analogues with 4′-substituents that are small, polar and with hydrogen bonding capacities are most potent ALDH-2 inhibitors, whereas those that are non-polar and with electron withdrawing capacities are potent MAO inhibitors. Analogues with a 5-OH group are less potent ALDH-2 inhibitors but are more potent MAO inhibitors. All the 2-, 6-, 8- and 3′-substituted analogues tested so far do not inhibit ALDH-2 and/or have decreased potencies for MAO inhibition. This, together with the results obtained from previous studies, suggests that a potent antidipsotropic analogue would be a 4′,7-disubstituted isoflavone. The 4′-substituent should be small, polar, and with hydrogen bonding capacities such as, -OH and -NH2; whereas the 7-substituent should be a straight-chain alkyl with a terminal polar function such as -(CH 2)n-OH with 2≤n ≤6, -(CH2) n-COOH with 5≤n ≤10, or -(CH2)n-NH 2 with n ≥4.

Ipriflavone preparation process

Process for the preparation of ipriflavone consisting in the following steps: a) reaction of 2,4-dihydroxy-phenyl-benzyl-ketone of formula (II) with ethyl orthoformate in dimethylformamide as solvent and in the presence of a catalyst consisting of morpholine, to yield 7-hydroxyisoflavone of formula (III), b) separation of product (III) from the reaction residue, c) alkylation of product (III) from step b) with isopropyl halide to obtain ipriflavone, wherein: I. step a) is carried out at a temperature ranging from 115 to 120° C. using a 2,4-dihydroxy-phenyl-benzyl-ketone (II) weight/solvent volume (w/v) ratio lower than 1:4; II. step b) consists in the precipitation of the corresponding salt with dicyclohexylamine of formula (IV). The process yields 7-hydroxyisoflavone (III) in high yields within short reaction times (2 h max.) and ipriflavone with impurity ≤0.1%. STR1

Tritium Labeling of 7-Isopropoxyisoflavone

Catalytic tritiodehalogenation of 8-bromoipriflavone and 6,8-dibromoipriflavone resulted in [8-3H]ipriflavone (3) and [6,8-3H2]ipriflavone (7) with specific activities of 1.08 TBq/mmol (29.2 Ci/mmol) and 1.94 TBq/mmol (52.4 Ci/mmol), respectively. 8-Bromoipriflavone was synthesized by direct bromination of ipriflavone, while 6,8-dibromoipriflavone was formed by isopropylation of the phenolic OH group of 6,8-dibromo-7-hydroxyisoflavone which itself was prepared from 7-hydroxyisoflavone and elemental bromine.

Process for the preparation of substituted isoflavone derivative

The invention relates to a process for the preparation of pure isoflavone derivatives of the general formula (I), STR1 wherein R stands for hydrogen or isopropyl, R2 and R3 stand for hydrogen or C1-2 alkoxy by reacting a rezorcinol-derivative of the general formula (III) STR2 wherein R2 and R3 are as given above with ethyl-orthoformiate of the formula (IV) in the presence of a base and optionally by alkylating the product.

Ground mixture

A ground mixture of a poorly soluble crystalline drug and an adsorbent is remarkably improved in the rates of dissolution and adsorption of the drug.