Ipriflavone

HCID 3747
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Basic information

CAS
35212-22-7
Standard SMILES
CC(C)Oc1ccc2c(=O)c(-c3ccccc3)coc2c1
InChIKey
SFBODOKJTYAUCM-UHFFFAOYSA-N
Molecular formula
C18H16O3
Average molar mass
280.3 g/mol
Monoisotopic mass
280.10994437

Names & identifiers

Preferred name
Ipriflavone
IUPAC
3-phenyl-7-propan-2-yloxychromen-4-one
English name
Ipriflavone
Molecular formula
C18H16O3
Molecular weight
280.32

Names & synonyms

ipriflavone35212-22-7OstenYambolap7-IsopropoxyisoflavoneIpriflavonaIpriflavonumOstivoneDTXSID50406797-(1-Methylethoxy)-3-phenyl-4H-1-benzopyran-4-one3-phenyl-7-(propan-2-yloxy)-4H-chromen-4-one80BJ7WN25Z
Show more names
IpriavoneIpriflavonIpriflavone (Osteofix)7-(1-methylethoxy)-3-phenyl-4h-1-benzopyron-4-onetc80fl113
NSC-755888DTXCID3020679CHEBI:31719RefChem:923535M05BX017-(1-Methylethyl)oxy-3-phenyl-4H-chromen-4-oneOsteofix7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one

Database identifiers

CAS
35212-22-7
PubChem CID
3747
DTXSID
DTXSID5040679
ChEMBL
CHEMBL165790
ChEBI
CHEBI:31719
UNII
80BJ7WN25Z
EC Number
609-092-2
Nikkaji
J19.468I

Properties

Computed structural properties

XLogP
4
Topological polar surface area
35.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
21

Experimental & physicochemical properties

Melting Point115 - 117 °C
Physical DescriptionSolid
Collision Cross Section · 2 items

161.54 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；175.72 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；155.27 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

164.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
116 · 116-120 °C(lit.)
Boiling point
363.04 °C · 363.04°C (rough estimate)
Density
1.217 · 1.2170 (rough estimate)
refractive index
1.47 · 1.4700 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
20 · DMF:20.0(Max Conc. mg/mL);71.35(Max Conc. mM)DMF:PBS (pH 7.2) (1:4):0.2(Max Conc. mg/mL);0.71(Max Conc. mM)DMSO:33.11(Max Conc. mg/mL);118.11(Max Conc. mM)Ethanol:1.5(Max Conc. mg/mL);5.35(Max Conc. mM)

Safety & regulation

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
rtecs
DJ3100500
hs_code
29329990
risk_code
36/37/38
Signal word
Warning

Chemistry & industry

Pharmacology

ATC Code · 2 items

M - Musculo-skeletal system；M05 - Drugs for treatment of bone diseases；M05B - Drugs affecting bone structure and mineralization；M05BX - Other drugs affecting bone structure and mineralization；M05BX01 - Ipriflavone

QM - Musculo-skeletal system；QM05 - Drugs for treatment of bone diseases；QM05B - Drugs affecting bone structure and mineralization；QM05BX - Other drugs affecting bone structure and mineralization；QM05BX01 - Ipriflavone

Metabolism/MetabolitesIpriflavone has known human metabolites that include 4H-1-Benzopyran-4-one, 3-(4-hydroxyphenyl)-7-(1-methylethoxy)-, 7-Hydroxyisoflavone, and 3-Phenyl-7-(1-methyl-2-hydroxyethoxy)-4H-1-benzopyran-4-one.
Cellular LocationsMembrane
Applications · 4 items

DescriptionIpriflavone, a derivative of isoflavone, is a calcium metabolism regulator useful in the treatment of primary and secondary osteoporosis, as well as disorders of osteogenesis. It appears to be without significant side-effects.

Uses7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one (Ipriflavone) has been used as a model drug in a study to functionalize the mesoporous bioactive glasses (MBG). Study suggested that since ipriflavone is a hydrophobic anti-osteoporotic drug, it easily attaches to the surface of MBG and results in long-term drug delivery.

Usesanabolic

General Description7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one (Ipriflavone), a synthetic flavonoid, is reported to stimulate the activity of osteoblasts. It is reported to promote the deposition of calcium and the formation of mineralized nodules by newborn rat calvarial osteoblast-like (ROB) cells as well as the activity of alkaline phosphatase. Ipriflavone, an isoflavone derivative, is a new drug used to decrease bone loss in osteoporosis.

Upstream & downstream products

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Ipriflavone is a member of the class of isoflavones that is isoflavone in which the hydrogen at position 7 is replaced by an isopropoxy group. A synthetic isoflavone, it was formerly used for the treatment of osteoporosis, although a randomised controlled study failed to show any benefit. It is still used to prevent osteoporosis in post-menopausal women. It has a role as a bone density conservation agent. It is a member of isoflavones and an aromatic ether.

Related reactions

10 records
New reaction record

Compound notes

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