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ChemicalBook >> CAS DataBase List >>Ipriflavone

Ipriflavone

CAS No.
35212-22-7
Chemical Name:
Ipriflavone
Synonyms
YAMBOLAP;Ipriavone;Ipriflavon;7-ISOPROPOXYISOFLAVONE;Ipriflavone (Osteofix);7-(1-methylethoxy)-3-phenyl-4h-1-benzopyron-4-one;tc80;osten;fl113;osteofix
CBNumber:
CB0698496
Molecular Formula:
C18H16O3
Molecular Weight:
280.32
MDL Number:
MFCD00221719
MOL File:
35212-22-7.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-06-03 11:24:09
Product description Number Pack Size Price
7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one 97% 381551 5g $273
Ipriflavone analytical standard 16499 100mg $92
Ipriflavone >98.0%(GC) I0669 5g $47
Ipriflavone >98.0%(GC) I0669 25g $138
Ipriflavone ≥98% 26319 1mg $54
More product size

Ipriflavone Properties

Melting point 116-120 °C(lit.)
Boiling point 363.04°C (rough estimate)
Density 1.2170 (rough estimate)
refractive index 1.4700 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility 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)
form powder to crystal
color White to Almost white
Merck 14,5074
InChI InChI=1S/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
SMILES C1OC2=CC(OC(C)C)=CC=C2C(=O)C=1C1=CC=CC=C1
LogP 4.245 (est)
CAS DataBase Reference 35212-22-7(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 80BJ7WN25Z
ATC code M05BX01
UNSPSC Code 85151701
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
PPE Eyeshields, Gloves, type N95 (US)
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  24/25-36/37/39-27-26
WGK Germany  2
RTECS  DJ3100500
HS Code  29329990
Storage Class 11 - Combustible Solids

Ipriflavone price More Price(68)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 381551 7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one 97% 35212-22-7 5g $273 2026-04-30 Buy
Sigma-Aldrich 16499 Ipriflavone analytical standard 35212-22-7 100mg $92 2022-05-15 Buy
TCI Chemical I0669 Ipriflavone >98.0%(GC) 35212-22-7 5g $47 2026-04-30 Buy
TCI Chemical I0669 Ipriflavone >98.0%(GC) 35212-22-7 25g $138 2026-04-30 Buy
Cayman Chemical 26319 Ipriflavone ≥98% 35212-22-7 1mg $54 2026-04-30 Buy
Product number Packaging Price Buy
381551 5g $273 Buy
16499 100mg $92 Buy
I0669 5g $47 Buy
I0669 25g $138 Buy
26319 1mg $54 Buy

Ipriflavone Chemical Properties,Uses,Production

Description

Ipriflavone, 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.

Chemical Properties

white powder

Originator

Chinoin (Japan)

Uses

7-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.

Uses

anabolic

Definition

ChEBI: 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.

brand name

Osten

benefits

Ipriflavone is used clinically to treat osteoporosis. Bodybuilders also use ipriflavone, but enough experimental data supports this purpose. It has been shown to have anti-inflammatory and antioxidant activity. It helps to reduce bone loss, increase bone density, and reduce the risk of developing osteoporosis. It has also been found to help reduce neuroinflammation . In addition, it has been found to help reduce the risk of certain types of cancer, improve cognitive function and reduce the risk of depression.

General Description

7-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.

Side effects

Ipriflavone should be taken under medical supervision only. It can produce side effects such as stomach pain, diarrhoea, dizziness, etc. It may have a sudden increase in the WBC count if administered for six months or more. When the treatment with Ipriflavone is on, it is suggested that the WBC count should be monitored. 

Synthesis

7-Hydroxyisoflavone

13057-72-2

2-Bromopropane

75-26-3

Ipriflavone

35212-22-7

General procedure for the synthesis of epoxyflavone from 7-hydroxy-3-phenyl-4H-benzopyran-4-one and 2-bromopropane: To a 30 ml DMF solution of 2.50 g of 7-hydroxy-3-phenyl-4H-benzopyran-4-one (10.5 mmol) was added 1.80 g of anhydrous K2CO3 (13.0 mmol) and 3.0 ml of 2-bromopropane ( 32.0 mmol). The reaction mixture was stirred at 80 °C for 4 h. After completion of the reaction, the mixture was poured into ice water. The precipitate was collected by filtration and washed with a small amount of water and dried to give the crude product. The crude product was purified by Sephadex LH-20 column chromatography (eluent: chloroform:methanol = 7:3), and the fraction containing the target product was collected, concentrated, and recrystallized from acetone to give 1.05 g of epsilon-flavonoid crystals with a yield of 42% (w/w) and a melting point of 110-111 °C. The product structure was determined by 1H NMR. The structure of the product was confirmed by 1H NMR, 13C NMR and mass spectrometry (MS).1H NMR (DMSO-d6) δ: 1.33 (-CH3), 1.34 (-CH3), 4.86 (m, 1H, >CH2-), 7.05 (dd, 1H, J = 8.86, 2.20 Hz, 6-H), 7.16 (d, 1H, J = 2.50 Hz, 8-H), 7.38 (t, 1H, J = 6.78 Hz, 4'-H), 7.44 (t, 2H, J = 7.76, 1.6 Hz, 3',5'-H), 7.59 (d, 2H, J = 8.09, 1.6 Hz, 2',6'-H), 8.22 (d, 1H, J = 8.86 Hz, 5-H), 8.46 (s, 1H 128.1 (C-3',5'), 128.9 (C-2',6'), 132.0 (C-4'), 154.0 (C-2), 157.5 (C-9), 162.0 (C-7), 174.1 (C-4). , 279.5 (M-H)-. Elemental analysis (C18H16O3) calculated values: C, 77.12; H, 5.75. measured values: C, 76.50; H, 5.69.

in vitro

Ipriflavone inhibits the proliferation and DNA synthesis of MDA-231 cells and blocks the ligand-induced phosphorylation of Tyr(845) of the EGFR. Ipriflavone does not promote apoptosis of MDA-231 cells. Ipriflavone also promotes the deposition of calcium and the formation of mineralized nodules by newborn rat calvarial osteoblast-like cells as well as the activity of alkaline phosphatase.

in vivo

Ipriflavone ameliorated the host inflammatory response associated with activation of NLRP3 inflammasomes at the implantation site, which was characterised by inflammatory cell infiltration and reduced levels of the pro-inflammatory cytokine interleukin-1β. Daily oral administration of ipriflavone at 12 mg/mouse significantly inhibits the development of new osteolytic bone metastases and the progression of established osteolytic lesions, prolonging the life of tumor-bearing mice. Ipriflavone reduces the number of osteoclasts at the bone-cancer interface with no severe adverse effects on the host. 1-month treatment with ipriflavone increases bone density and improves the biomechanical properties of adult rat male bones without altering mineral composition.

References

[1] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # 5, p. 497 - 504
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 18, p. 4069 - 4081
[3] Patent: WO2004/2470, 2004, A1. Location in patent: Page/Page column 22-23
[4] Patent: US3949085, 1976, A

13057-72-2
75-26-3
15892-23-6
35212-22-7
Synthesis of Ipriflavone from 7-Hydroxyisoflavone and 2-Bromopropane and 2-BUTANOL
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osten tc80 osteofix Iprflavone IPRIFLAVONE(P) 7-ISOPROPOXY-3-PHENYL-4H-1-BENZOPYRAN-4-ONE 97% 7-ISOPROPOXYISOFLAVONE JP IOPAMIDOLUSP2960166-93-0 IPRIFLAVONE (7-ISOPROPOXYISOFLAVONE) IPRIFLAVONE 7-ISOPROPYLOXYISOFLAVONE 7-Isoproxyisoflavone 7-ISOPROPOXY-3-PHENYL-4H-1-BENZOPYRAN-4-ONE 7-(1-methylethoxy)-3-phenyl-4h-1-benzopyran-4-on 7-(1-methylethoxy)-3-phenyl-4h-1-benzopyran-4-one fl113 4H-1-Benzopyran-4-one, 7-(1-methylethoxy)-3-phenyl- 7-Isopropyloxy-3-phenyl-4H-1-benzopyran-4-one Ipriflavone,99% 7-isopropoxy-3-phenyl-4H-chromen-4-one 7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one, >=99% Ipriflavone (7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one) Ipriflavone SynonyMs 7-Isoproxyisoflavone Iprosten Ipriflavone> Ipriflavone RS Ipriflavone USP/EP/BP IpriflavoneQ: What is Ipriflavone Q: What is the CAS Number of Ipriflavone Q: What is the storage condition of Ipriflavone Q: What are the applications of Ipriflavone Ipriflavon 7-ISOPROPOXYISOFLAVONE Ipriflavone (Osteofix) Ipriavone 7- Isopropyl Isoflavone 3-phenyl-7-(propan-2-yloxy)-4H-chromen-4-one Ipriflavone 99%min Ipriflavone, ≥ 98.0% Yipu Flavonoids Ipriflavone, 10 mM in DMSO 7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one 7-(1-methylethoxy)-3-phenyl-4h-1-benzopyron-4-one YAMBOLAP 35212-22-7 C18H16O3 Building Blocks Heterocyclic Building Blocks Pyrans APIs FINE Chemical & INTERMEDIATES Iso-Flavones Biochemistry Flavonoids Nutraceuticals Food & Flavor Additives
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