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Benzarone

Benzarone Structure
Benzarone
  • CAS No.1477-19-6
  • Chemical Name:Benzarone
  • CBNumber:CB6893840
  • Molecular Formula:C17H14O3
  • Formula Weight:266.29
  • MOL File:1477-19-6.mol
Benzarone Property
  • Melting point 124.3°
  • Boiling point 369.5°C (rough estimate)
  • Density 1.1601 (rough estimate)
  • refractive index 1.5490 (estimate)
  • storage temp. 2-8°C
  • solubility DMSO (Slightly), Methanol (Slightly)
  • form Solid
  • pka 7.68±0.15(Predicted)
  • color Pale Yellow to Light Brown
  • FDA UNII 23ZW4BG89C
  • EPA Substance Registry System Methanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)- (1477-19-6)
  • UNSPSC Code 41116107
  • NACRES NA.24
Safety
  • HS Code  :2932.19.1000
  • Toxicity :LD50 ipr-mus: 200 mg/kg AIPTAK 154,94,65
  • NFPA 704:
    0
    1 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H361
  • Precautionary statements P501-P202-P201-P280-P308+P313-P405
Benzarone Price More Price(2)
  • Brand: TCI Chemicals (India)
  • Product number: E1289
  • Product name : Benzarone
  • Purity: min. 98.0 %
  • Packaging: 1G
  • Price: ₹4500
  • Updated: 2022/05/26
  • Buy: Buy
  • Brand: TCI Chemicals (India)
  • Product number: E1289
  • Product name : Benzarone
  • Purity: min. 98.0 %
  • Packaging: 5G
  • Price: ₹8000
  • Updated: 2022/05/26
  • Buy: Buy

Benzarone Chemical Properties,Usage,Production

  • Chemical Properties Pale Yellow Solid
  • Originator Fragivix,Labaz
  • Uses Benzarone is an EYA (Eyes Absents), multifunctional protein involved in organogenesis, inhibitor which makes it a potent anticancer agent. EYA’s are over expressed in ovarian and breast cancers. As well it is involved in the synthesis of Human Uric Acid Transporter 1 inhibitors which may be used to treat kidney diseases.
  • Definition ChEBI: Benzarone is a member of 1-benzofurans.
  • Manufacturing Process The process of preparation of the 2-ethyl-3-(4'-hydroxybenzoyl)benzofurane includes the next steps: 1. To 1 mol of potassium hydroxide in absolute ethanol is added 1 mole of salicylic aldehyde. The mixture is brought to boiling point in water bath until the potassium salt formed is dissolved. One mole of coloroacetone is gradually added and the solution boiled in a reflux condenser for 2 hours. On cooling the potassium chloride precipitate is separated off by filtration. The residue is distilled to give 2-acetyl-1-benzofurane, BP: 135°C/15 mm Hg.
    2. It was reduced by hydrazine hydrate in an alkaline medium (by process of Hyuang-Minlon, J.A.C.S., 1946, 68, 2487) to give 2-ethyl-1-benzofurane BP: 211°-212°C.
    3. 2-Ethyl-1-benzofurane is condensed with 2-metoxybenzoyl chloride in the presence of tin tetrachloride (according to the process described by Bisagni, J.C.S., 1955, 3694). Thus 2-ethyl-3-(4-methoxybenzoyl)-1-benzofyrane is obtained. BP: 226°C/15 mm Hg.
    4. 1 part of 2-ethyl-3-(4-methoxybenzoyl)-1-benzofyrane is mixed with 2 parts of pyridine hydrochloride and heated at an oil bath at 210°C in N2 current for 1 hour. On cooling 10 parts of 0.5 N HCl are added. A water layer is mixed with 20 parts of 1% NaOH. The alkaline layer is separated, acidified with diluted HCl. The dropped precipitate (2-ethyl-3-(4'-hydroxybenzoyl) benzofurane) is recrystallized from acetic acid. MP: 124.3°C.
  • brand name Benzarin;Fragivix (r) forte;Vasco.
  • Therapeutic Function Antihemorrhagic
  • World Health Organization (WHO) Benzarone is given by mouth and applied topically for treatment of various vascular peripheral disorders.The decision to suspend the marketing authorization results from several reports of toxic hepatitis, including one fatal case from within Germany. The product remains registered in Italy and France.
  • Biological Activity Benzarone is an active metabolite of the urate anion transporter 1 (URAT1) inhibitor benzbromarone. It inhibits URAT1 in Xenopus oocytes expressing the human enzyme (IC50 = 2.8 μM). Benzarone also inhibits the tyrosine phosphatase activity of eyes absent homolog 3 (EYA3; IC50 = 17.5 μM), as well as reduces the proliferation and migration of human umbilical vein endothelial cells (HUVECs) when used at a concentration of 7.5 μM. It uncouples oxidative phosphorylation in isolated rat liver mitochondria and induces apoptosis and necrosis in isolated rat hepatocytes. Benzarone (25 μg/g) reduces tumor growth in an A-673 Ewing sarcoma mouse xenograft model.
  • Safety Profile Poison by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. A flammable liquid. When heated to decomposition it emits acrid and irritating smoke and fumes. See also KETONES.
  • References [1] W. STüBER H. M. Determination of benzbromarone, bromobenzarone and benzarone in plasma by gas chromatography—mass spectrometry[J]. Journal of Chromatography B: Biomedical Sciences and Applications, 1981, 224 2: Pages 327-331. DOI:10.1016/S0378-4347(00)80171-1.
    [2] PRISKA KAUFMANN. Mechanisms of benzarone and benzbromarone-induced hepatic toxicity?[J]. Hepatology, 2005, 41 4: 925-935. DOI:10.1002/hep.20634.
    [3] RAM NARESH PANDEY. Structure-activity relationships of benzbromarone metabolites and derivatives as EYA inhibitory anti-angiogenic agents.[J]. PLoS ONE, 2013: e84582. DOI:10.1371/journal.pone.0084582.
    [4] MICHAEL F. WEMPE*. Developing Potent Human Uric Acid Transporter 1 (hURAT1) Inhibitors[J]. Journal of Medicinal Chemistry, 2011, 54 8: 2701-2713. DOI:10.1021/jm1015022.
Benzarone Preparation Products And Raw materials
Raw materials
Preparation Products
Benzarone Suppliers
Global(147)Suppliers
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Benzarone Spectrum
1477-19-6, BenzaroneRelated Search:
  • Heterocyclic Compound
  • Heterocycles
  • (benzarone)
  • 苯扎隆
  • 化工试剂
  • 杂质对照品
  • 分子砌块
  • 抑制剂
  • 医用原料
  • 医药原料
  • 原料药
  • 杂环化合物
  • 医药原料药
  • 苯扎隆,10 MM DMSO 溶液
  • 苯溴马隆杂质3(苯溴马隆EP杂质C)
  • (2-乙基苯并呋喃-3-基)(4-羟基苯基)甲酮
  • 苯扎隆/苯萨容
  • 苯溴马隆EP杂质C
  • 苯扎隆 EP标准品
  • 苯溴马隆杂质C(EP)
  • 苯溴马隆杂质C
  • 苯扎隆
  • 苯萨容
  • 2-乙基-3-(4-羟基苯甲酰基)苯并呋喃
  • 2-乙基-3-对羟基苯甲酰基苯并呋喃
  • 1477-19-6
  • Benzarone, 10 mM in DMSO
  • (2-Ethylbenzofuran-3-yl)(4-hydroxyphenyl)methanone (Benzarone)
  • Benzbromarone Impurity 3(Benzbromarone EP Impurity C)
  • Inhibitor,URAT1,uric acid,inhibit,SLC22A12,Urate transporter 1,Benzarone,Fragivix,hURAT1
  • Benzaronum
  • Benzarona
  • 2-Ethyl-3-p-hydroxybenzoylbenzofuran
  • Benzarone (B0490000)
  • Methanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)-
  • (2-Ethylbenzofuran-3-yl)(4-hydroxyp
  • Benzarone CRS
  • Benzarone (NSC 82134)
  • Benzbromarone Impurity C
  • (2-Ethyl-3-benzofuranyl)(4-hydroxyphenyl)methanone
  • 2-ETHYL-3-(4-HYDROXYBENZOYL)BENZOFURAN
  • Vasoc
  • 2-Ethyl-3-benzofuranyl-p-hydroxyphenyl ketone
  • (2-Ethyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone
  • NSC 82134
  • (2-ethylbenzofuran-3-yl)-(4-hydroxyphenyl)methanone
  • Venagil
  • L 2197
  • Benzaron
  • 2-Ethylbenzofuran-3-yl 4-hydroxyphenyl ketone
  • Benzarone

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