Benzarone

ChemicalBook > CAS DataBase List > Benzarone

Product Name: Benzarone
CAS No.: 1477-19-6
Chemical Name: Benzarone
Synonyms: 2-Ethyl-3-p-hydroxybenzoylbenzofuran;Vasoc;L 2197;Venagil;Benzaron;Benzarone;NSC 82134;Benzarona;Benzaronum;Benzarone CRS
CBNumber: CB6893840
Molecular Formula: C17H14O3
Formula Weight: 266.29
MOL File: 1477-19-6.mol

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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)
pka: 7.68±0.15(Predicted)
color: Pale Yellow to Light Brown
EPA Substance Registry System: Methanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)- (1477-19-6)

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Safety

HS Code: 2932.19.1000
Toxicity: LD50 ipr-mus: 200 mg/kg AIPTAK 154,94,65

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: L129305
Product name: Benzarone
Purity: Aldrich
Packaging: 10mg
Price: $139
Updated: 2024/03/01

Sigma-Aldrich

Product number: B0490000
Product name: Benzarone
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: b0490000
Price: $153
Updated: 2024/03/01

TCI Chemical

Product number: E1289
Product name: Benzarone
Packaging: 1G
Price: $36
Updated: 2024/03/01

TCI Chemical

Product number: E1289
Product name: Benzarone
Packaging: 5G
Price: $181
Updated: 2024/03/01

TRC

Product number: B185150
Product name: Benzarone
Packaging: 25mg
Price: $65
Updated: 2021/12/16

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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

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View Lastest Price from Benzarone manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: Benzbromarone EP Impurity C 1477-19-6
Price: US $0.00/mg
Min. Order: 10mg
Purity: 0.98
Supply Ability: 10g
Release date: 2024-04-02

Wuhan Boyuan Import & Export Co., LTD

Product: Benzarone 1477-19-6
Price: US $9.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000tons
Release date: 2023-06-19

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Benzarone 1477-19-6
Price: US $0.00/KG
Min. Order: 25KG
Purity: 98%min
Supply Ability: 30tons/month
Release date: 2023-02-02

1477-19-6, BenzaroneRelated Search:

4-Methoxyphenol 2-Ethoxyethanol Ethylparaben 1-Hydroxyethylidene-1,1-diphosphonic acid Ethyl propionate Methylparaben Triclosan ISOXADIFEN-ETHYL Ethyl formate 4-Ethyl-5-fluoro-6-hydroxypyrimidine 4-Hydroxy-D-(-)-2-phenylglycine Ethyl acetate 4-Hydroxybenzoic acid Trinexapac-ethyl 4-Hydroxybenzaldehyde Ethanol Dronedarone Diethyl ether

2-Ethyl-3-p-hydroxybenzoylbenzofuran

Benzarone

2-Ethylbenzofuran-3-yl 4-hydroxyphenyl ketone

Benzaron

L 2197

Venagil

(2-ethylbenzofuran-3-yl)-(4-hydroxyphenyl)methanone

NSC 82134

(2-Ethyl-3-benzofuranyl)(4-hydroxyphenyl)methanone

Benzbromarone Impurity C

(2-Ethyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone

2-Ethyl-3-benzofuranyl-p-hydroxyphenyl ketone

Vasoc

2-ETHYL-3-(4-HYDROXYBENZOYL)BENZOFURAN

Benzarone (NSC 82134)

Benzarone CRS

(2-Ethylbenzofuran-3-yl)(4-hydroxyp

Methanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)-

Benzarone (B0490000)

Benzarona

Benzaronum

Inhibitor,URAT1,uric acid,inhibit,SLC22A12,Urate transporter 1,Benzarone,Fragivix,hURAT1

Benzbromarone Impurity 3(Benzbromarone EP Impurity C)

1477-19-6

(benzarone)

Heterocycles

Heterocyclic Compound