Synthesis Toxicity
ChemicalBook > CAS DataBase List > 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran

2-Oxo-(2H)-furo(2,3-h)-1-benzopyran

Synthesis Toxicity
Product Name
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran
CAS No.
523-50-2
Chemical Name
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran
Synonyms
angecin;ANGELICIN;ANGELICINE;NSC 404563;isopsoralin;ISOPSORALEN;ISOPSORALENE;ISOBERGAPTEN;ANGELICIN(P);Angelicin>
CBNumber
CB9249112
Molecular Formula
C11H6O3
Formula Weight
186.16
MOL File
523-50-2.mol
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2-Oxo-(2H)-furo(2,3-h)-1-benzopyran Property

Melting point:
132-134°C
Boiling point:
104°C/4mmHg(lit.)
Density 
1.2477 (rough estimate)
refractive index 
1.6310 (estimate)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form 
Solid
color 
White
λmax
302nm(EtOH)(lit.)
BRN 
153970
LogP
2.080
CAS DataBase Reference
523-50-2(CAS DataBase Reference)
IARC
3 (Vol. 40, Sup 7) 1987
NIST Chemistry Reference
2H-furo[2,3-h]-1-benzopyran-2-one(523-50-2)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
20/21/22-36/37/38-40
Safety Statements 
26-36/37/39-37/39-36
WGK Germany 
3
RTECS 
LV0940000
HS Code 
29322090
Hazardous Substances Data
523-50-2(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A0956
Product name
Angelicin
Packaging
10mg
Price
$159.6
Updated
2024/03/01
Sigma-Aldrich
Product number
A0956
Product name
Angelicin
Packaging
25mg
Price
$349.8
Updated
2024/03/01
TCI Chemical
Product number
A2573
Product name
Angelicin
Purity
>98.0%(GC)
Packaging
25mg
Price
$411
Updated
2024/03/01
Cayman Chemical
Product number
11683
Product name
Angelicin
Purity
≥98%
Packaging
5mg
Price
$98
Updated
2024/03/01
Cayman Chemical
Product number
11683
Product name
Angelicin
Purity
≥98%
Packaging
10mg
Price
$157
Updated
2024/03/01
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2-Oxo-(2H)-furo(2,3-h)-1-benzopyran Chemical Properties,Usage,Production

Synthesis

Iodination of commercially available umbelliferone (7-hydroxycoumarin) yields 7-hydroxy-8-iodocoumarin. Acetoxy group can be introduced into hydroxyl of 7-hydroxy-8-iodocoumarin, which is used to create vaginol or vaginidiol with an isopropyl Grignard reagent and commercially available epoxy aldehydes. Subsequent acid-catalysed fragmentation of vaginol with dichloromethane in trifluoroacetic acid yields angelicin.

Toxicity

The LD50 of angelicin is 322 mg/kg which shows acute toxicity if orally administered to rats. The possible consequences are alteration in circadian rhythm and righting reflex, ataxia and analgesia.

Description

Angelicin is a furanocoumarin typically isolated from the seeds of P. corylifolia. Like other furanocoumarins, angelicin has antibacterial activities against a number of Gram (+) and Gram (-) bacteria. It has also been shown to prevent tacrine-induced cytotoxicity in human liver-derived HepG2 cells (EC50 = 47 μg/ml) and vascular relaxation in phenylephrine-precontracted rat aorta. Angelicin also weakly inhibits topoisomerase II (IC50 = 404 μM).

Chemical Properties

White Solid

Uses

Antifungal

Definition

ChEBI: Angelicin is a furanocoumarin.

Synthesis Reference(s)

Tetrahedron, 51, p. 3087, 1995 DOI: 10.1016/0040-4020(95)00070-O

Clinical Use

Angelicin derivatives are used to treat psoriasis and cancer. One way of treating these diseases is by photochemotherapy (PUVA) which combines UV irradiation with photosensitizing chemical. Also, it was shown that it is actively inhibits the synthesis of nucleic acids in tumor cells thereby decreasing their growth.

2-Oxo-(2H)-furo(2,3-h)-1-benzopyran Preparation Products And Raw materials

Raw materials

Xylene Sodium hydride Potassium hydroxide Ethyl formate Sodium chloride Ethyl (triphenylphosphoranylidene)acetate 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Potassium hydride Chloroacetaldehyde Tetrahydrofuran Diethyl ether Benzene Ethyl acetate Hydrochloric acid Sodium bicarbonate Methanol 1,3-Cyclohexanedione Magnesium sulfate PETROLEUM ETHER

Preparation Products

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2-Oxo-(2H)-furo(2,3-h)-1-benzopyran Suppliers

Americas 1 Canada 2 China 250 Europe 1 France 1 Germany 2 India 6 Japan 1 Switzerland 1 United Kingdom 9 United States 29 Global 303
SIGMA-RBI
Tel
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Fax
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Country
Switzerland
ProdList
6896
Advantage
91
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View Lastest Price from 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran manufacturers

Chongqing Zhihe Biopharmaceutical Co., Ltd.
Product
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran 523-50-2
Price
US $0.00-0.00/kg
Min. Order
0.10000000149011612kg
Purity
≥98%
Supply Ability
20tons
Release date
2024-01-04
R&D Scientific Inc.
Product
Angelicin 523-50-2
Price
US $1050.00/g
Min. Order
1g
Purity
98
Supply Ability
500 Kg
Release date
2024-03-31
Shanghai Standard Technology Co., Ltd.
Product
Isopsoralen 523-50-2
Price
US $0.00/mg
Min. Order
5mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2019-10-24

523-50-2, 2-Oxo-(2H)-furo(2,3-h)-1-benzopyranRelated Search:

Isobavachin Isopsoralenoside Isobavachromene endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate Ipratropium bromide 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran STIGMASTEROL ACETATE Psoralen pimpinellin ISOBERGAPTOL LANATIN ISOBERGAPTEN,ISOBERGAPTEN WITH HPLC ISOBERGAPTEN(SH) 4-Methylangelicin 5-methylangelicin 4,5'-dimethylangelicin STIGMASTERYL ACETATE 4,4'-dimethylangelicin

  • ANGELICIN
  • ANGELICINE
  • ISOBERGAPTEN
  • ISOPSORALEN
  • ISOPSORALENE
  • 2-OXO-[2H]-FURO[2,3-H]-1-BENZOPYRAN
  • furo(5’,4’,7,8)coumarin
  • furo(5’,4’:7,8)coumarin
  • isopsoralin
  • Isopsoralen （Angelicin）
  • FURO(2,3-H)BENZOPYRAN-2-ONE
  • ANGELICINE hplc
  • PHYTOSTEROLE GRANULAR
  • Angelicin【coumarin derivative】
  • ANGELICIN (BAKUCHICIN)(RG)
  • ANGELICIN (BAKUCHICIN)(SH)
  • ANGELICIN(P)
  • isopsoralen 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran
  • Angelicin Isopsoralen 523-50-2
  • 2-furo[2,3-h][1]benzopyranone
  • NSC 404563
  • 2H-Furo[2,3-h]chromen-2-one
  • Angelicin, froM Psoralea corylifolia L.
  • Angelicin, 98%, from Psoralea corylifolia L.
  • 2h-furo(2,3-h)(1)benzopyran-2-one
  • 2h-furo(2,3-h)-1-benzopyran-2-one
  • 3-(4-hydroxy-5-benzofuranyl)-2-propenoicacidelta-lactone
  • 3-(4-hydroxy-5-benzofuranyl)-2-propenoicacidgamma-lactone
  • 4-hydroxy-5-benzofuranacrylicacidgamma-lactone
  • angecin
  • angelicin(coumarinderiv)
  • furo(2,3-h)coumarin
  • Angelicin&gt
  • Angelicin-RM
  • 523-50-2
  • BioChemical
  • Apoptosis and Cell Cycle
  • Cell Signaling and Neuroscience
  • Cell Biology
  • DNA metabolism
  • DNA Intercalators and Crosslinkers
  • Inhibitors
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Heterocycles
  • Heterocyclic Compounds
  • Coumarins
  • Miscellaneous Natural Products