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
InChI: InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H
InChIKey: XDROKJSWHURZGO-UHFFFAOYSA-N
SMILES: C1(=O)OC2C3C=COC=3C=CC=2C=C1
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: $282
Updated: 2025/07/31

Sigma-Aldrich

Product number: A0956
Product name: Angelicin
Packaging: 25mg
Price: $619
Updated: 2025/07/31

TCI Chemical

Product number: A2573
Product name: Angelicin
Purity: >98.0%(GC)
Packaging: 25mg
Price: $370
Updated: 2025/07/31

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.

References

[1] NAZNIN A. KHATUNE . Antibacterial compounds from the seeds of Psoralea corylifolia[J]. Fitoterapia, 2004, 75 2: Pages 228-230. DOI: 10.1016/j.fitote.2003.12.018
[2] HYUN CHO1. Bakuchiol: A Hepatoprotective Compound of Psoralea corylifolia on Tacrine-Induced Cytotoxicity in Hep G2 Cells[J]. Planta medica, 2001, 67 1: 750-751. DOI: 10.1055/s-2001-18347
[3] XIANG LI. Bakuchicin induces vascular relaxation via endothelium-dependent NO-cGMP signaling.[J]. Phytotherapy Research, 2011, 25 10: 1574-1578. DOI: 10.1002/ptr.3478
[4] NAN JUN SUN. DNA Polymerase and Topoisomerase II Inhibitors from Psoralea corylifolia[J]. Journal of Natural Products , 2003, 66 5: 734. DOI: 10.1021/np030135t

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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View Lastest Price from 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran manufacturers

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

NanJing Spring & Autumn Biological Engineering CO., LTD.

Product: Angelicin Isopsoralen 523-50-2 523-50-2
Price: US $35.00/g
Min. Order: 1g
Purity: ≥98%
Supply Ability: 1000.00 kgs
Release date: 2019-07-16

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

Phytosterole Granular(Angelicin)

Angelicin[A0956]

523-50-2

BioChemical

Apoptosis and Cell Cycle

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DNA Intercalators and Crosslinkers

Inhibitors

chemical reagent

pharmaceutical intermediate

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reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

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Heterocyclic Compounds

Coumarins

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