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

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)

Safety Information

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)

MSDS

• Language:English Provider:SigmaAldrich

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

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(523-50-2)Related Product Information

• 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