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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
Molecular Weight:
186.16
MDL Number:
MFCD00064930
MOL File:
523-50-2.mol
MSDS File:
SDS
Last updated:2024-01-04 11:05:11

2-Oxo-(2H)-furo(2,3-h)-1-benzopyran 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)
color White
λmax 302nm(EtOH)(lit.)
BRN 153970
LogP 2.080
CAS DataBase Reference 523-50-2(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII CZZ080D7BD
NIST Chemistry Reference 2H-furo[2,3-h]-1-benzopyran-2-one(523-50-2)
IARC 3 (Vol. 40, Sup 7) 1987

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P301+P312+P330-P302+P352-P305+P351+P338
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
NFPA 704
0
3 0

2-Oxo-(2H)-furo(2,3-h)-1-benzopyran price More Price(44)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A0956 Angelicin 523-50-2 10mg $159.6 2024-03-01 Buy
Sigma-Aldrich A0956 Angelicin 523-50-2 25mg $349.8 2024-03-01 Buy
TCI Chemical A2573 Angelicin >98.0%(GC) 523-50-2 25mg $411 2024-03-01 Buy
Cayman Chemical 11683 Angelicin ≥98% 523-50-2 5mg $98 2024-03-01 Buy
Cayman Chemical 11683 Angelicin ≥98% 523-50-2 10mg $157 2024-03-01 Buy
Product number Packaging Price Buy
A0956 10mg $159.6 Buy
A0956 25mg $349.8 Buy
A2573 25mg $411 Buy
11683 5mg $98 Buy
11683 10mg $157 Buy

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

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

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran pictures 2024-03-08 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran
523-50-2
US $0.00-0.00 / kg 0.10000000149011612kg ≥98% 20tons Chongqing Zhihe Biopharmaceutical Co., Ltd.
Isopsoralen pictures 2023-02-24 Isopsoralen
523-50-2
US $0.00 / mg 5mg ≥98%(HPLC) 10 g Shanghai Standard Technology Co., Ltd.
Angelicin pictures 2023-02-13 Angelicin
523-50-2
US $120.00 / kg 1kg 99% 80MT Hebei baicao biology science and technology co., ltd
  • Isopsoralen pictures
  • Isopsoralen
    523-50-2
  • US $0.00 / mg
  • ≥98%(HPLC)
  • Shanghai Standard Technology Co., Ltd.
  • Angelicin pictures
  • Angelicin
    523-50-2
  • US $120.00 / kg
  • 99%
  • Hebei baicao biology science and technology co., ltd
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 NSC 404563 2H-Furo[2,3-h]chromen-2-one Angelicin, 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 Isopsoralen 523-50-2 2-furo[2,3-h][1]benzopyranone Angelicin, 98%, from Psoralea corylifolia L. Angelicin> 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