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A0956

Sigma-Aldrich

Angelicin

Synonym(s):

2-Oxo-(2H)-furo(2,3-h)-1-benzopyran, 2H-Furo[2,3-h]-1-benzopyran-2-one, Isopsoralen, NSC 404563

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About This Item

Empirical Formula (Hill Notation):
C11H6O3
CAS Number:
523-50-2
Molecular Weight:
186.16
Beilstein:
153970
MDL number:
MFCD00064930
UNSPSC Code:
85151701
PubChem Substance ID:
24890472
NACRES:
NA.25

form

powder

Quality Level

200

storage temp.

2-8°C

SMILES string

O=C1Oc2c(C=C1)ccc3occc23

InChI

1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H

InChI key

XDROKJSWHURZGO-UHFFFAOYSA-N

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Application

Angelicin, an angular furocoumarin, may be used as a photoactivatable molecule that reacts with DNA and unsaturated fatty acids to form monoadducts. Angelicin may be studied as a potential phototherapeutic and to understand its mechanisms of action and effects on RNA and DNA synthesis.

Biochem/physiol Actions

Angular furocoumarin with diverse photobiological effects. Upon long-wavelength UV irradiation, forms monoadduct with double-stranded DNA and reacts with unsaturated fatty acids. Inhibits DNA and RNA synthesis and cell replication in Ehrlich ascites tumor cells.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Fang Liu et al.
The Journal of surgical research, 185(1), 300-309 (2013-07-03)
Angelicin is a furocoumarin found in Psoralea corylifolia L. fruit. The purpose of this study was to investigate the protective ability of angelicin against inflammation in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and LPS-induced in vivo acute lung injury model. The
Jiann-Yih Yeh et al.
Journal of medicinal chemistry, 53(4), 1519-1533 (2010-01-23)
By using a cell-based high throughput screening campaign, a novel angelicin derivative 6a was identified to inhibit influenza A (H1N1) virus induced cytopathic effect in Madin-Darby canine kidney cell culture in low micromolar range. Detailed structure-activity relationship studies of 6a
D Xin et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 17(2), 126-131 (2009-07-07)
The seed of Psoralea corylifolia L. (PCL), a well-known traditional Chinese medicine, has been applied as a tonic or an aphrodisiac agent and commonly used as a remedy for bone fracture, osteomalacia and osteoporosis in China. In our study, the
Marco Leonti et al.
Journal of natural medicines, 64(3), 354-357 (2010-03-20)
A new prenylated pterocarpan, named morisianine, was isolated together with the known secondary metabolites erybraedin C, psoralen and angelicin from the seeds of Bituminaria morisiana. The structures of the compounds were elucidated mainly by 1D and 2D NMR experiments as
Tsugio Kitamura et al.
The Journal of organic chemistry, 77(6), 2978-2982 (2012-03-01)
Intramolecular hydroarylation of 4-benzofuranyl alkynoates using Pd(OAc)(2) as catalyst took place selectively and efficiently, giving angular furocoumarin derivatives in high yields. The parent angelicin was obtained in 80% yield by this method. The starting 4-benzofuranyl alkynoates were easily accessible from
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