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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Li-Qun Ouyang et al.
Analytica chimica acta, 650(2), 160-166 (2009-09-02)
A method using high performance liquid chromatography with photodiode-array detection (HPLC-DAD) coupled with alternating trilinear decomposition (ATLD) algorithm was proposed for simultaneous determination of psoralen and isopsoralen in plasma and Chinese medicine "Xian Ling Gu Bao" capsule (XLGBC). In this
Yang Ye et al.
Organic letters, 14(8), 2114-2117 (2012-04-07)
The oxidative dearomatization of 3-(3-alkynyl-4-hydroxyphenyl)propanoic acid is combined with a cascade transition-metal catalyzed cyclization/addition/aromatization/lactamization sequence, which provides a novel approach to prepare furoquinolinone and angelicin derivatives in a convergent and efficient manner.
Giampietro Viola et al.
Annals of the New York Academy of Sciences, 1171, 334-344 (2009-09-03)
In this review we summarize the structure and biological effects of linear and angular psoralens. These compounds exhibit interesting biological effects on the cell cycle, apoptosis and differentiation. These molecules should be considered promising drugs in the therapy of several
Md Ataur Rahman et al.
Molecular and cellular biochemistry, 369(1-2), 95-104 (2012-07-07)
Angelicin is structurally related to psoralens, a well-known chemical class of photosensitizers used for its antiproliferative activity in treatment of different skin diseases. To verify the activity of angelicin, we employed human SH-SY5Y neuroblastoma cells to investigate its cytotoxicity, although
Yuan Gu et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(27), 3137-3143 (2009-08-13)
A rapid, specific and sensitive ultra-performance liquid chromatography/tandem mass spectrometry (UPLC/MS/MS) method has been established for simultaneous quantitation of psoralen and isopsoralen in rat plasma. Plasma samples were pretreated by direct protein precipitation with acetonitrile. Chromatographic separations were performed on
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