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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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Liang Feng et al.
Archives of pharmacal research, 33(2), 225-230 (2010-03-03)
Coumarin components from Psoralea corylifolia L. are novel drugs in which psoralen and isopsoralen are the active components. The pharmacokinetics, tissue distribution and excretion of the two compounds were studied by liquid chromatography-tandem mass spectrometry after intravenous administration to Wistar
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
Paola Barraja et al.
Bioorganic & medicinal chemistry, 18(13), 4830-4843 (2010-07-16)
In the search for new photochemotherapeutic agents, a series of derivatives of the ring system pyrrolo[3,2-h]quinoline--bioisosters of the angular furocoumarin angelicin--were synthesized through a four-step synthetic approach, in reasonable overall yields. Eight of the synthesized derivatives showed a remarkable phototoxicity
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
Paola Barraja et al.
ChemMedChem, 6(7), 1238-1248 (2011-05-17)
Heteroanalogues of angelicin, pyrrolo[3,2-h]quinazolines, were synthesized with the aim of obtaining new potent photochemotherapeutic agents. Many derivatives caused a significant decrease in cell proliferation in several human tumor cell lines after irradiation with UVA light (GI(50) =15.2-0.2 μM). Their phototoxicity
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