Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
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
View All Related Papers

Articles

DNA Damage and Repair

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service