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P8399

Sigma-Aldrich

Psoralen

≥99% (HPLC)

Synonym(s):

6,7-Furanocoumarin, 7H-Furo[3,2-g]benzopyran-7-one, Ficusin, Furo[3,2-g]coumarin

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About This Item

Empirical Formula (Hill Notation):
C11H6O3
CAS Number:
66-97-7
Molecular Weight:
186.16
Beilstein/REAXYS Number:
152784
EC Number:
200-639-7
MDL number:
MFCD00010520
UNSPSC Code:
12352200
PubChem Substance ID:
24898918
NACRES:
NA.77

Quality Level

200

assay

≥99% (HPLC)

form

powder

fluorescence

λex 335 nm; λem 460 nm (pH 7.0)

storage temp.

2-8°C

SMILES string

O=C1Oc2cc3occc3cc2C=C1

InChI

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

InChI key

ZCCUUQDIBDJBTK-UHFFFAOYSA-N

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Application

Psoralen has been used:
  • as a crosslinker for dsRNA for in- situ hybridization studies
  • in testing melanin dispersal effects in fish scale melanophores
  • to test its stimulatory effects in osteoblast a cell proliferation assay
  • as a reference standard in high-performance liquid chromatography (HPLC)

Photochemical reagent for the investigation of nucleic acid structure and function.

Biochem/physiol Actions

Psoralen belongs to the linear type furanocoumarins. It intercalates and induces interstrand cross-links in DNA. On UV exposure psoralen is excited leading to irreversible intercalation with DNA by covalent bond formation. This property of psoralen ultraviolet A light (PUVA) is exploited in treating skin diseases and cutaneous T-cell lymphoma. However, usage psoralen also leads to hepatotoxicity and cytotoxicity by the generation of psoralen photoproducts (POPs). It may be useful in treating osteoporosis

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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’.

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In vitro responses of fish melanophores to lyophilized extracts of Psoralea corylifolia seeds and pure psoralen
Ali SA, et al.
Pharmaceutical biology, 49(4), 422-427 (2011)
Psoralen induced liver injury by attenuating liver regenerative capability
Zhou W, et al.
Frontiers in Pharmacology, 9, 1179-1179 (2018)
The mitochondrial effects of novel apoptogenic molecules generated by psoralen photolysis as a crucial mechanism in PUVA therapy
Caffieri S, et al.
Blood, 109(11), 4988-4994 (2007)
Psoralen and ultraviolet a light treatment directly affects phosphatidylinositol 3-kinase signal transduction by altering plasma membrane packing
Van Aelst B, et al.
The Journal of Biological Chemistry, 291(47), 24364-24376 (2016)
Psoralen stimulates osteoblast proliferation through the activation of nuclear factor-kappaB-mitogen-activated protein kinase signaling
Li F, et al.
Experimental and Therapeutic Medicine, 14(3), 2385-2391 (2017)
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