M3501

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M3501

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8-Methoxypsoralen

≥98% (GC), powder

Synonym:8-MOP, 9-Methoxyfuro[3,2-g][1]benzopyran-7-one, Ammoidin, Methoxsalen, Xanthotoxin
CAS Number:298-81-7
Linear Formula:C12H8O4
Molecular Weight:216.19
Beilstein Registry Number:196453
EC Number:206-066-9
MDL number:MFCD00005009
PubChem Substance ID:24896845

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References

Reviews

Description

Biochem/physiol Actions8-methoxypsoralen (8-MOP) plus ultraviolet A (UVA) irradiation induces monoadducts and interstrand cross-links in DNA and therefore can be used to study DNA repair and recombination mechanisms. Cultured normal human melanocytes treated with 8-methoxypsoralen and irradiated with ultraviolet A (UVA) formed 8-methoxypsoralen-phospholipid photoadducts that could be substituted for diacylglycerol to activate protein kinase C in a cell-free system. 8-MOP is an inactivator of purified reconstituted cytochrome P450. It also inhibits substance P-induced histamine release from substance P-activated rat peritoneal mast cells by suppressing the rise in [Ca2+].
CautionProtect from light.

Properties

assay≥98% (GC)
formpowder
color white to yellow
mp148-150 °C(lit.)
solubilityH2O:  slightly soluble
 acetic acid: soluble
Gene Informationrat ... Maoa(29253)

Safety

Personal Protective Equipmentdust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard CodesXn
Risk Statements22-43
Safety Statements36/37
WGK Germany3
RTECSLV1400000

References

referenceAverbeck, D., and Averbeck, S., DNA photodamage, repair, gene induction and genotoxicity following exposures to 254 nm UV and 8-methoxypsoralen plus UVA in a eukaryotic cell system. Photochem. Photobiol. 68, 289-295, (1998) Abstract
 Dardalhon, M., et al., Mitotic recombination and localized DNA double-strand breaks are induced after 8-methoxypsoralen and UVA irradiation in Saccharomyces cerevisiae. Curr. Genet. 34, 30-42, (1998) Abstract
 Meniel, V., et al., Preferential incision of interstrand crosslinks induced by 8-methoxypsoralen plus UVA in yeast during the cell cycle. Mutat. Res. 384, 23-32, (1997) Abstract
 Anthony, F.A., Psoralen-fatty acid adducts activate melanocyte protein kinase C. . Photoimmunol. Photomed. 13, 9, (1997)
 Koenigs, L.L., and Trager, W.F., Mechanism-based inactivation of cytochrome P450 2B1 by 8-methoxypsoralen and several other furanocoumarins. Biochemistry 37, 13184-13193, (1998) Abstract
 Hickman, D., et al., Evaluation of the selectivity of in vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities. Drug Metab. Dispos. 26, 207-215, (1998) Abstract
 Amano, H., et al., Inhibition of substance-P-induced histamine release from rat peritoneal mast cells by 8-methoxypsoralen plus long-wave ultraviolet light irradiation. Int. Arch. Allergy Immunol. 115, 55-60, (1998) Abstract
MerckMerck 13,6018
BeilsteinBeil. 19,V,6,15
 Aldrich MSDS 1, 1196:C / Corp MSDS 1 (2), 2272:B / FT-IR 1 (2), 684:D / FT-IR 2 (3), 3620:A / FT-NMR 1 (3), 173:B / NMR-Reference 2 (2), 554:A / RegBook 1 (2), 2433:D / Sax 6, 2738 / Sigma FT-IR 1 (2), 716:C / Structure Index 1, 385:E:6