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M3501

Supelco

8-Methoxypsoralen

analytical standard

Synonym(s):

8-MOP, 9-Methoxyfuro[3,2-g][1]benzopyran-7-one, Ammoidin, Methoxsalen, Xanthotoxin

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About This Item

Empirical Formula (Hill Notation):
C12H8O4
CAS Number:
298-81-7
Molecular Weight:
216.19
Beilstein/REAXYS Number:
196453
EC Number:
206-066-9
MDL number:
MFCD00005009
UNSPSC Code:
41116107
PubChem Substance ID:
24896845
NACRES:
NA.24

grade

analytical standard

Quality Level

100

form

crystals
fibers
powder

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

color

white to yellow

mp

148-150 °C (lit.)

solubility

H2O: slightly soluble
acetic acid: soluble

application(s)

food and beverages

format

neat

SMILES string

COc1c2OC(=O)C=Cc2cc3ccoc13

InChI

1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3

InChI key

QXKHYNVANLEOEG-UHFFFAOYSA-N

Gene Information

rat ... Maoa(29253)

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

8-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+].

Caution

Protect from light.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Muta. 2 - 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, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7069
MKCL7290
MKCC4366
MKBT6032V
SLBC0610V

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V Meniel et al.
Mutation research, 384(1), 23-32 (1997-06-09)
Interstrand crosslink (ICL) induction by 8-methoxypsoralen plus UVA and the incision step of the repair have been investigated during the mitotic cell cycle of haploid Saccharomyces cerevisiae. Cells were synchronised by elutriation and events were examined at the level of
Lourdes Santana et al.
Journal of medicinal chemistry, 49(3), 1149-1156 (2006-02-03)
This work explores the potential of the MARCH-INSIDE methodology to seek a QSAR for MAO-A inhibitors from a heterogeneous series of compounds. A Markov model was used to quickly calculate the molecular electron delocalization, polarizability, refractivity, and n-octanol/water partition coefficients
Franz Trautinger et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 12(1), 22-28 (2012-08-04)
Photopheresis is a form of phototherapy where specialized equipment is used to isolate a leukocyte fraction from the peripheral blood which is then exposed to photoactivated 8-methoxypsoralen and reinfused into the patient. At the time of its invention the treatment
Tej Pratap Singh et al.
Experimental dermatology, 21(3), 228-230 (2012-03-03)
8-Methoxypsoralen plus UVA (PUVA) photochemotherapy is an effective treatment for many skin diseases including psoriasis. However, its exact mechanism of therapeutic action is incompletely understood. Previously, in K5.hTGFβ1 transgenic psoriatic mice, we found that PUVA induces Foxp3+ CD25+ CD4+ regulatory T cells
S Whittaker et al.
The British journal of dermatology, 167(3), 678-687 (2012-08-29)
Psoralen plus ultraviolet A (PUVA) is the standard treatment for early stages of mycosis fungoides. There have been no adequate randomized controlled trials with sufficient power comparing this modality with other therapies. To assess disease response and to compare the
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