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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:
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

Signal Word

Warning

Hazard Statements

H302,H317,H341,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Muta. 2 - Skin Sens. 1

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

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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
D Hickman et al.
Drug metabolism and disposition: the biological fate of chemicals, 26(3), 207-215 (1998-04-04)
There is a need for methodology to predict clinically significant drug-drug interactions so that clinical studies can be directed toward interactions which are likely to be clinically relevant. To this end, we evaluated selective assays for the seven drug-metabolizing cytochrome
Katarzyna Borowska et al.
International journal of pharmaceutics, 426(1-2), 280-283 (2012-02-09)
In the present study we have assessed the ability of (PAMAM) dendrimers G3 and G4 to facilitate transdermal delivery of 8-methoxypsoralen (8-MOP) in vivo. In vitro study using Franz diffusion cell revealed an enhanced transdermal flux for 8-MOP in complex
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
Y Tokura
Journal of dermatological science, 19(2), 114-122 (1999-03-31)
Modulatory effects on cytokine expression of 8-MOP in conjunction with UVA have been investigated in different systems using different cell types, including keratinocytes, lymphocytes, monocytes and endothelial cells. The vast majority of data have exhibited reduced production of cytokines in
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