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Sigma-Aldrich

5-Methoxypsoralen

99%

Synonym(s):

4-Methoxyfuro[3,2-g]benzopyrane-7-one, Bergapten, Geralen, Heraclin, Majudin

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About This Item

Empirical Formula (Hill Notation):
C12H8O4
CAS Number:
484-20-8
Molecular Weight:
216.19
Beilstein/REAXYS Number:
19560
EC Number:
207-604-5
MDL number:
MFCD00010272
UNSPSC Code:
12352103
PubChem Substance ID:
24856667
NACRES:
NA.23

assay

99%

mp

190-193 °C (lit.)

SMILES string

COc1c2C=CC(=O)Oc2cc3occc13

InChI

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

InChI key

BGEBZHIAGXMEMV-UHFFFAOYSA-N

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Application

5-Methoxypsoralen has been studied for its use in oral photochemotherapy in the treatment of psoriasis and other skin diseases.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

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

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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M T Conconi et al.
Pharmacology & toxicology, 82(4), 193-198 (1998-05-19)
The in vitro antiproliferative activity and in vivo phototoxicity of some methyl derivatives of 5-methoxypsoralen and 5-methoxyangelicin, i.e. 4,4'-dimethyl-5-methoxyangelicin (compound I), 3,4'-dimethyl-5-methoxyangelicin (compound II), 4,4'-dimethyl-5-methoxypsoralen (compound III); and 3,4'-dimethyl-5-methoxypsoralen (compound IV), have been investigated. The effects of the compounds were
Silke B Bodendiek et al.
European journal of medicinal chemistry, 44(5), 1838-1852 (2008-12-06)
The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we
W McNeely et al.
Drugs, 56(4), 667-690 (1998-11-07)
5-Methoxypsoralen, a naturally occurring linear furocoumarin, has been successfully used in combination with ultraviolet (UV) A irradiation [psoralen plus UV (PUVA)] to manage psoriasis and vitiligo. In patients and volunteers, PUVA 5-methoxypsoralen causes a dose-related increase in cutaneous photosensitivity. However
M Inzinger et al.
The British journal of dermatology, 165(3), 640-645 (2011-05-14)
Few studies have directly compared the clinical efficacy of psoralen plus ultraviolet A (PUVA) vs. biologics in the treatment of psoriasis. To compare the clinical efficacy of PUVA and biologic therapies for psoriasis under daily life conditions. Data from a
Tatsushi Goto et al.
Drug metabolism and disposition: the biological fate of chemicals, 38(12), 2110-2116 (2010-08-28)
A number of studies have demonstrated that cytochrome P450 (P450) converts furanocoumarin derivatives into reactive molecules, which form covalent bonds to biomolecules. 5-Methoxypsoralen (5-MOP) is a natural furanocoumarin from apiaceous plants. In this study, we examined the effect on 5-MOP
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