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275727

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:
Molecular Weight:
216.19
Beilstein:
19560
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

Quality Level

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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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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
Shinsuke Marumoto et al.
Journal of agricultural and food chemistry, 58(13), 7777-7781 (2010-06-10)
The biotransformation of bergapten (1) by the fungus Glomerella cingulata gave the corresponding reduced acid, 6,7-furano-5-methoxy hydrocoumaric acid (2), a new compound. Xanthotoxin (3) was also converted to the corresponding reduced acid cnidiol b (4) and demethylated metabolite xanthotoxol (5)
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
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
S Tzaneva et al.
The British journal of dermatology, 162(3), 655-660 (2009-09-23)
Ultraviolet (UV) A1 and psoralen plus UVA (PUVA) are effective treatment options for severe atopic dermatitis (AD); however, their relative efficacy has not yet been determined in a head-to-head study. To compare UVA1 and oral 5-methoxypsoralen (5-MOP) plus UVA with

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