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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:
484-20-8
Molecular Weight:
216.19
Beilstein:
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

Signal Word

Warning

Hazard Statements

H317,H341,H351

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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)
Wei Yang et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 878(5-6), 575-582 (2010-02-02)
A sensitive, specific and rapid liquid chromatography-mass spectrometry (LC-MS) method has been developed and validated for the simultaneous determination of xanthotoxin (8-methoxypsoralen), psoralen, isoimpinellin (5,8-dimethoxypsoralen) and bergapten (5-methoxypsoralen) in rat plasma using pimpinellin as an internal standard (IS). The plasma
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
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