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116238

Sigma-Aldrich

5,7-Dimethoxycoumarin

98%

Synonym(s):

Citropten, Limettin

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About This Item

Empirical Formula (Hill Notation):
C11H10O4
CAS Number:
487-06-9
Molecular Weight:
206.19
EC Number:
207-646-4
MDL number:
MFCD00006870
UNSPSC Code:
12352100
PubChem Substance ID:
24847274
NACRES:
NA.22

assay

98%

form

solid

mp

146-149 °C (lit.)

SMILES string

COc1cc(OC)c2C=CC(=O)Oc2c1

InChI

1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3

InChI key

NXJCRELRQHZBQA-UHFFFAOYSA-N

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General description

5,7-dimethoxycoumarin is isolated and identified from leaves and fruits of Pelea anisata H. Mann, a plant whose fruit are used in the construction of mohikana leis. It induces frameshift mutagenesis in bacteria. It also causes lethal photosensitization and the formation of sister chromatid exchanges in Chinese hamster cells.

Biochem/physiol Actions

5,7-Dimethoxycoumarin induces the processes of differentiation and melanogenesis in murine (B16) and human (A375).

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Takeshi Kinoshita et al.
Chemical & pharmaceutical bulletin, 50(1), 118-120 (2002-02-05)
A new C-8 prenylated 5,7-dimethoxycoumarin named omphamurrayin was isolated from the leaves of Murraya paniculata var. omphalocarpa, and its structure was established as 5,7-dimethoxy-8-(1-oxo-2-senecioyl-3-methyl-3-butenyl)-2H-1-benzopyran-2-one on the basis of the spectroscopic evidence. The taxonomic status of M. paniculata var. omphalocarpa is
Daniela Alesiani et al.
International journal of oncology, 34(6), 1727-1735 (2009-05-09)
In this study, the processes of differentiation and melanogenesis induced by 5,7-dimethoxycoumarin in murine (B16) and human (A375) melanoma cells were investigated. Taking into account the previously demonstrated antiproliferative and differentiation activities of this compound, we examined Ras/Raf/Mek/Erk mitogen-activated protein
Isolation and characterization of the photoadducts of 5,7-dimethoxycoumarin and adenosine.
T H Cho et al.
Photochemistry and photobiology, 46(2), 305-309 (1987-08-01)
S Makki et al.
Journal of chromatography, 563(2), 407-413 (1991-02-15)
Citropten (5,7-dimethoxycoumarin) and bergapten (5-methoxypsoralen) are present in bergamot oil which is used as a tanning cosmetic product. The aim of this study was to quantify, using high-performance liquid chromatography, the amount of citropten and bergapten in the skin after
P Treffel et al.
Skin pharmacology : the official journal of the Skin Pharmacology Society, 5(2), 108-113 (1992-01-01)
It is a general rule that percutaneous absorption is increased when the site of application is occluded. In this study we compared the in vitro permeation profiles of two molecules with different physicochemical properties under occluded versus unoccluded conditions. Human
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