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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

Quality Level

100

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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Daniela Alesiani et al.
International journal of oncology, 32(2), 425-434 (2008-01-19)
In the present study we investigated the antiproliferative activity of 5,7-dimethoxycoumarin on the murine B16 and human A375 melanoma cell lines. The inhibitory concentration 50 (IC50) was estimated for each cell line by preliminary assay of tetrazolium salt reduction (MTT).
Earl Grey tea intoxication.
Josef Finsterer
Lancet (London, England), 359(9316), 1484-1484 (2002-05-04)
Ewa Chodurek et al.
Cellular & molecular biology letters, 17(4), 616-632 (2012-09-25)
Malignant melanoma (melanoma malignum) is one of the most dangerous types of tumor. It is very difficult to cure. In recent years, a lot of attention has been given to chemoprevention. This method uses natural and synthetic compounds to interfere
D Chouchi et al.
Journal of chromatography. A, 672(1-2), 177-183 (1994-06-24)
Generally on the gas chromatogram of a volatile essential oil, terpenes, oxygenated compounds and sesquiterpenes appear. With temperature programming, it was shown that some non-volatiles are present with the volatiles. They are simple coumarin (2H-1-benzopyran-2-one) derivatives such as citropten (5,7-dimethoxycoumarin)
Tomonori Nakamura et al.
Journal of natural medicines, 63(1), 15-20 (2008-07-09)
We have investigated the structure-activity relationship between 63 natural oxycoumarin derivatives and their effects on the expression of inducible-nitric oxide synthase (iNOS) induced by lipopolysaccharide. The protein expression of iNOS was screened by Western blot analysis, and four 5,7-dimethoxycoumarins were
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