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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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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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Jinglan Han et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 34(17), 2200-2202 (2009-12-01)
To study the chemical constituents from Lobelia chinensis. The constituents were extracted with 95% EtOH, partitioned with different solvents, and isolated and purified by silica gel column chromatography and crystallization, their structures were elucidated by physico-chemical properties and spectroscopic data.
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).
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)
Earl Grey tea intoxication.
Josef Finsterer
Lancet (London, England), 359(9316), 1484-1484 (2002-05-04)
E Gorgus et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 48(1), 93-98 (2009-09-23)
Phototoxic and photo-genotoxic furocoumarins occur, e.g., in citrus species, parsnip, parsley, celery, and figs. They exhibit phototoxic and photo-genotoxic properties in combination with UV radiation, while less is known about the phototoxicity of the coumarin derivative limettin mainly found in
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