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368512

Sigma-Aldrich

7-Hydroxy-4-(trifluoromethyl)coumarin

98%

Synonym(s):

4-(Trifluoromethyl)umbelliferone

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About This Item

Empirical Formula (Hill Notation):
C10H5F3O3
CAS Number:
575-03-1
Molecular Weight:
230.14
Beilstein:
210932
MDL number:
MFCD00037578
UNSPSC Code:
12352103
PubChem Substance ID:
24862915
NACRES:
NA.23

Assay

98%

form

solid

pKa 

7.26

mp

178-180 °C (lit.)

fluorescence

λex 385 nm; λem 502 nm in methanol

SMILES string

Oc1ccc2c(OC(=O)C=C2C(F)(F)F)c1

InChI

1S/C10H5F3O3/c11-10(12,13)7-4-9(15)16-8-3-5(14)1-2-6(7)8/h1-4,14H

InChI key

CCKWMCUOHJAVOL-UHFFFAOYSA-N

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General description

7-Hydroxy-4-(trifluoromethyl)coumarin is a class of 7-hydroxycoumarin that is majorly used as laser dyes. It has a characterized emission spectra and may be used in excited state proton transfer (ESPT).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300,H315,H319,H335

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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Sean Ekins et al.
Drug metabolism and disposition: the biological fate of chemicals, 31(9), 1077-1080 (2003-08-16)
CYP2D6 and CYP3A4 represent two particularly important members of the cytochrome p450 enzyme family due to their involvement in the metabolism of many commercially available drugs. Avoiding potent inhibitory interactions with both of these enzymes is highly desirable in early
Base-induced phototautomerization in 7-hydroxy-4-(trifluoromethyl) coumarin
Westlake BC, et al.
The Journal of Physical Chemistry B, 116(51), 14886-14891 (2012)
Risto O Juvonen et al.
Xenobiotica; the fate of foreign compounds in biological systems, 50(8), 885-893 (2020-01-07)
Sulfonation is an important high affinity elimination pathway for phenolic compounds.In this study sulfonation of 7-hydroxycoumarin and 13 its derivatives were evaluated in liver cytosols of human and six animal species. 7-hydroxycoumarin and its derivatives are strongly fluorescent, and their
Hideto Jinno et al.
Drug metabolism and disposition: the biological fate of chemicals, 31(5), 528-532 (2003-04-16)
UDP-glucuronosyltransferase (UGT) 1A10 is an isoform of UGT1A, which is expressed in extrahepatic, biliary and aerodigestive/gastrointestinal tissues. We have previously reported two nonsynonymous single nucleotide polymorphisms in exon 1 of human UGT1A10 gene; 177G>A and 605C>T resulting in amino acid
S Ekins et al.
Pharmacogenetics, 7(3), 165-179 (1997-06-01)
7-Ethoxy-4-trifluoromethylcoumarin (7-EFC) was examined as a substrate for cytochrome P450 (P450) in microsomes from human livers and expressed in B-lymphoblastoid cells. The O-deethylation of 7-EFC to 7-hydroxy-4-trifluoromethylcoumarin (7-HFC) varied over a liver bank (n = 19) by a factor of
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