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368512

Sigma-Aldrich

7-Hydroxy-4-(trifluoromethyl)coumarin

98%

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Synonym(s):
4-(Trifluoromethyl)umbelliferone
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

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)

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Base-induced phototautomerization in 7-hydroxy-4-(trifluoromethyl) coumarin
Westlake BC, et al.
The Journal of Physical Chemistry B, 116(51), 14886-14891 (2012)
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
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
Anima Ghosal et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(2), 267-271 (2004-01-28)
Posaconazole (Noxafil, SCH 56592), an orally available broad-spectrum triazole antifungal, is currently in phase III clinical studies for treating serious opportunistic fungal infections. The major in vitro metabolite of posaconazole formed by human liver microsomes supplemented with uridine 5'-diphosphate-glucuronic acid
Brian Dean et al.
Archives of biochemistry and biophysics, 426(1), 55-62 (2004-05-08)
Two UDP-glucuronosyltransferases (UGT2B9(*)2 and UGT2B33) have been isolated from female rhesus monkey liver. Microsomal preparations of the cell lines expressing the UGTs catalyzed the glucuronidation of the general substrate 7-hydroxy-4-(trifluoromethyl)coumarin in addition to selected estrogens (beta-estradiol and estriol) and opioids
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