3-Cyanoumbelliferone

Specifications

Purity

≥98% (TLC)

Identity

1H-NMR

Appearance

Light red powder

Properties

Fluorescence

λex 408 nm, λem 450 nm in methanol

Melting Point

≥250°C (lit.)

Solvents

alcohols, DMF

Long Term Storage

+4°C

Use / Stability

Stable for at least 2 years after receipt when stored at +4°C.

Handling Advice

Protect from light and moisture.

Short Term Storage

+4°C

Shipping

AMBIENT

Transportation

Not dangerous goods

Signal word

Warning

GHS Symbol

GHS07

Precautionary statements

P261, P280, P305 + P351 + P338

Hazard statements

H302, H312, H315, H319, H332, H335

Description

Phenolic dyes with high pKas - such as 7-hydroxycoumarin (often called umbelliferone) and the more common 7-hydroxy-4-methylcoumarin - are not fully deprotonated and therefore not fully fluorescent unless the pH of the reaction mixture is raised to above pH ~10. Thus, substrates derived from these fluorophores are seldom used for continuous measurement of enzymatic activity in solution or live cells. The similar 3-cyano-7-hydroxycoumarin and 6,8-difluoro-7-hydroxy-4-methylcoumarin have lower pKas, making them suitable for a broader range of applications. Moreover, the -trifluoromethylumbelliferone product has longer-wavelength spectra and stronger absorbance than -methylumbelliferone. Ether, ester and phosphate substrates derived from these phenolic dyes may be fluorescent but invariably exhibit shorter-wavelength absorption and emission spectra.

InChi

InChI=1S/C10H5NO3/c11-5-7-3-6-1-2-8(12)4-9(6)14-10(7)13/h1-4,12H

References

(1) I.N. White et al.: Anal. Biochem. 172(2), 304 (1988)

InChi Key

IJQYTHQDUDCJEQ-UHFFFAOYSA-N

Smiles

OC1=CC=C2C=C(C#N)C(=O)OC2=C1