Umbelliferone

Structural formula
General
Surname	Umbelliferone
other names	7-hydroxycoumarin 7-hydroxy-2 H -chromen-2-one
Molecular formula	C 9 H 6 O 3
Brief description	yellow needles
External identifiers / databases
CAS number 93-35-6 EC number 202-240-3 ECHA InfoCard 100.002.038 PubChem 5281426 ChemSpider 4444774 Wikidata Q416196
properties
Molar mass	162.15 g · mol -1
Physical state	firmly
Melting point	226-229 ° C (dec.)
solubility	Easily soluble in ethanol , chloroform and glacial acetic acid poorly soluble in water
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Umbelliferone (also: Hydrangin ) is a hydroxy - derivative of coumarin and a natural substance.

Occurrence

Lovage ( Levisticum officinale )

Umbelliferone is often found in plants of the umbelliferae (Apiaceae), e.g. B. Lovage before. In UV light it shows a clear blue fluorescence .

use

Umbelliferone serves as a pH indicator in the range from 6.5 to 8.9, in the form of a 0.1% aqueous solution as fluorescence - an indicator for the detection of calcium - and copper ions.

It is used in sunscreens and as an optical brightener for textiles, and it is also used as a laser dye . Synthetic 7- O- glycosides are used for the fluorimetric determination of glycosidases .

synthesis

Umbelliferone can be produced from resorcinol and malic acid using the Pechmann reaction .

Individual evidence

1. ↑ ^{a b c d} Entry on umbelliferone. In: Römpp Online . Georg Thieme Verlag, accessed on November 14, 2014.
2. ↑ ^{a b c d} data sheet umbelliferone (PDF) from Merck , accessed on December 25, 2019.
3. ↑ ^{a b} P. Drosky et al. The optical brighteners Fraxin and Aesculin ChiuZ 2014, 48, pp. 450–459