Anthrone

Chemical Properties

off-white to light yellow crystals

Uses

Used for determination of carbohydrates Anthrone is used for the determination of carbohydrates. It is used as a general reagent in the colorimetric determination of carbohydrates in yeast and plant extracts. It is involved in organic synthesis. It is utilized for the determination of sugar in body fluids. It finds application as a laxative.

Uses

Anthrone is a tricyclic aromatic ketone and related compound of anthracene. Anthrone is used as a reagent in the colorometric determination of carbohydrates.

Definition

ChEBI: A member of the class of anthracenes that is 9,10-dihydroanthracene carrying an oxo group at C-9.

General Description

Anthrone has the ability to reduce aldehyde containing reducing sugars such as streptose and N-acetyl glucosamine present in streptomycin, into acids. It develops a red- violet color. Therefore, it is used to determine streptomycin quantitatively. Anthrone has been used to detect carbohydrate containing lipids and to measure sugar content such as sucrose and trehalose in the liquid medium.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Synthesis

104g anthraquinone, 100g tin particles, 750ml glacial acetic acid mixed heated to boiling, and then add concentrated hydrochloric acid 250ml (relative density of 1.19) one by one, about 2h to add, at this time, the anthraquinone should be all dissolved in the reaction solution, otherwise, need to make up the addition of tin particles and hydrochloric acid. Then reflux 1.5h, decolorization and filtration, filtrate diluted with 100ml water, cooled to 10 , precipitated anthraquinone crystals, filtration, washed with water to make pH = 7 and get the crude crystals, dry weight of 80 g. Crude can be used to recrystallize the mixture of acetone or benzene and petroleum ether (3:1), can be obtained with melting point of 154-155 , anthraquinone of about 60 g. .

Purification Methods

This stable keto tautomer of 9-anthranol (above) provides yellow crystals from a 3:1 mixture of *C6H6/pet ether (b 60-80o) (10-12mL/g), or successively from *C6H6 then EtOH. Dry it in vacuo. [Meyer Org Synth Coll Vol I 60 1941, Beilstein 6 IV 4930.]