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A91205

Sigma-Aldrich

Anthrone

96%

Synonym(s):

9(10H)-Anthracenone

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About This Item

Empirical Formula (Hill Notation):
C14H10O
CAS Number:
Molecular Weight:
194.23
Beilstein:
1910173
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:

Assay

96%

mp

154-157 °C (lit.)

SMILES string

O=C1c2ccccc2Cc3ccccc13

InChI

1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2

InChI key

RJGDLRCDCYRQOQ-UHFFFAOYSA-N

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General description

Anthrone (a tricyclic aromatic ketone) on mixing with sulfuric acid forms anthrone reagent, which is widely used in the estimation of sugars. Anthrone shows an inhibitory effect on the peroxidation of linoleic acid. It undergoes Michael addition with cinnamaldehyde in the presence of proline or prolinol derivatives.

Application

Anthrone has been used in colorimetric anthrone assay. It may be used to prepare azomethines by reacting with amines.

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Asymmetric organocatalytic anthrone additions to activated alkenes.
Zea A, et al.
Tetrahedron, 67(14), 2513-2529 (2011)
Synthesis of azomethines of anthrone.
Nadkarny VV and Sanzgiri MN.
J. Ind. Chem. Soc., 67(6), 513-514 (1990)
Antioxidant activity of anthraquinones and anthrone.
Yen GC, et al.
Food Chemistry, 70(4), 437-441 (2000)
The estimation of carbohydrates in plant extracts by anthrone.
Yemm EW and Willis AJ.
The Biochemical Journal, 57(3), 508-508 (1954)
Leo C James et al.
Proceedings of the National Academy of Sciences of the United States of America, 102(36), 12730-12735 (2005-09-01)
Induced fit is a predominant phenomenon in protein-ligand interactions, yet it is invariably attributed without establishing the existence, let alone the structure, of the initial, low-affinity encounter complex. We determined the crystal structure of the encounter complex on the pathway

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