All Photos(1)
Synonym(s):
9(10H)-Anthracenone
Empirical Formula (Hill Notation):
C14H10O
CAS Number:
Molecular Weight:
194.23
Beilstein:
1910173
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
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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.
Regulatory Information
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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)
The estimation of carbohydrates in plant extracts by anthrone.
Yemm EW and Willis AJ.
The Biochemical Journal, 57(3), 508-508 (1954)
Antioxidant activity of anthraquinones and anthrone.
Yen GC, et al.
Food Chemistry, 70(4), 437-441 (2000)
Fredyc Diaz et al.
Journal of natural products, 67(3), 352-356 (2004-03-27)
Cytotoxicity-based, bioassay-guided fractionation of the chloroform-soluble extracts of both the roots and leaves of Picramnia latifolia led to the isolation of two new anthrone C-glycosides, picramniosides G (1) and H (2), two new oxanthrone C-glycosides, mayosides D (3) and E
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