Anthrone

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Anthrone
Skeletal formula Anthrone.png
Skeletal formula
Ball-and-stick model Anthrone-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
Anthracen-9(10H)-one
Other names
  • Carbothrone
  • 9-Oxoanthracene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.813 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2 Yes check.svgY
    Key: RJGDLRCDCYRQOQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2
    Key: RJGDLRCDCYRQOQ-UHFFFAOYAA
  • O=C2c1c(cccc1)Cc3c2cccc3
Properties
C14H10O
Molar mass 194.233 g·mol−1
AppearanceWhite to light yellow needles
Melting point 155 to 158 °C (311 to 316 °F; 428 to 431 K)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates. [1]

Derivatives of anthrone are used in pharmacy as laxative. They stimulate the motion of the colon and reduce water reabsorption. Some anthrone derivatives can be extracted from a variety of plants, including Rhamnus frangula , Aloe ferox , Rheum officinale , and Cassia senna . [2] Glycosides of anthrone are also found in high amounts in rhubarb leaves, and alongside concentrated amounts of oxalic acid are the reason for the leaves being inedible.

Synthesis and reactions

Anthrone can be prepared from anthraquinone by reduction with tin or copper. [3]

An alternative synthesis involves cyclization of o-benzylbenzoic acid induced with hydrogen fluoride. [4]

Anthrone syntheses Anthrone synthesis.svg
Anthrone syntheses

Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment. [5]

Tautomeric equilibrium for anthrone. Anthrol-AnthroneEq.svg
Tautomeric equilibrium for anthrone.

Anthrone is the more stable tautomer relative to the anthrol as has been established also by X-ray crystallography. [6] The tautomeric equilibrium is estimated at 100 in aqueous solution. For the two other isomeric anthrols, the tautomeric equilibrium is reversed: they are phenolic. [7]

Anthrone undergoes nitration using conventional conditions for aromatic nitration, implying that it is the hydroxy tautomer that is the reactant. [8]

References

  1. ↑ Trevelyan, W. E.; Forrest, RS; Harrison, JS (1952). "Determination of Yeast Carbohydrates with the Anthrone Reagent". Nature. 170 (4328): 626–627. Bibcode:1952Natur.170..626T. doi:10.1038/170626a0. PMID   13002392. S2CID   4184596.
  2. ↑ Niaz, Kamal; Khan, Fazlullah (2020-01-01), Sanches Silva, Ana; Nabavi, Seyed Fazel; Saeedi, Mina; Nabavi, Seyed Mohammad (eds.), "Chapter 3 - Analysis of polyphenolics" , Recent Advances in Natural Products Analysis, Elsevier, pp. 39–197, doi:10.1016/b978-0-12-816455-6.00003-2, ISBN   978-0-12-816455-6 , retrieved 2024-06-01
  3. ↑ Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses. 14: 4. doi:10.15227/orgsyn.014.0004.
  4. ↑ Fieser, Louis F.; Hershberg, E. B. (May 1939). "Inter- and Intramolecular Acylations with Hydrogen Fluoride". Journal of the American Chemical Society. 61 (5): 1272–1281. Bibcode:1939JAChS..61.1272F. doi:10.1021/ja01874a079.
  5. ↑ Bien, H.-S.; Stawitz, J.; Wunderlich, K. (2005). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355. ISBN   978-3-527-30673-2.
  6. ↑ Lian, Jian-Jou; Lin, Chung-Chang; Chang, Hsu-Kai; Chen, Po-Chiang; Liu, Rai-Shung (2006). "Thermal and Metal-Catalyzed Cyclization of 1-Substituted 3,5-Dien-1-ynes via a [1,7]-Hydrogen Shift: Development of a Tandem Aldol Condensation−Dehydration and Aromatization Catalysis between 3-En-1-yn-5-al Units and Cyclic Ketones". Journal of the American Chemical Society. 128 (30): 9661–9667. Bibcode:2006JAChS.128.9661L. doi:10.1021/ja061203b. PMID   16866518.
  7. ↑ Ośmiałowski, Borys; Raczyńska, Ewa D.; Krygowski, Tadeusz M. (2006). "Tautomeric Equilibria and Pi Electron Delocalization for Some Monohydroxyarenes Quantum Chemical Studies". The Journal of Organic Chemistry. 71 (10): 3727–3736. doi:10.1021/jo052615q. PMID   16674042.
  8. ↑ Kurt H. Meyer (1928). "Nitroanthrone". Organic Syntheses. 8: 78. doi:10.15227/orgsyn.008.0078.
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