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Xanthone
Xanthone
IUPAC name
Other names 9-oxo-xanthene
diphenyline ketone oxide
Identifiers
CAS number 90-47-1 Yes check.svgY
SMILES
Properties
Molecular formula C13H8O2
Molar mass 196.19 g/mol
Appearance off-white solid
Melting point

174 °C, 447 K, 345 °F

Boiling point

351 °C, 624 K, 664 °F

Solubility in water sl. sol. in hot water
Hazards
R-phrases R36/37/38
S-phrases S26 S37[1]
Related compounds
Related compounds xanthene
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Xanthone is an organic compound with the molecular formula C13H8O2. It can be prepared by the heating of phenyl salicylate.[2] In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide.[3] Xanthone is also used in the preparation of xanthydrol which used in the determination of urea levels in the blood.

Xanthone derivatives

The chemical structure of xanthone forms the central core of a variety of naturally occurring organic compounds, such as mangostin, which are sometimes collectively referred to as xanthones.[4] Over 200 xanthones have been identified. Xanthones are natural constituents of plants in the families Bonnetiaceae and Clusiaceae and are found in some species in the family Podostemaceae.[5] Many of these xanthones are found in the pericarp of the mangosteen fruit (Garcinia mangostana), which can be found in the region of Southeast Asia.

Synthetic derivatives of xanthone can be added during the polymerization of polyester, to form a plastic that has a greater resistance to degradation by ultraviolet light. The most useful derivative is tetrahydroxyxanthone. Polyester film can be used for the production of third generation printed solar cells, to make them a cost effective alternative to silica-based solar energy generation. It was originally intended that the additive be used for polyester greenhouses in hot climates, where the plastic would degrade after a few years from UV exposure. The xanthone-treated product has an extended useful lifetime of ten years instead of three.

See also

References

  1. ^ MSDS from AlphaAesar
  2. ^ Organic Syntheses, Coll. Vol. 1, p.552 (1941) - preparation of xanthone
  3. ^ Steiner, L. F. and S. A. Summerland. 1943. Xanthone as an ovicide and larvicide for the codling moth. Journal of economic entomology 36, 435-439.
  4. ^ PubMed.gov - journal articles on xanthones
  5. ^ *Angiosperm Phylogeny Group (2003). An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG II. Botanical Journal of the Linnean Society 141: 399-436 (Available online: Abstract | Full text (HTML) | Full text (PDF))
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1911 encyclopedia

Up to date as of January 14, 2010

From LoveToKnow 1911

XANTHONE (dibenzo-y-pyrone, or diphenylene ketone oxide), C H 0 in organic chemistry, a heterocyclic compound containing the ring system shown below. It is obtained by the oxidation of xanthene (methylene diphenylene oxide) with chromic acid; by the action of phosphorus oxychloride on disodium salicylate; by heating 2 2'-dioxybenzophenone with concentrated sulphuric acid; by distilling fluoran with lime; by the oxidation of xanthydrol (R. Meyer, Ber., 1893, 26, p. 1277); by boiling diazotized 2.2'-diaminobenzophenone with water (Heyl., Ber., 1898, 31, p. 3 0 34); by heating salol with concentrated sulphuric acid (C. Graebe, Ann., 1889, 254, p. 280), and by heating potassium-ortho-chlorobenzoate with sodium phenolate and a small quantity of copper powder to 180-190° C. (F. Ullmann, Ber., 1905, 3 8, pp. 729, 2120, 2211). It crystallizes in needles which melt at 173-174° and boil at 349-350° C., and are volatile in steam. Its solution in concentrated sulphuric acid is of a yellow colour and shows a marked blue fluorescence. The carbonyl group is not ketonic in character since it yields neither an oxime nor hydrazone. When fused with caustic potash it yields phenol and salicylic acid. Mild reducing agents convert it into xanthydrol, the group > CO becoming > CH. OH, whilst a strong reducing agent like hydriodic acid converts it into xanthene, the group >CO becoming > CH. Phosphorus pentasulphide at 140 - I 50° C. converts it into xanthion by transformation of > CO to > CS (R. Meyer, Ber., 1900, 33, p. 2580), and this latter compound condenses with hydroxylamine to form xanthone oxime.

All four mono-hydroxyxanthones are known, and are prepared by heating salicylic acid with either resorcin, pyrocatechin or hydroquinone; they are yellow crystalline solids, which act as dyestuffs. The I. 7-dihydroxyxanthone, known as euxanthone, is prepared by heating euxanthic acid with hydrochloric acid or by heating hydroquinone carboxylic acid with 3-resorcylic acid and acetic anhydride (S. Kostanecki, Ber., 1891, 24, p. 39 8 3; C. Graebe, Ann., 1889, 2 54, p. 298). It is also obtained from Indian yellow (Graebe, ibid.),. formed in the urine of cows fed on mango leaves. It crystallizes in yellow needles which sublime readily. On fusion with caustic potash it decomposes with formation of tetrahydroxy-benzophenone, which then breaks up into resorcin and hydroquinone. The isomeric I. 6-dihydroxyxanthone, isoeuxanthone, is formed when 0-resorcylic acid is heated with acetic anhydride. Gentisein, or I . 3 . 7-trihydroxyxanthone, is found in the form of its methyl ether (gentisin) in gentian root; it is obtained synthetically by condensing phloroglucin with hydroquinone carboxylic acid.

Xanthene, C13H100, may be synthesized by condensing phenol with ortho-cresol in the presence of aluminium chloride. Its tetramethyl-diamino derivative, which is formed by condensing formaldehyde with dimethyl-meta-aminophenol and subsequent elimination of water from the resulting diphenyl methane derivative, is the leuco base of pyronine, into which it passes by oxidation.

8 6 CO 3 5 O // 3 Xanthone.

/ / CH Cl(CHs)2N/N/ O / Pyronine.


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