Xanthone

Last updated
Xanthone
Xanthone.svg
Xanthone-3D-balls.png
Names
Preferred IUPAC name
9H-Xanthen-9-one
Other names
9-Oxoxanthene
Diphenyline ketone oxide
Identifiers
3D model (JSmol)
140443
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.816 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-997-7
166003
PubChem CID
UNII
  • InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H Yes check.svgY
    Key: JNELGWHKGNBSMD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
    Key: JNELGWHKGNBSMD-UHFFFAOYAA
  • O=C1c2ccccc2Oc3ccccc31
Properties
C13H8O2
Molar mass 196.205 g·mol−1
Appearancewhite solid
Melting point 174 °C (345 °F; 447 K)
Sl. sol. in hot water
-108.1·10−6 cm3/mol
Hazards
GHS labelling: [1]
GHS-pictogram-skull.svg
Danger
H301
P264, P270, P301+P310, P321, P330, P405, P501
Related compounds
Related compounds
xanthene
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 ?)

Xanthone is an organic compound with the molecular formula C13H8O2. It is a white solid.

Contents

In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide. [2] Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood. [3] It can also be used as a photocatalyst. [4]

Synthesis

Xanthone can be prepared by the heating of phenyl salicylate: [5]

Xanthone synthesis.svg

Six methods have been reported for synthesizing xanthone derivatives: [6]

Xanthone derivatives

Xanthone forms the core of a variety of natural products, such as mangostin or lichexanthone. These compounds are sometimes referred to as xanthones or xanthonoids. Over 200 natural xanthones have been identified. Many are phytochemicals found in plants in the families Bonnetiaceae, Clusiaceae, and Podostemaceae. [7] They are also found in some species of the genus Iris. [8] Some xanthones are found in the pericarp of the mangosteen fruit ( Garcinia mangostana) as well as in the bark and timber of Mesua thwaitesii . [9]

See also

Related Research Articles

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Pyrimidine is an aromatic, heterocyclic, organic compound similar to pyridine. One of the three diazines, it has nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine and pyridazine.

Urea, also called carbamide, is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups joined by a carbonyl functional group. It is thus the simplest amide of carbamic acid.

Combinatorial chemistry comprises chemical synthetic methods that make it possible to prepare a large number of compounds in a single process. These compound libraries can be made as mixtures, sets of individual compounds or chemical structures generated by computer software. Combinatorial chemistry can be used for the synthesis of small molecules and for peptides.

<span class="mw-page-title-main">Uracil</span> Chemical compound of RNA

Uracil is one of the four nucleobases in the nucleic acid RNA. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine (T). Uracil is a demethylated form of thymine.

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant. Most chloromethane is biogenic.

<span class="mw-page-title-main">Carbamate</span> Chemical group (>N–C(=O)–O–)

In organic chemistry, a carbamate is a category of organic compounds with the general formula R2NC(O)OR and structure >N−C(=O)−O−, which are formally derived from carbamic acid. The term includes organic compounds, formally obtained by replacing one or more of the hydrogen atoms by other organic functional groups; as well as salts with the carbamate anion H2NCOO.

<span class="mw-page-title-main">Hydrogen peroxide - urea</span> Chemical compound

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<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

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<span class="mw-page-title-main">Xanthydrol</span> Organic compound derived from xanthone reduction

Xanthydrol is an organic chemical compound. Its formula is C13H10O2. Its total molecular weight is 198.221 g/mol. Xanthydrol is used to test the levels of urea in the bloodstream.

<span class="mw-page-title-main">Selenourea</span> Chemical compound

Selenourea is the organoselenium compound with the chemical formula Se=C(NH2)2. It is a white solid. This compound features a rare example of a stable, unhindered carbon-selenium double bond. The compound is used in the synthesis of selenium heterocycles. Selenourea is a selenium analog of urea O=C(NH2)2. Few studies have been done on the compound due to the instability and toxicity of selenium compounds. Selenourea is toxic if inhaled or consumed.

Mesua thwaitesii, is a plant species in the family Calophyllaceae. It is native to Sri Lanka and southwestern India. The Sinhalese people of Sri Lanka call it "Diya Nā - දිය නා". The plant is highly valuable as a medicinal plant within the country.

<span class="mw-page-title-main">Trifluoroperacetic acid</span> Chemical compound

Trifluoroperacetic acid is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF
3
COOOH
. It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons.

<span class="mw-page-title-main">Lichexanthone</span> Chemical compound found in some lichens

Lichexanthone is an organic compound in the structural class of chemicals known as xanthones. Lichexanthone was first isolated and identified by Japanese chemists from a species of leafy lichen in the 1940s. The compound is known to occur in many lichens, and it is important in the taxonomy of species in several genera, such as Pertusaria and Pyxine. More than a dozen lichen species have a variation of the word lichexanthone incorporated as part of their binomial name. The presence of lichexanthone in lichens causes them to fluoresce a greenish-yellow colour under long-wavelength UV light; this feature is used to help identify some species. Lichexanthone is also found in several plants, and some species of fungi that do not form lichens.

References

  1. "Xanthone". pubchem.ncbi.nlm.nih.gov.
  2. 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.
  3. Bowden, R. S. T. (1962). "The Estimation of Blood Urea by the Xanthydrol Reaction". Journal of Small Animal Practice. 3 (4): 217–218. doi:10.1111/j.1748-5827.1962.tb04191.x.
  4. Romero, Nathan A.; Nicewicz, David A. (10 June 2016). "Organic Photoredox Catalysis". Chemical Reviews. 116 (17): 10075–10166. doi:10.1021/acs.chemrev.6b00057. PMID   27285582.
  5. A. F. Holleman (1927). "Xanthone". Org. Synth. 7: 84. doi:10.15227/orgsyn.007.0084.
  6. Diderot, Noungoue Tchamo; Silvere, Ngouela; Etienne, Tsamo (2006). "Xanthones as therapeutic agents: chemistry and pharmacology". In Khan, M.T.H.; Ather, A. (eds.). Lead Molecules from Natural Products: Discovery and New Trends. Advances in Phytomedicine. Elsevier Science. pp. 284–285. ISBN   978-0-08-045933-2.
  7. "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 (4): 399–436. 2003. doi:10.1046/j.1095-8339.2003.t01-1-00158.x.
  8. Williams, C.A; Harborne, J.B.; Colasante, M. (2000). "The pathway of chemical evolution in bearded iris species based on flavonoid and xanthone patterns" (PDF). Annali di Botanica. 58: 51–54. Retrieved 28 October 2015.
  9. Bandaranayake, Wickramasinghe M.; Selliah, Sathiaderan S.; Sultanbawa, M.Uvais S.; Games, D.E. (1975). "Xanthones and 4-phenylcoumarins of Mesua thwaitesii". Phytochemistry. 14 (1): 265–269. Bibcode:1975PChem..14..265B. doi:10.1016/0031-9422(75)85052-7.