Xanthosine is a nucleoside derived from xanthine and ribose. It is the biosynthetic precursor to 7-methylxanthosine by the action of 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (active alkaloid in chocolate), which in turn is the precursor to caffeine, the alkaloid in coffee and tea.[3]
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Names | |
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IUPAC name
Xanthosine[2]
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Systematic IUPAC name
9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-1H-purine-2,6-dione | |
Other names
Xanthine riboside; 9-β-D-Ribofuranosylxanthine
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Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.005.164 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C10H12N4O6 | |
Molar mass | 284.228 g·mol−1 |
Melting point | Decomposes when heated |
Sparingly soluble in cold water; freely soluble in hot water | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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See also
editReferences
edit- ^ Merck Index, 11th Edition, 9974
- ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1421. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ^ Ashihara, Hiroshi; Yokota, Takao; Crozier, Alan (2013). Biosynthesis and catabolism of purine alkaloids. Advances in Botanical Research. Vol. 68. pp. 111–138. doi:10.1016/B978-0-12-408061-4.00004-3. ISBN 978-0-12-408061-4.