Erythrose
Chemical compound
From Wikipedia, the free encyclopedia
Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose; it is a diastereomer of D-threose.[3]
 D-Erythrose | |
 L-Erythrose | |
| Names | |
|---|---|
| IUPAC names
D-Erythrose D-erythro-Tetrose (systematic name)[2] | |
| Systematic IUPAC name
(2R,3R)-2,3,4-Trihydroxybutanal (D) (2S,3S)-2,3,4-Trihydroxybutanal (L) | |
| Identifiers | |
3D model (JSmol) |
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| 5805561 | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.008.643 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII |
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CompTox Dashboard (EPA) |
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| Properties | |
| C4H8O4 | |
| Molar mass | 120.104 g·mol−1 |
| Appearance | Light yellow syrup |
| highly soluble[vague] | |
| Hazards | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Erythrose was named after the sugar alcohol erythritol (Erythrit), from which it was first synthesized in 1887 by Emil Fischer and Julius Tafel. [4][5]
Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway[6] and the Calvin cycle.[7]
Oxidative bacteria can be made to use erythrose as its sole energy source.[8]
Although often inconsequential, erythrose in aqueous solution mainly exists as the hydrate owing to the following equilibrium:[9]
- HOCH2CH(OH)CH(OH)CHO + H2O ⇌ HOCH2CH(OH)CH(OH)CH(OH)2
Unrelated compound
An unrelated compound, initially also named "erythrose", was isolated in 1849 from nitrated rhubarb by the French pharmacist Louis-Félix-Joseph Garot (1798–1869),[10] and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").[11][12]. This unrelated substance from rhubarb is identical to the nitrated anthraquinone chrysaminic acid (Chrysaminsäure, 517-92-0 ).[13]