Erythrose (original) (raw)
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Erythrose[1]
 D-Erythrose |
|
|---|---|
 L-Erythrose |
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| Names | |
| IUPAC names D-Erythrose D-_erythro_-Tetrose (systematic name)[2] | |
| Systematic IUPAC name (2_R_,3_R_)-2,3,4-Trihydroxybutanal (D)(2_S_,3_S_)-2,3,4-Trihydroxybutanal (L) | |
| Identifiers | |
| CAS Number | 583-50-6 (D)  Y533-49-3 (L) Y |
| 3D model (JSmol) | (D): Interactive image(L): Interactive image |
| Beilstein Reference | 5805561 |
| ChEBI | CHEBI:27904 Y |
| ChemSpider | 84990 (D) Y |
| ECHA InfoCard | 100.008.643  |
| EC Number | 209-505-2 |
| KEGG | C01796 |
| PubChem CID | 94176 (D) |
| UNII | X3EI0WE8Q4 (D) Y96DH71781X (L) Y |
| CompTox Dashboard (EPA) | DTXSID601318240 |
| InChI InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1 YKey: YTBSYETUWUMLBZ-IUYQGCFVSA-N YInChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1Key: YTBSYETUWUMLBZ-IUYQGCFVBI |
|
| SMILES (D): OC[C@@H](O)[C@@H](O)C=O(L): OC[C@H](O)[C@H](O)C=O | |
| Properties | |
| Chemical formula | C4H8O4 |
| Molar mass | 120.104 g·mol−1 |
| Appearance | Light yellow syrup |
| Solubility in water | highly soluble |
| Hazards | |
| NFPA 704 (fire diamond) |  1 1 0 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).  Y verify (what is Y N ?) Infobox references |
Chemical compound
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]
Fischer projections depicting the two enantiomers of erythrose
Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869),[4] and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").[5][6]
Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway[7] and the Calvin cycle.[8]
Oxidative bacteria can be made to use erythrose as its sole energy source.[9]
Although often inconsequential, erythrose in aqueous solution mainly exists as the hydrate owing to the following equilibrium:[10]
HOCH2CH(OH)CH(OH)CHO + H2O ⇌ HOCH2CH(OH)CH(OH)CH(OH)2
- ^ Merck Index, 11th Edition, 3637
- ^ https://iupac.qmul.ac.uk/2carb/08n09.html
- ^ "4.5: Diastereomers". Chemistry LibreTexts. 2015-04-01. Retrieved 2021-11-17.
- ^ Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
- ^ Garot (1850) "De la matière colorante rouge des rhubarbes exotiques et indigènes et de son application (comme matière colorante) aux arts et à la pharmacie" (On the red coloring material of exotic and indigenous rhubarb and on its application (as a coloring material) in the arts and in pharmacy), Journal de Pharmacie et de Chimie, 3rd series, 17 : 5-19. Erythrose is named on p. 10: "Celui que je propose, sans y attacher toutefois la moindre importance, est celui d'érythrose, du verbe grec 'ερυθραινω, rougir (1)." (The one [i.e., name] that I propose, without attaching any importance to it, is that of erythrose, from the Greek verb ερυθραινω, to redden (1).)
- ^ Wells, David Ames; Cross, Charles Robert; Bliss, George; Trowbridge, John; Nichols, William Ripley; Kneeland, Samuel (1851). Annual of Scientific Discovery. Boston: Gould, Kendall, and Lincoln. p. 211. Retrieved 11 December 2014. erythrose discovery.
- ^ Kruger, Nicholas J; von Schaewen, Antje (June 2003). "The oxidative pentose phosphate pathway: structure and organisation". Current Opinion in Plant Biology. 6 (3): 236–246. doi:10.1016/S1369-5266(03)00039-6. PMID 12753973.
- ^ Schwender, Jörg; Goffman, Fernando; Ohlrogge, John B.; Shachar-Hill, Yair (9 December 2004). "Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds". Nature. 432 (7018): 779–782. Bibcode:2004Natur.432..779S. doi:10.1038/nature03145. PMID 15592419. S2CID 4401215.
- ^ Hiatt, Howard H; Horecker, B L (13 October 1955). "D-erythrose metabolism in a strain of Alcaligenes faecalis". Journal of Bacteriology. 71 (6): 649–654. doi:10.1128/jb.71.6.649-654.1956. PMC 314578. PMID 13345750. Retrieved 11 December 2014.
- ^ Angyal, SJ; Wheen, RG (1980). "The Composition of Reducing Sugars in Aqueous Solution : Glyceraldehyde, Erythrose, Threose". Australian Journal of Chemistry. 33 (5): 1001. doi:10.1071/CH9801001.