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Erythrose

From Wikipedia, the free encyclopedia
Erythrose[1]
BERJAYA
D-Erythrose
BERJAYA
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)
5805561
ChEBI
ChemSpider
ECHA InfoCard 100.008.643 Edit this at Wikidata
EC Number
  • 209-505-2
KEGG
UNII
  • InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1 checkY
    Key: YTBSYETUWUMLBZ-IUYQGCFVSA-N checkY
  • InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1
    Key: YTBSYETUWUMLBZ-IUYQGCFVBI
  • (D): OC[C@@H](O)[C@@H](O)C=O
  • (L): OC[C@H](O)[C@H](O)C=O
Properties
C4H8O4
Molar mass 120.104 g·mol−1
Appearance Light yellow syrup
highly soluble[vague]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

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]

BERJAYA
Fischer projections depicting the two enantiomers of erythrose

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

[edit]

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]

See also

[edit]

References

[edit]
  1. ↑ Merck Index, 11th Edition, 3637
  2. ↑ "2-Carb-8 and 2-Carb-9".
  3. ↑ "4.5: Diastereomers". Chemistry LibreTexts. 2015-04-01. Retrieved 2021-11-17.
  4. ↑ Fischer, Emil; Tafel, Julius (March 31, 1887). "Oxydation der mehrwerthigen Alkohole". Berichte der Deutschen Chemischen Gesellschaft. 20. Deutsche Chemische Gesellschaft: 1088–1094. doi:10.1002/cber.188702001243. Retrieved July 17, 2026.
  5. ↑ Fischer, Emil (July 1890). "Synthesen in der Zuckergruppe". Berichte der Deutschen Chemischen Gesellschaft. 2408. Deutsche Chemische Gesellschaft: 1765–3851. doi:10.1002/cber.18900230268. Retrieved July 17, 2026.
  6. ↑ 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. Bibcode:2003COPB....6..236K. doi:10.1016/S1369-5266(03)00039-6. PMID 12753973.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
  11. ↑ 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).)
  12. ↑ 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.
  13. ↑ Tschirch, A.; Heuberger, K. (October 12, 1902). "Untersuchungen über den chinesischen Rhabarber". Archiv der Pharmazie. 2408. Deutsche Pharmazeutische Gesellschaft: 561–640. doi:10.1002/ardp.19022400805. Retrieved July 17, 2026.
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