Chemistry:Erythrose

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Erythrose[1]
D-erythrose.svg
D-Erythrose
L-erythrose.svg
L-Erythrose
Names
IUPAC names
(2R,3R)-2,3,4-Trihydroxybutanal (D)
(2S,3S)-2,3,4-Trihydroxybutanal (L)
Identifiers
3D model (JSmol)
5805561
ChEBI
ChemSpider
EC Number
  • 209-505-2
KEGG
UNII
Properties
C4H8O4
Molar mass 120.104 g·mol−1
Appearance Light yellow syrup
highly soluble
Hazards
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

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.[2]

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),[3] and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").[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]

See also

References

  1. ↑ Merck Index, 11th Edition, 3637
  2. ↑ "4.5: Diastereomers" (in en). 2015-04-01. https://chem.libretexts.org/Courses/University_of_Illinois_Springfield/UIS%3A_CHE_267_-_Organic_Chemistry_I_(Morsch)/Chapters/Chapter_05%3A_Stereochemistry/4.05%3A_Diastereomers. 
  3. ↑ Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
  4. ↑ 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).)
  5. ↑ 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. https://archive.org/details/annualscientifi29crosgoog. Retrieved 11 December 2014. "erythrose discovery." 
  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. 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. doi:10.1038/nature03145. PMID 15592419. Bibcode: 2004Natur.432..779S. 
  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. PMID 13345750. PMC 314578. http://jb.asm.org/content/71/6/649.long. Retrieved 11 December 2014. 



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