Erythrose

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Erythrose[1]
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D-Erythrose
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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
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3D model (JSmol)
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5805561
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  • 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[<span title="Script error: No such module "decodeEncode".">vague]
Hazards
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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).
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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]

File:DL-Erythrose.svg
Fischer projections depicting the two enantiomers of erythrose

Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis-Félix-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]

Page Module:Chem2/styles.css has no content.HOCH2CH(OH)CH(OH)CHO + H2O ⇌ HOCH2CH(OH)CH(OH)CH(OH)2

See also

References

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  1. ^ Merck Index, 11th Edition, 3637
  2. ^ Page Module:Citation/CS1/styles.css has no content."2-Carb-8 and 2-Carb-9".
  3. ^ Page Module:Citation/CS1/styles.css has no content."4.5: Diastereomers". Chemistry LibreTexts. 2015-04-01. Retrieved 2021-11-17.
  4. ^ Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
  5. ^ 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).)
  6. ^ Page Module:Citation/CS1/styles.css has no content.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.
  7. ^ Page Module:Citation/CS1/styles.css has no content.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.
  8. ^ Page Module:Citation/CS1/styles.css has no content.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.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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.
  10. ^ Page Module:Citation/CS1/styles.css has no content.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.

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