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[[File:DL-Erythrose.svg|thumb|left|[[Fischer projection|Fischer projections]] depicting the two enantiomers of erythrose]]
[[File:DL-Erythrose.svg|thumb|left|[[Fischer projection|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),<ref>[https://books.google.com/books?id=L_tBAAAAcAAJ&pg=PA472 Obituary of Garot] (1869) ''Journal de pharmacie et de chimie'', 4th series, '''9''' : 472-473.</ref> and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").<ref>Garot (1850) [https://books.google.com/books?id=2bQ8AAAAcAAJ&pg=PA5 "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).)</ref><ref>{{cite book|last1=Wells|first1=David Ames|last2=Cross|first2=Charles Robert|last3=Bliss|first3=George|last4=Trowbridge|first4=John|last5=Nichols|first5=William Ripley|last6=Kneeland|first6=Samuel|title=Annual of Scientific Discovery|date=1851|publisher=Gould, Kendall, and Lincoln|location=Boston|page=[https://archive.org/details/annualscientifi29crosgoog/page/n242 211]|url=https://archive.org/details/annualscientifi29crosgoog|quote=erythrose discovery.|access-date=11 December 2014}}</ref>
Erythrose was first isolated in 1849 from [[rhubarb]] by the French pharmacist Louis Feux Joseph Garot (1798-1869),<ref>[https://books.google.com/books?id=L_tBAAAAcAAJ&pg=PA472 Obituary of Garot] (1869) ''Journal de pharmacie et de chimie'', 4th series, '''9''' : 472-473.</ref> and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").<ref>Garot (1850) [https://books.google.com/books?id=2bQ8AAAAcAAJ&pg=PA5 "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).)</ref><ref>{{cite book|last1=Wells|first1=David Ames|last2=Cross|first2=Charles Robert|last3=Bliss|first3=George|last4=Trowbridge|first4=John|last5=Nichols|first5=William Ripley|last6=Kneeland|first6=Samuel|title=Annual of Scientific Discovery|date=1851|publisher=Gould, Kendall, and Lincoln|location=Boston|page=[https://archive.org/details/annualscientifi29crosgoog/page/n242 211]|url=https://archive.org/details/annualscientifi29crosgoog|quote=erythrose discovery.|access-date=11 December 2014}}</ref>


[[Erythrose 4-phosphate]] is an intermediate in the [[pentose phosphate pathway]]<ref>{{cite journal|last1=Kruger|first1=Nicholas J|last2=von Schaewen|first2=Antje|title=The oxidative pentose phosphate pathway: structure and organisation|journal=Current Opinion in Plant Biology|date=June 2003|volume=6|issue=3|pages=236–246|doi=10.1016/S1369-5266(03)00039-6|pmid=12753973}}</ref> and the [[Calvin cycle]].<ref>{{cite journal|last1=Schwender|first1=Jörg|last2=Goffman|first2=Fernando|last3=Ohlrogge|first3=John B.|last4=Shachar-Hill|first4=Yair|title=Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds|journal=Nature|date=9 December 2004|volume=432|issue=7018|pages=779–782|doi=10.1038/nature03145|pmid=15592419|bibcode=2004Natur.432..779S|s2cid=4401215}}</ref>
[[Erythrose 4-phosphate]] is an intermediate in the [[pentose phosphate pathway]]<ref>{{cite journal|last1=Kruger|first1=Nicholas J|last2=von Schaewen|first2=Antje|title=The oxidative pentose phosphate pathway: structure and organisation|journal=Current Opinion in Plant Biology|date=June 2003|volume=6|issue=3|pages=236–246|doi=10.1016/S1369-5266(03)00039-6|pmid=12753973}}</ref> and the [[Calvin cycle]].<ref>{{cite journal|last1=Schwender|first1=Jörg|last2=Goffman|first2=Fernando|last3=Ohlrogge|first3=John B.|last4=Shachar-Hill|first4=Yair|title=Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds|journal=Nature|date=9 December 2004|volume=432|issue=7018|pages=779–782|doi=10.1038/nature03145|pmid=15592419|bibcode=2004Natur.432..779S|s2cid=4401215}}</ref>

Revision as of 10:44, 3 September 2024

Erythrose[1]

D-Erythrose

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
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
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 checkY☒N ?)

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". Chemistry LibreTexts. 2015-04-01. Retrieved 2021-11-17.
  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. 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. 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.
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