Erythrose

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Erythrose[1]
D-erythrose.svg
D-Erythrose
150px
L-Erythrose
Names
IUPAC names
(2R,3R)-2,3,4-Trihydroxybutanal (D)
(2S,3S)-2,3,4-Trihydroxybutanal (L)
Identifiers
583-50-6 (D) YesY
533-49-3 (L) YesY
ChEBI CHEBI:27904 YesY
ChemSpider 84990 (D) YesY
Jmol 3D model (D): Interactive image
(L): Interactive image
PubChem 94176 (D)
  • InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1 YesY
    Key: YTBSYETUWUMLBZ-IUYQGCFVSA-N YesY
  • 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 120.10 g·mol−1
Appearance Light yellow syrup
Very soluble
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Erythrose is a tetrose carbohydrate with the chemical formula C4H8O4. It has one aldehyde group, and so is part of the aldose family. The natural isomer is D-erythrose.

File:DL-Erythrose.svg
Fischer projections

Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869),[2] and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").[3][4]

Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway[5] and the Calvin cycle.[6]

Erythrulose, an isomer of erythrose, is non-toxic.[7]

Oxidative bacteria can be made to use erythrose as its sole energy source.[8]

References

  1. Merck Index, 11th Edition, 3637
  2. Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
  3. 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).)
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  7. National Industrial Chemicals Notification and Assessment Scheme (NICNAS). Erythrulose. 'Australia February 11, 2008.
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