Erythrose

Erythrose ^[1]

D-Erythrose
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
CAS Number	583-50-6 (D) Y 533-49-3 (L) Y
3D model (JSmol)	(D): Interactive image (L): Interactive image
Beilstein Reference	5805561
ChEBI	CHEBI:27904  Y
ChemSpider	84990 (D) Y
ECHA InfoCard	100.008.643
EC Number	209-505-2
KEGG	C01796
PubChem CID	94176  (D)
UNII	X3EI0WE8Q4  (D) Y 96DH71781X  (L) Y
CompTox Dashboard (EPA)	DTXSID601318240
InChI InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1 Y Key: YTBSYETUWUMLBZ-IUYQGCFVSA-N Y InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1 Key: YTBSYETUWUMLBZ-IUYQGCFVBI
SMILES (D):OC[C@@H](O)[C@@H](O)C=O (L):OC[C@H](O)[C@H](O)C=O
Properties
Chemical formula	C4H8O4
Molar mass	120.104 g·mol−1
Appearance	Light yellow syrup
Solubility in water	highly soluble
Hazards
NFPA 704 (fire diamond)	1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

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]

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), ^[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]

HOCH₂CH(OH)CH(OH)CHO + H₂O ⇌ HOCH₂CH(OH)CH(OH)CH(OH)₂

See also

• Erythritol

References

1. Merck Index, 11th Edition, 3637
2. https://iupac.qmul.ac.uk/2carb/08n09.html
3. "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. 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. 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.
8. 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. 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. 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.