Erythrose

Erythrose ^[1]

Haworth projection of alpha-D-erythrofuranose
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[ vague ]
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 named after the sugar alcohol erythritol (Erythrit), from which it was first synthesized in 1887 by Emil Fischer and Julius Tafel. ^{[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]

Although often inconsequential, erythrose in aqueous solution mainly exists as the hydrate owing to the following equilibrium: ^[9]

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

Unrelated compound

An unrelated compound, initially also named "erythrose", was isolated in 1849 from nitrated rhubarb by the French pharmacist Louis-Félix-Joseph Garot (1798–1869), ^[10] and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red"). ^{[11] [12]} . This unrelated substance from rhubarb is identical to the nitrated anthraquinone chrysaminic acid (Chrysaminsäure, 517-92-0 ). ^[13]

See also

• Erythritol
• Erythrulose

References

1. Merck Index, 11th Edition, 3637
2. "2-Carb-8 and 2-Carb-9".
3. "4.5: Diastereomers". Chemistry LibreTexts. 2015-04-01. Retrieved 2021-11-17.
4. Fischer, Emil; Tafel, Julius (March 31, 1887). "Oxydation der mehrwerthigen Alkohole". Berichte der Deutschen Chemischen Gesellschaft. 20. Deutsche Chemische Gesellschaft: 1088–1094. doi:10.1002/cber.188702001243 . Retrieved July 17, 2026.
5. Fischer, Emil (July 1890). "Synthesen in der Zuckergruppe". Berichte der Deutschen Chemischen Gesellschaft. 2408. Deutsche Chemische Gesellschaft: 1765–3851. doi:10.1002/cber.18900230268 . Retrieved July 17, 2026.
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. Bibcode:2003COPB....6..236K. 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.
9. 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.
10. Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
11. 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).)
12. 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.
13. Tschirch, A.; Heuberger, K. (October 12, 1902). "Untersuchungen über den chinesischen Rhabarber". Archiv der Pharmazie. 2408. Deutsche Pharmazeutische Gesellschaft: 561–640. doi:10.1002/ardp.19022400805 . Retrieved July 17, 2026.