Erythrose

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^[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[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 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]

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

See also

• Erythritol