Erythrose

Erythrose
	D-Erythrose
	L-Erythrose
Names
	IUPAC names D-Erythrose; D-erythro-Tetrose (systematic name)
	Systematic IUPAC name (2R,3R)-2,3,4-Trihydroxybutanal (D); (2S,3S)-2,3,4-Trihydroxybutanal (L)
Identifiers
CAS Number	583-50-6 (D) ; 533-49-3 (L) ;
3D model (JSmol)	(D): Interactive image; (L): Interactive image;
Beilstein Reference	5805561
ChEBI	CHEBI:27904 ;
ChemSpider	84990 (D) ;
ECHA InfoCard	100.008.643
EC Number	209-505-2;
KEGG	C01796;
PubChem CID	94176 (D);
UNII	X3EI0WE8Q4 (D) ; 96DH71781X (L) ;
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 Key: YTBSYETUWUMLBZ-IUYQGCFVSA-N ; 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). verify (what is ?) 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.

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

Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway and the Calvin cycle.

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

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

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

Names
D-Erythrose
L-Erythrose
IUPAC names D-Erythrose D-erythro-Tetrose (systematic name)
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