Dithioerythritol

Dithioerythritol
Names
	Preferred IUPAC name (2R,3S)-1,4-Bis(sulfanyl)butane-2,3-diol
	Other names (2R,3S)-1,4-Dimercaptobutane-2,3-diol (no longer recommended); 2,3-Dihydroxybutane-1,4-dithiol; Erythro-2,3-dihydroxy-1,4-butanedithiol; Erythro-1,4-dimercapto-2,3-butanediol; Cleland's reagent (also used for DTT)
Identifiers
CAS Number	6892-68-8 ;
3D model ( JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:17456 ;
ChemSpider	388475 ;
ECHA InfoCard	100.027.271
PubChem CID	439352;
UNII	R4SVL81GQI ;
CompTox Dashboard (EPA)	DTXSID40884341 ;
	InChI InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+ Key: VHJLVAABSRFDPM-ZXZARUISSA-N ; InChI=1/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+ Key: VHJLVAABSRFDPM-ZXZARUISBS;
	SMILES C([C@@H]([C@@H](CS)O)O)S; SC[C@@H](O)[C@@H](O)CS;
Properties
Chemical formula	C4H10O2S2
Molar mass	154.253 g/mol
Melting point	82 to 84 °C (180 to 183 °F; 355 to 357 K)
	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

Dithioerythritol (DTE) is a sulfur containing sugar alcohol derived from the corresponding 4-carbon monosaccharide erythrose. It is an epimer of dithiothreitol (DTT). The molecular formula for DTE is C₄H₁₀O₂S₂.

Chemical properties

DTE is a

crystalline solid soluble in water and alcohols.^[1]^[2]

Applications

Like DTT, DTE makes an excellent

disulfide bonds. The reduction potential of DTE is the same as for DTT, about –0.331 mV.^[2] The pK_a values of the thiol groups of DTE are 9.0 and 9.9, which is higher than the corresponding values for DTT (9.3 and 9.5).^[2] Since reduction of disulfide bonds requires thiolate (ionized thiol), DTE is less efficient at lower pH compared to DTT.^[2]

Reduction with DTE is slower than with DTT. This is presumably because the orientation of the OH groups in its cyclic

trans to each other, whereas they are cis to each other in DTE.^[3]