Kethoxal

Kethoxal (3-ethoxy-1,1-dihydroxy-2-butanone) is an organic compound that has antiviral and anaplasmosis properties.^[1][3] It also forms a stable covalent adduct with guanine, which makes it useful for nucleic acid structure determination.^[4]

Kethoxal

Names
IUPAC name 3-Ethoxy-1,1-dihydroxy-2-butanone
Other names 3-Ethoxy-2-oxobutyraldehyde hydrate
Identifiers
CAS Number	27762-78-3 Y 3688-37-7 (anhydrous) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:59052
ChemSpider	31346
ECHA InfoCard	100.215.334
KEGG	D04651
MeSH	C005135
PubChem CID	34006
UNII	E00MDP82S4 Y 2HAV7G194P (anhydrous) Y
CompTox Dashboard (EPA)	DTXSID90950449
InChI InChI=1S/C6H12O4/c1-3-10-4(2)5(7)6(8)9/h4,6,8-9H,3H2,1-2H3 Key: YRCRRHNVYVFNTM-UHFFFAOYSA-N
SMILES CCOC(C)C(=O)C(O)O
Properties
Chemical formula	C6H12O4
Molar mass	148.158 g·mol−1
Appearance	Pale yellow syrup[1]
Boiling point	145 °C (293 °F; 418 K)[1][2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nucleic acid binding

Kethoxal, as with other 1,2-dicarbonyl compounds,^[5] reacts with nucleic acids. It has high specificity for guanine over other ribonucleotides. In whole RNA, it reacts preferentially with guanine residues that are not involved in hydrogen-bonding.^[6][7] It can thus be used to probe the interactions involved with the secondary structure and other binding interactions of RNA^[8] and help with nucleic acid sequence analysis. The binding is reversible, which allows the kethoxal to be removed and the original RNA recovered.^{[citation needed]}