Acetoin

Acetoin
Names
	Preferred IUPAC name 3-Hydroxybutan-2-one
	Other names 3-Hydroxybutanone; Acetyl methyl carbinol
Identifiers
CAS Number	513-86-0 (R/S) ; 53584-56-8 (R) ; 78183-56-9 (S) ;
3D model (JSmol)	Interactive image; (R): Interactive image; (S): Interactive image;
ChEBI	CHEBI:15688 ; CHEBI:15686 (R); CHEBI:15687 (S);
ChemSpider	21105851 ; 388445 (R); 394765 (S);
ECHA InfoCard	100.007.432
EC Number	208-174-1;
KEGG	C00466; C00810 (R); C01769 (S);
PubChem CID	179; 439314 (R); 447765 (S);
RTECS number	EL8790000;
UNII	BG4D34CO2H ;
CompTox Dashboard (EPA)	DTXSID0024399 ;
	InChI InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 Key: ROWKJAVDOGWPAT-UHFFFAOYSA-N ; InChI=1/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 Key: ROWKJAVDOGWPAT-UHFFFAOYAD;
	SMILES CC(=O)C(C)O; (R): CC(=O)[C@@H](C)O; (S): CC(=O)[C@H](C)O;
Properties
Chemical formula	C4H8O2
Molar mass	88.106 g·mol−1
Appearance	colorless liquid
Odor	bland, yogurt-like
Density	1.012 g/cm3
Melting point	15 °C (59 °F; 288 K)
Boiling point	148 °C (298 °F; 421 K)
Solubility in water	1000 g/L (20 °C)
Solubility in other solvents	Soluble in alcohol ; Slightly soluble in ether, petroleum ether ; Miscible in propylene glycol ; Insoluble in vegetable oil
log P	−0.36
Acidity (pKa)	13.72
Chiral rotation ([α]D)	−39.4
Refractive index (nD)	1.4171
Hazards
Flash point	41 °C (106 °F; 314 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	> 5000 mg/kg (rat, oral)
Safety data sheet (SDS)	MSDS
	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

Acetoin, also known as 3-hydroxybutanone or acetyl methyl carbinol, is an organic compound with the formula CH₃CH(OH)C(O)CH₃. It is a colorless liquid with a pleasant, buttery odor. It is chiral. The form produced by bacteria is (R)-acetoin.

Names

Preferred IUPAC name 3-Hydroxybutan-2-one
Other names 3-Hydroxybutanone Acetyl methyl carbinol
Identifiers
CAS Number	513-86-0 (R/S)^Y 53584-56-8 (R)^Y 78183-56-9 (S)^Y
3D model (JSmol)	Interactive image (R): Interactive image (S): Interactive image
ChEBI	CHEBI:15688^Y CHEBI:15686 (R) CHEBI:15687 (S)
ChemSpider	21105851^Y 388445 (R) 394765 (S)
ECHA InfoCard	100.007.432
EC Number	208-174-1
KEGG	C00466 C00810 (R) C01769 (S)
PubChem CID	179 439314 (R) 447765 (S)
RTECS number	EL8790000
UNII	BG4D34CO2H^Y
CompTox Dashboard (EPA)	DTXSID0024399
InChI InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3^Y Key: ROWKJAVDOGWPAT-UHFFFAOYSA-N^Y InChI=1/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 Key: ROWKJAVDOGWPAT-UHFFFAOYAD
SMILES CC(=O)C(C)O (R): CC(=O)[C@@H](C)O (S): CC(=O)[C@H](C)O
Properties
Chemical formula	C₄H₈O₂
Molar mass	88.106 g·mol⁻¹
Appearance	colorless liquid
Odor	bland, yogurt-like
Density	1.012 g/cm³
Melting point	15 °C (59 °F; 288 K)
Boiling point	148 °C (298 °F; 421 K)
Solubility in water	1000 g/L (20 °C)
Solubility in other solvents	Soluble in alcohol Slightly soluble in ether, petroleum ether Miscible in propylene glycol Insoluble in vegetable oil
log P	−0.36
Acidity (pK_a)	13.72
Chiral rotation ([α]_D)	−39.4
Refractive index (n_D)	1.4171
Hazards
Flash point	41 °C (106 °F; 314 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	> 5000 mg/kg (rat, oral)
Safety data sheet (SDS)	MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references