Ethyl maltol

Ethyl maltol
Names
	Preferred IUPAC name 2-Ethyl-3-hydroxy-4H-pyran-4-one
	Other names 2-Ethyl-3-hydroxy-4-pyranone; 2-Ethyl pyromeconic acid; 2-Ethyl-3-hydroxy-4-pyrone;
Identifiers
CAS Number	4940-11-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:169105;
ChEMBL	ChEMBL121557 ;
ChemSpider	19804 ;
ECHA InfoCard	100.023.256
EC Number	225-582-5;
KEGG	C20362;
PubChem CID	21059;
RTECS number	UQ0840000;
UNII	L6Q8K29L05 ;
CompTox Dashboard (EPA)	DTXSID5041516 ;
	InChI InChI=1S/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3 Key: YIKYNHJUKRTCJL-UHFFFAOYSA-N ; InChI=1/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3 Key: YIKYNHJUKRTCJL-UHFFFAOYAY;
	SMILES CCC1=C(C(=O)C=CO1)O;
Properties
Chemical formula	C7H8O3
Molar mass	140.138 g·mol−1
Appearance	White crystalline powder
Melting point	85 to 95 °C (185 to 203 °F; 358 to 368 K)
Boiling point	161 °C (322 °F; 434 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330, P501
	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

Ethyl maltol is an organic compound that is a common flavourant in some confectioneries. It is related to the more common flavorant maltol by replacement of the methyl group by an ethyl group.^[2] It is a white solid with a sweet smell that can be described as caramelized sugar or as caramelized fruit.

The conjugate base derived from ethylmaltol, again like maltol, has a high affinity for iron, forming a red coordination complex^{[citation needed]}. In such compounds, the heterocycle is a bidentate ligand.

Original patent:^[3]

References

^ Ethyl maltol at Sigma-Aldrich
^ Erich Lück and Gert-Wolfhard von Rymon Lipinski "Foods, 3. Food Additives" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a11_561
^ Charles R Stephens Jr & Robert P Allingham, U.S. patent 3,446,629 (1969 to Pfizer Inc).

[1] Ethyl maltol at Sigma-Aldrich

[2] Erich Lück and Gert-Wolfhard von Rymon Lipinski "Foods, 3. Food Additives" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a11_561

[3] Charles R Stephens Jr & Robert P Allingham, U.S. patent 3,446,629 (1969 to Pfizer Inc).

[1]

[2]

[3]

Names

Preferred IUPAC name 2-Ethyl-3-hydroxy-4H-pyran-4-one
Other names 2-Ethyl-3-hydroxy-4-pyranone 2-Ethyl pyromeconic acid 2-Ethyl-3-hydroxy-4-pyrone
Identifiers
CAS Number	4940-11-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:169105
ChEMBL	ChEMBL121557^Y
ChemSpider	19804^Y
ECHA InfoCard	100.023.256
EC Number	225-582-5
KEGG	C20362
PubChem CID	21059
RTECS number	UQ0840000
UNII	L6Q8K29L05^Y
CompTox Dashboard (EPA)	DTXSID5041516
InChI InChI=1S/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3^Y Key: YIKYNHJUKRTCJL-UHFFFAOYSA-N^Y InChI=1/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3 Key: YIKYNHJUKRTCJL-UHFFFAOYAY
SMILES CCC1=C(C(=O)C=CO1)O
Properties
Chemical formula	C₇H₈O₃
Molar mass	140.138 g·mol⁻¹
Appearance	White crystalline powder
Melting point	85 to 95 °C (185 to 203 °F; 358 to 368 K)^[1]
Boiling point	161 °C (322 °F; 434 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330, P501
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