Compound: Ethyl maltol
SMILES: O=c1c(O)c(occ1)CC
InChIKey: YIKYNHJUKRTCJL-UHFFFAOYSA-N
Synonyms: Ethyl maltol, 2-Ethyl-3-hydroxy-4H-pyran-4-one, 4940-11-8, 2-Ethyl-3-hydroxy-4-pyrone, Ethylmaltol, Veltol plus, 3-Hydroxy-2-ethyl-4-pyrone, 2-ethyl-3-hydroxypyran-4-one, 2-Ethylpyromeconic acid, 4H-PYRAN-4-ONE, 2-ETHYL-3-HYDROXY-, 2-Ethyl pyromeconic acid, Ethyl Hydroxypyrone, FEMA No. 3487, DTXSID5041516, L6Q8K29L05, NSC638851, NSC-638851, DTXCID3021516, RefChem:138985, 225-582-5, 3-Hydroxy-2-ethyl-4H-pyran-4-one, MFCD00059795, Maltol-ethyl, 3-Hydroxy-2-ethyl-1,4-pyrone, 2-Ethyl-3-hydroxy-pyran-4-one, E637, 3-Hydroxy-2-ethyl-gamma-pyrone, EINECS 225-582-5, Ethyl maltol [NF], BRN 1618110, Ethyl maltol (Standard), 6-ethyl-3-hydroxy-2-methyl-4H-pyran-4-one, ETHYL MALTOL [II], ETHYL MALTOL [MI], ETHYL MALTOL [FCC], ETHYL MALTOL [FHFI], SCHEMBL41817, ETHYL MALTOL [VANDF], ETHYL MALTOL [MART.], UNII-L6Q8K29L05, ETHYL MALTOL [USP-RS], CHEMBL121557, INS NO.637, orb1301687, orb3139632, FEMA 3487, Ethyl maltol, analytical standard, INS-637, CHEBI:169105, HMS5085I16, 3-Hydroxy-2-ethyl-.gamma.-pyrone, HY-W010320R, Tox21_300800, BBL036457, Ethyl maltol, >=99%, FCC, FG, s6335, STL559005, AKOS015915123, CS-W011036, EBC-153037, HY-W010320, MSK001161-100M, 3-Hydroxy-2-ethyl-4-pyrone11/8/40, MSK001161-1000M, NCGC00248174-01, NCGC00254704-01, AS-13959, BP-12441, FE159267, SY016066, CAS-4940-11-8, 2-Ethyl-3-hydroxy-4H-pyran-4-one, 99%, 3-Hydroxy-2-ethyl-laquo gammaRaquo -pyrone, E-637, H0550, NS00012427, ST51038313, EN300-99262, Ethyl maltol Solution in Methanol, 100ug/mL, C20362, Ethyl maltol Solution in Methanol, 1000ug/mL, H10673, 2-Ethyl-3-hydroxy-4H-pyran-4-one; Ethyl maltol, 5-18-01-00135 (Beilstein Handbook Reference), F240479, Q930843, Z1255465165, Ethyl maltol, United States Pharmacopeia (USP) Reference Standard, Ethyl maltol, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C7H8O3
molecular_weight: 140.14 g/mol
exact_mass: 140.047344113 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 10
topological_polar_surface_area: 46.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 289.00 to 290.00 °C. @ 760.00 mm Hg
melting_point: 90 - 91 °C
solubility: Sparingly soluble in water, soluble in propylene glycol
Descriptions:
pubchem: Ethyl maltol is a pyranone.
chembl: E637 is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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. It is a white solid with a sweet smell that can be described as caramelized sugar or as caramelized fruit. Ethyl maltol is often used in perfumery to create gourmand scents. Its aroma is described as "sweet, caramellic, jammy, strawberry, cotton candy, berry, sugar". Ethyl maltol was first used in Mugler's Angel perfume in 1992.
The conjugate base derived from ethylmaltol, again like maltol, has a high affinity for iron, forming a red coordination complex.  In such compounds, the heterocycle is a bidentate ligand.
Original patent: