Compound: MALTOL
SMILES: O=c1c(O)c(occ1)C
InChIKey: XPCTZQVDEJYUGT-UHFFFAOYSA-N
Synonyms: MALTOL, 118-71-8, 3-Hydroxy-2-methyl-4-pyrone, 3-Hydroxy-2-methyl-4H-pyran-4-one, Larixinic acid, Palatone, Larixic acid, Talmon, Vetol, Veltol, Corps praline, 4H-Pyran-4-one, 3-hydroxy-2-methyl-, 3-hydroxy-2-methylpyran-4-one, 2-Methyl pyromeconic acid, 2-Methyl-3-hydroxy-4-pyrone, 2-Methylpyromeconic acid, 2-Methyl-3-hydroxypyrone, 3-Hydroxy-2-methyl-gamma-pyrone, 2-Methyl-3-oxy-gamma-pyrone, FEMA No. 2656, NSC 2829, NSC-2829, NSC-404458, DTXSID0025523, Ins no.636, Ins-636, BRN 0112169, 3A9RD92BS4, AI3-18547, E-636, DTXCID305523, Laxarinic Acid, RefChem:800821, 204-271-8, 3-Hydroxy-2-methyl-pyran-4-one, Maltol (natural), MFCD00006578, 3-Hydroxy-2-methylpyrone, 2-methyl-3-hydroxy-4-pyranone, 3-Hydroxy-2-methyl-4-pyranone, NSC2829, 3-Hydroxy-2-methyl-1,4-pyrone, 3-Hydroxy-2-methyl-.gamma.-pyrone, MLS000069412, CHEBI:69438, 5-Hydroxy-6-methyl-4H-pyran-4-one, Maltol (3-Hydroxy-2-methyl-4-pyrone), E636, SMR000059093, WLN: T6O DVJ B1 CQ, CAS-118-71-8, Maltol [NF], CCRIS 3467, EINECS 204-271-8, UNII-3A9RD92BS4, methyl maltol, Laricinic acid, Maltol (Standard), Spectrum_001419, Opera_ID_338, SpecPlus_000443, MALTOL [FHFI], MALTOL [FCC], MALTOL [USP-RS], Spectrum2_001795, Spectrum3_001351, Spectrum4_001871, Spectrum5_000462, MALTOL [II], MALTOL [MI], MALTOL [MART.], bmse000538, Maltol, analytical standard, SCHEMBL4815, 3-Hydroxy-2-pyran-4-one, BSPBio_003161, KBioGR_002365, KBioSS_001899, SPECTRUM310025, 5-18-01-00114 (Beilstein Handbook Reference), MLS001424145, MLS002415738, 3-Hydroxy-2-methyl-g-pyrone, CHEMBL31422, DivK1c_006539, 3-hydroxy-2-methylpyr-4-one, Pantoprazole Sodium Impurity X, SPBio_001749, orb1301706, orb3025379, QSPL 180, 2-Methyl-3-oxy-.gamma.-pyrone, 3-hydroxy-2-methyl-4-oxopyrane, 3-hydroxyl-2-methyl-4-pyranone, FEMA 2656, HSDB 8320, KBio1_001483, KBio2_001899, KBio2_004467, KBio2_007035, KBio3_002381, XPCTZQVDEJYUGT-UHFFFAOYSA-, MSK3256, 3-hydroxy-2-methyl-gamma -pyrone, HMS2052K09, HMS3394K09, HMS5084A03, KUC106764N, HY-W012788R, STR01642, Tox21_202215, Tox21_300118, BBL011669, BDBM50227434, CCG-38443, EBC-46297, Maltol, natural, >=98.5%, FG, NSC404458, s4940, SBB055954, STK801686, 2-methyl-3-hydroxy-4H-pyran-4-one, Maltol, >=99.0%, FCC, FG, 3-Hydroxy-2-methyl-4-pyrone, 99%, AKOS005607790, CS-W013504, FM04338, HY-W012788, NC00350, PS-4578, SDCCGMLS-0066563.P001, NCGC00091223-01, NCGC00091223-02, NCGC00091223-03, NCGC00091223-04, NCGC00091223-05, NCGC00178231-01, NCGC00254046-01, NCGC00259764-01, BP-11468, KSC-11-228-8, NCI60_002320, SY011358, DB-002512, M0673, NS00012803, ST50330599, EN300-93557, F068773, Q420648, SR-01000712383, SR-01000712383-3, BRD-K40619305-001-12-1, Z1255382969, Maltol, United States Pharmacopeia (USP) Reference Standard, InChI=1/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3, 3-Hydroxy-2-methyl-4-pyrone; 3-Hydroxy-2-methyl-pyran-4-one; Maltol; Deferiprone Impurity B
Theoretical properties:
molecular_formula: C6H6O3
molecular_weight: 126.11 g/mol
exact_mass: 126.031694049 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 9
topological_polar_surface_area: 46.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Monoclinic prisms from chloroform, orthorhombic bypyramidal crystals + monoclinic prisms from 50% alcohol
color: Monoclinic prisms from chloroform, orthorhombic bypyramidal crystals + monoclinic prisms from 50% alcohol
odor: Fragrant, caramel-like odor
boiling_point: 199 °F at 760 mmHg (Sublimes) (NTP, 1992)
melting_point: 324 to 327 °F (NTP, 1992)
solubility: 1 to 10 mg/mL at 72 °F (NTP, 1992)
vapor_pressure: 0.000507 [mmHg]
Descriptions:
pubchem: 3-hydroxy-2-methyl-4-pyrone is a member of 4-pyranones. It has a role as a metabolite.
chembl: MALTOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
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: