Compound: ZINGERONE
SMILES: O=C(CCc1cc(OC)c(O)cc1)C
InChIKey: OJYLAHXKWMRDGS-UHFFFAOYSA-N
Synonyms: ZINGERONE, Vanillylacetone, 122-48-5, Zingiberone, 4-(4-Hydroxy-3-methoxyphenyl)butan-2-one, 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, Zingherone, Gingerone, Vanillyl acetone, 2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-, [0]-Paradol, 4-Hydroxy-3-methoxybenzylacetone, 3-Methoxy-4-hydroxybenzylacetone, (4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone, (0)-Paradol, 4-(3-Methoxy-4-hydroxyphenyl)-2-butanone, FEMA No. 3124, 2-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone, DTXSID8047420, NSC-15335, 4MMW850892, DTXCID6027420, CHEBI:68657, 0 paradol, RefChem:196097, 204-548-3, NSC 15335, MFCD00048232, UNII-4MMW850892, Vanillylacetone;Gingerone, 4-(4-hydroxy-3-methoxy-phenyl)-butan-2-one, CHEMBL25894, 3-Methoxy-4-hydroxy-benzylacetone, (O)-Paradol, CCRIS 2036, HSDB 1064, EINECS 204-548-3, BRN 2051099, vanillylaceton, Zincbacitracin, AI3-31837, 0-paradol, [0]Paradol, Zingerone (Standard), Zingerone [M+H]+, ZINGERONE [FCC], ZINGERONE [MI], ZINGERONE [FHFI], ZINGERONE [HSDB], 4-(4-hydroxy-3-methoxy-phenyl)butan-2-one, 4-08-00-01866 (Beilstein Handbook Reference), SCHEMBL119051, orb1300526, orb3140118, Vanillylacetone, >=96%, FG, VANILLYLACETON [WHO-DD], SCHEMBL29378477, FEMA 3124, 4-(4-hydroxy-3-methoxyphenyl)-, HMS3651E22, MSK40217, NSC15335, Tox21_302493, BDBM50304073, EBC-47353, HY-14621R, s2371, SBB071427, STL564783, AKOS009462778, CCG-208511, DB15589, FV05929, Vanillylacetone, >=98%, natural, FG, Zingerone, analytical reference material, NCGC00256663-01, AC-34331, AS-65368, CAS-122-48-5, HY-14621, ST092341, SY017980, 4(4-Hydroxy-3-methoxyphenyl)-2-butanone, 4-(3-methoxy-4-hydroxyphenyl)butan-2-one, DB-003808, 4-(4-hydroxy-3-methoxy-phenyl)-2-butanone, CS-0003480, H1314, NS00013332, SW219618-1, C17497, EN300-1721864, F464499, SR-05000013705, Q1064625, SR-05000013705-1, BRD-K33510429-001-02-3, BRD-K33510429-001-03-1, 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 9CI, 8CI, Z1255442373, InChI=1/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H
Theoretical properties:
molecular_formula: C11H14O3
molecular_weight: 194.23 g/mol
exact_mass: 194.094294304 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 14
topological_polar_surface_area: 46.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from acetone, petroleum ether, ether plus petroleum ether
color: Crystals from acetone, petroleum ether, ether plus petroleum ether
odor: STRONG, PUNGENT ODOR REMINISCENT OF GINGER
boiling_point: 187-188 °C @ 14 mm Hg
melting_point: 40.5 °C
density: 1.138-1.139 @ 25 °C
solubility: Sparingly sol in water, petroleum ether; sol in ether, dil alkalies
flash_point: APPROX 102 °C
Descriptions:
pubchem: Zingerone is a methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger. It has a role as an antioxidant, a flavouring agent, a fragrance, an antiemetic, a radiation protective agent, an anti-inflammatory agent and a plant metabolite. It is a monomethoxybenzene, a member of phenols and a methyl ketone.
chebi: A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.
chembl: ZINGERONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Zingerone, also called vanillylacetone, is a major flavor component of ginger, providing the sweet flavor of cooked ginger. Zingerone is a crystalline solid that is sparingly soluble in water and soluble in ether. 
Zingerone is similar in chemical structure to other flavor chemicals such as vanillin and eugenol. It is used as a flavor additive in spice oils and in perfumery to introduce spicy aromas.
Fresh ginger does not contain zingerone, but it is produced by cooking or drying of the ginger root, which causes a reverse aldol reaction on gingerol.