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Identification
YMDB IDYMDB01688
NameEthyl-4-hydroxybenzoate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthylparaben, also known as e-214 or aseptin a, belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. Ethylparaben is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethylparaben is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 4-(Ethoxycarbonyl)phenol
  • 4-Carbethoxyphenol
  • 4-Hydroxybenzoic acid, ethyl ester
  • Aseptin a
  • Aseptine a
  • Aseptoform E
  • Benzoic acid, 4-hydroxy-, ethyl ester
  • Benzoic acid, p-hydroxy-, ethyl ester
  • Bonomold OE
  • Easeptol
  • Ester etylowykwasu p-hydroksybenzoesowego
  • Ethyl 4-hydroxybenzoate
  • Ethyl Butex
  • Ethyl p-hydroxybenzoate
  • Ethyl p-oxybenzoate
  • Ethyl para-hydroxybenzoate
  • Ethyl paraben
  • Ethyl parasept
  • Ethylester kyseliny p-hydroxybenzoove
  • Ethylparaben
  • Keloform
  • Mycocten
  • Napagin A
  • Nipagin A
  • Nipagina A
  • Nipazin A
  • p-Carbethoxyphenol
  • p-Hydroxybenzoate ethyl ester
  • p-Hydroxybenzoic acid ethyl ester
  • p-Hydroxybenzoic acid, ethyl ester
  • p-Hydroxybenzoic ethyl ester
  • p-Oxybenzoesaeureaethylester
  • Para-hydroxybenzoic acid ethyl ester
  • Sobrol A
  • Solbrol A
  • Tegosept E
  • 4-Hydroxybenzoic acid ethyl ester
  • e-214
  • e214
  • Ethyl parahydroxybenzoate
  • 4-Hydroxybenzoate ethyl ester
  • Ethyl p-hydroxybenzoic acid
  • Ethyl parahydroxybenzoic acid
  • Ethyl chemosept
  • Ethyl-4-hydroxybenzoate
  • Ethyl-p-hydroxybenzoate
  • Ethylparaben, inn, usan
  • Mekkings e
  • Ethyl hydroxybenzoic acid
CAS number120-47-8
WeightAverage: 166.1739
Monoisotopic: 166.062994186
InChI KeyNUVBSKCKDOMJSU-UHFFFAOYSA-N
InChIInChI=1S/C9H10O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3
IUPAC Nameethyl 4-hydroxybenzoate
Traditional IUPAC Nameethylparaben
Chemical FormulaC9H10O3
SMILESCCOC(=O)C1=CC=C(O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parentp-Hydroxybenzoic acid alkyl esters
Alternative Parents
Substituents
  • P-hydroxybenzoic acid alkyl ester
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point117 °C
Experimental Properties
PropertyValueReference
Water Solubility0.885 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogP2.47 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.49 g/LALOGPS
logP2.76ALOGPS
logP2.03ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.81 m³·mol⁻¹ChemAxon
Polarizability17.23 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
MildFDB010510
PhenolicFDB010510
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-2900000000-489a671c1deb7c34c07bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00y0-3900000000-c1ca8c4a3e26621c8959JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-6900000000-6a0e4e400b0c9ced0ae9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-2900000000-489a671c1deb7c34c07bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00y0-3900000000-c1ca8c4a3e26621c8959JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-6900000000-6a0e4e400b0c9ced0ae9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3900000000-7c9963244828bfd6dc09JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-2910000000-520330358fe2a32ba595JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0900000000-026024910ee96b0887cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0900000000-9a9b6e693b1424978dceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0900000000-2e5dbef1d0fad386068fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0900000000-59447059cdee325cfc8aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014r-0900000000-3eb9e5cfcd05f833bb11JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0900000000-026024910ee96b0887cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0900000000-9a9b6e693b1424978dceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0900000000-2e5dbef1d0fad386068fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0900000000-59447059cdee325cfc8aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0072-7900000000-2570ac4f0cac9ddf3e64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00dj-9800000000-568849783aecc83f7c2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-5e9f881d152f5b3fa0beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-caa573c6bab6939082d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0072-7900000000-2570ac4f0cac9ddf3e64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00dj-9800000000-568849783aecc83f7c2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-5e9f881d152f5b3fa0beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-caa573c6bab6939082d2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-5edabab1a6ee50991a47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-1900000000-608dc4a8887a0295554fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9400000000-ba68420db383fea306c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-3e62aae4552f1c87f2a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-8afb30175a5535ef38edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9400000000-48796a631e1530fccfe2JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00di-4900000000-890e881678f1ceddd23eJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID31575
HMDB IDHMDB0032573
Pubchem Compound ID8434
Kegg IDNot Available
ChemSpider ID13846749
FOODB IDFDB010510
WikipediaEthylparaben
BioCyc IDNot Available