You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-11 17:50:34 UTC
Update Date2016-02-11 02:08:14 UTC
HMDB IDHMDB32572
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethylparaben
DescriptionMethylparaben is found in alcoholic beverages. Methylparaben is an antimicrobial agent, preservative, flavouring agent. Methylparaben is a constituent of cloudberry, yellow passion fruit, white wine, botrytised wine and Bourbon vanilla Methylparaben has been shown to exhibit anti-microbial function (PMID 12866935 ). Methylparaben belongs to the family of Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
4-Hydroxybenzoic acid methyl esterChEBI
e 218ChEBI
e218ChEBI
FEMA no. 2710ChEBI
INS no. 218ChEBI
INS number 218ChEBI
MaseptolChEBI
MetabenChEBI
MethabenChEBI
Methyl butexChEBI
Methyl chemoseptChEBI
Methyl P-hydroxybenzoateChEBI
Methyl parabenChEBI
MetoxydeChEBI
MoldexChEBI
NipaginChEBI
P-CarbomethoxyphenolChEBI
P-Hydroxybenzoic acid methyl esterChEBI
P-MethoxycarbonylphenolChEBI
P-OxybenzoesauremethylesterChEBI
ParidolChEBI
PreservalChEBI
SeptosChEBI
SolbrolChEBI
Tegosept mChEBI
4-Hydroxybenzoate methyl esterGenerator
Methyl parahydroxybenzoic acidGenerator
Methyl P-hydroxybenzoic acidGenerator
P-Hydroxybenzoate methyl esterGenerator
4-(Methoxycarbonyl)phenolHMDB
Benzoic acid, 4-hydroxy-, methyl esterHMDB
Benzoic acid, P-hydroxy-, methyl esterHMDB
Methyl 4-hydroxybenzoateHMDB
Methyl ester OF P-hydroxybenzoic acidHMDB
Methyl P-oxybenzoateHMDB
Methyl paraseptHMDB
Methyl-P-hydroxybenzoateHMDB
Nipagin mHMDB
P-Hydroxybenzoic acid, methyl esterHMDB
P-Hydroxybenzoic methyl esterHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Namemethyl 4-hydroxybenzoate
Traditional Nameparaben
CAS Registry Number99-76-3
SMILES
COC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
InChI KeyInChIKey=LXCFILQKKLGQFO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Benzylether
  • Benzoyl
  • Phenol
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • anti-microbial
Application
  • Flavoring Agent
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point131 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.5 mg/mL at 25 °CNot Available
LogP1.96Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.69 mg/mLALOGPS
logP2.17ALOGPS
logP1.67ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.06 m3·mol-1ChemAxon
Polarizability15.15 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00di-7900000000-42b2fb742e91f0c75f63View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.0480 (0.0424-0.0545) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.0328 (0.0265-0.0406) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB010509
KNApSAcK IDC00030771
Chemspider ID7176
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB32572
Metagene LinkHMDB32572
METLIN IDNot Available
PubChem Compound7456
PDB IDMPB
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gupta S, Kaisheva E: Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques. AAPS PharmSci. 2003;5(2):E8. [12866935 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.