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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:50:34 UTC
Update Date2017-12-07 03:19:44 UTC
HMDB IDHMDB0032572
Secondary Accession Numbers
  • HMDB32572
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 vanill
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 KeyLXCFILQKKLGQFO-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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

Role

Indirect biological role:

Industrial application:

  Food and nutrition:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.06 m³·mol⁻¹ChemAxon
Polarizability15.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4900000000-5aa5692082b66b714b5dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-5900000000-f3eccc0d6c2c948bd57bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4900000000-c5ef5603a5b5d1102f5aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-3ed4794b0abcfd130f36View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4920000000-b5bddbd000212b52d3e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e340d9e85783b175426eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-9f98d629ade444f4fbb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9500000000-32f5caf98f5ad60ffa16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-781a1ddebbdbcc9b39adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-41cbbcb3f2de007616e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-7900000000-f51bfe0dca5a352b0e11View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-7900000000-42b2fb742e91f0c75f63View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Saliva
  • Sweat
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>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
BiofluidStatusValueAgeSexConditionReferenceDetails
SweatDetected but not Quantified Infant (0-1 year old)Not Specifiedscreen-positive CF details
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 LinkMethylparaben
METLIN IDNot Available
PubChem Compound7456
PDB IDMPB
ChEBI ID31835
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. [PubMed:12866935 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .