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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-23 11:14:42 UTC
Update Date2017-12-07 01:46:16 UTC
HMDB IDHMDB0001868
Secondary Accession Numbers
  • HMDB01868
Metabolite Identification
Common Name5-Methoxysalicylic acid
Description5-methoxysalicylic acid, also known as 2-hydroxy-5-methoxybenzoate or 5-methoxy-2-hydroxybenzoate, belongs to M-methoxybenzoic acids and derivatives class of compounds. Those are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. 5-methoxysalicylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 5-methoxysalicylic acid can be found in herbs and spices and tea, which makes 5-methoxysalicylic acid a potential biomarker for the consumption of these food products. 5-methoxysalicylic acid can be found primarily in blood and urine, as well as in human red blood cell tissue. 5-Methoxysalicylic acid is a chemical compound. It is a component of castoreum, the exudate from the castor sacs of the mature beaver (Wikipedia). enhance intestinal absorption of insulin in rats and insulin uptake into human red blood cells (PMID 6319944 )..
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-5-methoxybenzoateHMDB
2-Hydroxy-5-methoxybenzoic acidHMDB
5-Methoxy-2-hydroxybenzoateHMDB
5-Methoxy-2-hydroxybenzoic acidHMDB
5-MethoxysalicylateHMDB
6-Hydroxy-m-anisateHMDB
6-Hydroxy-m-anisic acidHMDB
6-Methoxy-m-anisateHMDB
6-Methoxy-m-anisic acidHMDB
5-Methoxysalicylic acid, sodium saltMeSH
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-5-methoxybenzoic acid
Traditional Name5-methoxysalicylic acid
CAS Registry Number2612-02-4
SMILES
COC1=CC(C(O)=O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)
InChI KeyIZZIWIAOVZOBLF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • 4-alkoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.38 g/LALOGPS
logP1.85ALOGPS
logP1.82ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.8 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0v4i-1900000000-1e109eb0ee8ae327f133View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0092-3290000000-b2c04fbea10000b9034eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-02t9-2900000000-eca7c3623a7975e733d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-5900000000-5aaba4f93b26c36dfcb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fvl-9100000000-94c4137aab8bf06f3617View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negativesplash10-0udi-0901000000-077381dba9d80706a097View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positivesplash10-0fri-0930000000-4e24b1261f33fba704e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0529000000-a613547802dab4125d68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0529000000-a613547802dab4125d68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0529000000-a613547802dab4125d68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0529000000-a613547802dab4125d68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0900000000-e2d69678bf5361774dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0pvi-0900000000-46471751a79101b1fd39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0900000000-e2d69678bf5361774dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0pvi-0900000000-46471751a79101b1fd39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0900000000-7ee52209d923d99f69efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-d2f3d14888f1a31ec2c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c1-9300000000-1ba0741166e840d38463View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-2c570bf0fdb5915da23aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0900000000-77290f37ff3e5699255aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-b642574365d90b34c12cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Red Blood Cell
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.14 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified8.294 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB011959
    KNApSAcK IDNot Available
    Chemspider ID68296
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia Link5-Methoxysalicylic acid
    METLIN ID4164
    PubChem Compound75787
    PDB IDNot Available
    ChEBI ID545920
    References
    Synthesis ReferenceNagasawa, Masaaki; Nishioka, Hiroyasu; Suzuki, Takanori; Nagano, Eiichi; Ishii, Katsuyuki; Nakao, Ryu. Preparation of salicylic acids from 2-methoxybenzoic acids. Jpn. Kokai Tokkyo Koho (2000), 6 pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Nishihata T, Higuchi T, Kamada A: Possible mechanism of uptake for several compounds in ionized form through human erythrocyte membrane. Life Sci. 1984 Jan 30;34(5):427-36. [PubMed:6694531 ]
    2. Nishihata T, Higuchi T, Kamada A: Salicylate-promoted permeation of cefoxitin, insulin and phenylalanine across red cell membrane. Possible mechanism. Life Sci. 1984 Jan 30;34(5):437-45. [PubMed:6319944 ]