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Record Information
Version3.6
Creation Date2006-05-22 14:17:35 UTC
Update Date2017-08-16 03:53:24 UTC
HMDB IDHMDB0002085
Secondary Accession Numbers
  • HMDB02085
Metabolite Identification
Common NameSyringic acid
DescriptionSyringic acid is a phenol present in some distilled alcohol beverages. It is also a product of microbial (gut) metabolism of anthocyanins and other polyphenols that have been consumed (in fruits and alcoholic beverages - PMID: 18767860 ). Research suggests that phenolics from wine may play a positive role against oxidation of low-density lipoprotein (LDL), which is a key step in the development of atherosclerosis. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. (PMID 15545043 ).
Structure
Thumb
Synonyms
ValueSource
Cedar acidChEBI
Gallic acid 3,5-dimethyl etherChEBI
SyringateGenerator
Gallate 3,5-dimethyl etherGenerator
3,5-Dimethoxy-4-hydroxybenzoateHMDB
3,5-Dimethoxy-4-hydroxybenzoic acidHMDB
3,5-Dimethoxybenzoyl hydrazineHMDB
3,5-Dimethyl-4-hydroxybenzoateHMDB
3,5-Dimethyl-4-hydroxybenzoic acidHMDB
4-Hydroxy-3,5-dimethylbenzoateHMDB
4-Hydroxy-3,5-dimethylbenzoic acidHMDB
SyringlicacidHMDB
Syringic acid cu (+2) salt (1:1)MeSH
Chemical FormulaC9H10O5
Average Molecular Weight198.174
Monoisotopic Molecular Weight198.052823422
IUPAC Name4-hydroxy-3,5-dimethoxybenzoic acid
Traditional Namesyringic acid
CAS Registry Number530-57-4
SMILES
COC1=CC(=CC(OC)=C1O)C(O)=O
InChI Identifier
InChI=1S/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12)
InChI KeyJMSVCTWVEWCHDZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gallic acid and derivatives. These are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentGallic acid and derivatives
Alternative Parents
Substituents
  • Gallic acid or derivatives
  • M-methoxybenzoic acid or derivatives
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Phenol
  • 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 Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
  • Microbial
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point206 - 209 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.04HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.71 mg/mLALOGPS
logP1.55ALOGPS
logP1.01ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.22 m3·mol-1ChemAxon
Polarizability18.77 Å3ChemAxon
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-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-052f-0900000000-14ec0ce09465c51ccc37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-004l-9800000000-9765822b3b1e2ec9d9deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-004j-9100000000-8d01bd5b04dae916e4aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-0a0256c7bc33c2d88a4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0fka-0900000000-254d42fb132329839152View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-1900000000-304c5119148e7f55f4d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00b9-9500000000-49a00cfe65ce9eabeb4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004r-9000000000-80475497b3098dd00777View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-01d0ea76c3ba0db41782View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0900000000-87ada1ca48a49d9677ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-019cee52e59a254e3fcfView in MoNA
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)splash10-0002-5900000000-0b6163fb3f78b99ad5ddView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected and Quantified2.119 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified3.885 +/- 1.867 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified9.285 +/- 5.601 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    SalivaDetected and Quantified1.57 +/- 0.123 uMAdult (>18 years old)Both
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified1.59 +/- 0.118 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified1.62 +/- 0.105 uMAdult (>18 years old)Both
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified1.71 +/- 0.0913 uMAdult (>18 years old)Male
    Normal
      • Sugimoto et al. (...
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 420 details
    UrineDetected and Quantified0.9 +/- 0.2 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
    UrineDetected and Quantified1.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound ID420
    Phenol Explorer Metabolite ID420
    FoodDB IDFDB000514
    KNApSAcK IDC00002674
    Chemspider ID10289
    KEGG Compound IDC10833
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0002085
    METLIN ID2256
    PubChem Compound10742
    PDB IDNot Available
    ChEBI ID454990
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Kalkan Yildirim H, Delen Akcay Y, Guvenc U, Yildirim Sozmen E: Protection capacity against low-density lipoprotein oxidation and antioxidant potential of some organic and non-organic wines. Int J Food Sci Nutr. 2004 Aug;55(5):351-62. [PubMed:15545043 ]
    2. Forester SC, Waterhouse AL: Identification of Cabernet Sauvignon anthocyanin gut microflora metabolites. J Agric Food Chem. 2008 Oct 8;56(19):9299-304. doi: 10.1021/jf801309n. Epub 2008 Sep 4. [PubMed:18767860 ]