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Record Information
Version4.0
Creation Date2006-05-22 14:17:35 UTC
Update Date2017-10-23 19:03:56 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
Disposition

Biological Location:

  Biofluid and excreta:

Source:

  Biological:

    Plant:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.22 m³·mol⁻¹ChemAxon
Polarizability18.77 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, Positivesplash10-0f8a-0900000000-7b568e18ffde6ab04131View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-8095000000-575a6ec78ed017731cc6View in MoNA
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 , negativesplash10-0002-0900000000-0a0256c7bc33c2d88a4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fka-0900000000-254d42fb132329839152View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-01d0ea76c3ba0db41782View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-9500000000-49a00cfe65ce9eabeb4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-9000000000-80475497b3098dd00777View 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, Positivesplash10-0002-0900000000-6ce63e339a947f904864View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900000000-a397243a2d8f8f9e501dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-2900000000-d3241b91846d43efb768View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e699dd409e203e12842fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uds-0900000000-b5bde1ce65999b3cf7deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fa9-2900000000-87c04717df825474388dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-5900000000-0b6163fb3f78b99ad5ddView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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
    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 ]

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    Reactions
    Syringic acid → 6-(4-carboxy-2,6-dimethoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
    Syringic acid → 3,4,5-trihydroxy-6-(4-hydroxy-3,5-dimethoxybenzoyloxy)oxane-2-carboxylic aciddetails
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
    Gene Name:
    GLYAT
    Uniprot ID:
    Q6IB77
    Molecular weight:
    18506.33
    Reactions
    Syringic acid → 2-{[hydroxy(4-hydroxy-3,5-dimethoxyphenyl)methylidene]amino}acetic aciddetails
    General function:
    sulfotransferase activity
    Specific function:
    Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
    Gene Name:
    SULT1A3
    Uniprot ID:
    P0DMM9
    Molecular weight:
    34195.96
    Reactions
    Syringic acid → 3,5-dimethoxy-4-(sulfooxy)benzoic aciddetails