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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2019-03-20 17:19:04 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 ). Syringic acid is also a microbial metabolite that can be found in Bifidobacterium (PMID: 24958563 ).
Structure
Data?1547234198
Synonyms
ValueSource
Cedar acidChEBI
Gallic acid 3,5-dimethyl etherChEBI
SyringateKegg
4-Hydroxy-3,5-dimethoxybenzoateKegg
Gallate 3,5-dimethyl etherGenerator
4-Hydroxy-3,5-dimethoxybenzoic acidGenerator
Syringic acid cu (+2) salt (1:1)HMDB
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
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
Description belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and 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

Route of exposure:

Source:

Biological location:

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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8a-0900000000-7b568e18ffde6ab04131JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-8095000000-575a6ec78ed017731cc6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-052f-0900000000-14ec0ce09465c51ccc37JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-004l-9800000000-9765822b3b1e2ec9d9deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-004j-9100000000-8d01bd5b04dae916e4aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-0a0256c7bc33c2d88a4eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0fka-0900000000-254d42fb132329839152JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-1900000000-304c5119148e7f55f4d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00b9-9500000000-49a00cfe65ce9eabeb4cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004r-9000000000-80475497b3098dd00777JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-0a0256c7bc33c2d88a4eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fka-0900000000-254d42fb132329839152JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-01d0ea76c3ba0db41782JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-9500000000-49a00cfe65ce9eabeb4cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-9000000000-80475497b3098dd00777JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0900000000-87ada1ca48a49d9677ddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-019cee52e59a254e3fcfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-6ce63e339a947f904864JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900000000-a397243a2d8f8f9e501dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-2900000000-d3241b91846d43efb768JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e699dd409e203e12842fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uds-0900000000-b5bde1ce65999b3cf7deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fa9-2900000000-87c04717df825474388dJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-5900000000-0b6163fb3f78b99ad5ddJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0-7.1 uMAdult (>18 years old)MaleNormal details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified2.119 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified3.885 +/- 1.867 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified9.285 +/- 5.601 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified2.155 (0.121-6.0704) nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>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
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    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 References
    Colorectal cancer
    1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound ID420
    FoodDB IDFDB000514
    KNApSAcK IDC00002674
    Chemspider ID10289
    KEGG Compound IDC10833
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkSyringic_acid
    METLIN ID2256
    PubChem Compound10742
    PDB IDNot Available
    ChEBI ID68329
    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 ]
    3. Boto-Ordonez M, Urpi-Sarda M, Queipo-Ortuno MI, Tulipani S, Tinahones FJ, Andres-Lacueva C: High levels of Bifidobacteria are associated with increased levels of anthocyanin microbial metabolites: a randomized clinical trial. Food Funct. 2014 Aug;5(8):1932-8. doi: 10.1039/c4fo00029c. [PubMed:24958563 ]

    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