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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2020-02-26 21:23:48 UTC
HMDB IDHMDB0002085
Secondary Accession Numbers
  • HMDB02085
Metabolite Identification
Common NameSyringic acid
DescriptionSyringic acid, also known as syringate or cedar acid, 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. Syringic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Syringic acid is found, on average, in the highest concentration within a few different foods, such as common walnuts, swiss chards, and olives and in a lower concentration in apples, tarragons, and peanuts. Syringic acid has also been detected, but not quantified in, several different foods, such as sweet marjorams, silver lindens, bulgurs, annual wild rices, and barley. This could make syringic acid a potential biomarker for the consumption of these foods. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. 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 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 ). Syringic acid is also a microbial metabolite that can be found in Bifidobacterium (PMID: 24958563 ).
Structure
Data?1582752228
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8a-0900000000-7b568e18ffde6ab04131Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-8095000000-575a6ec78ed017731cc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-052f-0900000000-14ec0ce09465c51ccc37Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-004l-9800000000-9765822b3b1e2ec9d9deSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-004j-9100000000-8d01bd5b04dae916e4aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-0a0256c7bc33c2d88a4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0fka-0900000000-254d42fb132329839152Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-1900000000-304c5119148e7f55f4d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00b9-9500000000-49a00cfe65ce9eabeb4cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004r-9000000000-80475497b3098dd00777Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-0a0256c7bc33c2d88a4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fka-0900000000-254d42fb132329839152Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-01d0ea76c3ba0db41782Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-9500000000-49a00cfe65ce9eabeb4cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-9000000000-80475497b3098dd00777Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0900000000-87ada1ca48a49d9677ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-019cee52e59a254e3fcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-6ce63e339a947f904864Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900000000-a397243a2d8f8f9e501dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-2900000000-d3241b91846d43efb768Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e699dd409e203e12842fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uds-0900000000-b5bde1ce65999b3cf7deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fa9-2900000000-87c04717df825474388dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0002-5900000000-0b6163fb3f78b99ad5ddSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedNot 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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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