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Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2020-09-11 01:33:56 UTC
NP-MRD IDNP0000022
Secondary Accession NumbersNone
Natural Product 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. A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. 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 rosemaries, romaine lettuces, and grape wines. Syringic acid has also been detected, but not quantified in, several different foods, such as broad beans, sorghums, garden tomato (var.), Teffs, and parsley. This could make syringic acid a potential biomarker for the consumption of these foods.
Structure
Thumb
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
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesPlantae; Eubacteria
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
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
User Submitted Data
Not Available
HMDB IDHMDB0002085
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
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 ]