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Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2021-06-29 00:47:21 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. 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
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 Mass198.1740 Da
Monoisotopic Mass198.05282 Da
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 TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, DMSO, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Plantae
  • 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
    External Links
    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
    Good Scents IDNot Available
    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 ]
    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 ]
    4. Kusano R, Ogawa S, Matsuo Y, Tanaka T, Yazaki Y, Kouno I: alpha-Amylase and lipase inhibitory activity and structural characterization of acacia bark proanthocyanidins. J Nat Prod. 2011 Feb 25;74(2):119-28. doi: 10.1021/np100372t. Epub 2010 Dec 30. [PubMed:21192716 ]
    5. Yang JH, Kondratyuk TP, Jermihov KC, Marler LE, Qiu X, Choi Y, Cao H, Yu R, Sturdy M, Huang R, Liu Y, Wang LQ, Mesecar AD, van Breemen RB, Pezzuto JM, Fong HH, Chen YG, Zhang HJ: Bioactive compounds from the fern Lepisorus contortus. J Nat Prod. 2011 Feb 25;74(2):129-36. doi: 10.1021/np100373f. Epub 2011 Jan 24. [PubMed:21261296 ]