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Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2022-04-04 17:30:54 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
3,5-Dimethoxygallic acidHMDB
3,5-O-Dimethylgallic acidHMDB
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
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-04-04View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-04-04View Spectrum
Species
Species of Origin
Species NameSourceReference
Abutilon indicumPlant
Aframomum giganteumPlant
Althaea nudifloraPlant
Althaea officinalisPlant
Althaea roseaPlant
Anethum foeniculumPlant
Anethum graveolensFooDB
Anisophyllea dichostyla-
Arabidopsis thalianaPlant
Arachis hypogaeaFooDB
Aristolochia heterophylla HemslPlant
Artemisia dracunculusFooDB
Avena sativa L.FooDB
Beta vulgaris ssp. ciclaFooDB
Brassica napus var. napusFooDB
Brassica oleracea var. botrytisFooDB
Cajanus cajanFooDB
Calendula officinalisPlant
Callicarpa integerrimaPlant
Caraipa densifoliaPlant
Catalpa ovataPlant
Ceanothus americanusPlant
Ceratostigma willmottianumPlant
Chamomilla rectitaPlant
Cicer arietinumFooDB
Cichorium intybusFooDB
Cinnamomum subaveniumPlant
Cinnamomum verumFooDB
Citrus spp.Plant
Cleidion spiciflorum (Burm. f.) Merr.Plant
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colubrina faralaotra subsp.trichocarpa.Plant
Conyza candensisPlant
Coriandrum sativum L.FooDB
Crocus sativusPlant
CucurbitaFooDB
Cuminum cyminumFooDB
Curculigo orchioidesPlant
Curcuma longaFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Diospyros erianthaPlant
Elettaria cardamomumFooDB
Eleusine coracanaPlant
Erigeron canadensisPlant
Fagopyrum esculentumFooDB
Falcaria vulgarisPlant
Ficus caricaFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Glycine maxFooDB
Helianthus annuus L.FooDB
Hibiscus taiwanensisPlant
Homo sapiens (Urine)Animalia
Hordeum vulgareFooDB
Humulus lupulusPlant
Hyssopus officinalis L.FooDB
Impatiens balsaminaPlant
Inonotus obliquusFungi
Isatis tinctoriaPlant
Juglans nigra L.FooDB
Juglans regiaFooDB
Kalanchoe pinnataPlant
Lentinus edodes-
Malus pumilaFooDB
Mangifera indicaPlant
Maranta arundinaceaFooDB
Matricaria chamomillaPlant
Matricaria recutitaFooDB
Melicope semecarpifoliaPlant
Melissa officinalis L.FooDB
Mentha spicataFooDB
Mespilus germanicaPlant
Microtropis fokienensisPlant
Moringa oleiferaPlant
Moringa peregrinaPlant
Moringa stenopetalaPlant
Myristica fragransFooDB
Ocimum basilicumFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Origanum majoranaFooDB
Origanum vulgareFooDB
Oryza sativaFooDB
Panicum milliaceumPlant
Pentanema britannicumPlant
Peperomia duclouxii C. DC.Plant
Petroselinum crispumFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phellinus igniariusFungi
Phoenix dactyliferaFooDB
Pimpinella anisumFooDB
Pinus sibiricaPlant
Pisum sativumFooDB
Plantago lanceolataPlant
Plantago majorPlant
Plantago mediaPlant
Posidonia oceanicaPlant
Punica granatumPlant
Pyrus communisFooDB
Quercus infectoriaPlant
Rhaponticum carthamoidesPlant
Rhododendron dauricumPlant
Rhododendron micranthumPlant
Rhododendron mucronatumPlant
Rhododendron mucronulatumPlant
Ribes nigrumFooDB
Rohdea chinensisPlant
Rubia yunnanensisPlant
Rubus idaeusFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Satureja hortensis L.Plant
Satureja subspicataPlant
Scrophularia frutescensPlant
Scrophularis sambucifolia-
Secale cerealeFooDB
Smilax glabraPlant
Solanum lycopersicum var. lycopersicumFooDB
Solori scandensPlant
Sorghum bicolorPlant
Spiraea formosanaPlant
Stenoloma chusanum-
Strobilanthes crispusPlant
Syzygium aromaticumFooDB
Talipariti tiliaceumPlant
Tamarix gallicaPlant
Taraxacum formosanumPlant
Taxus baccataPlant
Theobroma cacaoFooDB
Thymus capitatusPlant
Thymus vulgarisFooDB
Trichilia emeticaPlant
Triticum aestivumFooDB
Triticum durumFooDB
Vaccinium myrtillusFooDB
Veronica spicataPlant
Vicia fabaFooDB
Vigna radiataFooDB
Vigna unguiculataFooDB
Vitis vinifera L.FooDB
Withania somniferaPlant
Zanthoxylum simulansPlant
Zea mays L.FooDB
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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (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
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 IDrw1285301
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 ]
  6. Guzelad O, Ozkan A, Parlak H, Sinen O, Afsar E, Ogut E, Yildirim FB, Bulbul M, Agar A, Aslan M: Protective mechanism of Syringic acid in an experimental model of Parkinson's disease. Metab Brain Dis. 2021 Jun;36(5):1003-1014. doi: 10.1007/s11011-021-00704-9. Epub 2021 Mar 5. [PubMed:33666819 ]