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Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2024-04-19 10:04:04 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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abutilon indicumPlant
Acacia mearnsiiLOTUS Database
Aegiceras corniculatumLOTUS Database
Aframomum giganteumPlant
African marigoldLOTUS Database
Agrostophyllum callosumLOTUS Database
Alcea roseaLOTUS Database
Alnus japonicaLOTUS Database
Althaea nudifloraPlant
Althaea officinalisPlant
Althaea roseaPlant
Anethum foeniculumPlant
Anethum graveolensFooDB
Anisophyllea dichostyla-
Annona cherimolaLOTUS Database
Apis ceranaLOTUS Database
Arabidopsis thalianaPlant
Arachis hypogaeaFooDB
Aristolochia heterophyllaLOTUS Database
Aristolochia heterophylla HemslPlant
Artemisia dracunculusFooDB
Avena sativaLOTUS Database
Avena sativa L.FooDB
Balanites aegyptiacaLOTUS Database
Beta vulgarisLOTUS Database
Beta vulgaris ssp. ciclaFooDB
Betula pendulaLOTUS Database
Brassica napusLOTUS Database
Brassica napus var. napusFooDB
Brassica oleracea var. botrytisFooDB
Brettanomyces anomalusLOTUS Database
Cajanus cajanFooDB
Calendula officinalisPlant
Callicarpa integerrimaPlant
Campanula persicifoliaLOTUS Database
Caraipa densifoliaPlant
Casuarina equisetifoliaLOTUS Database
Catalpa ovataPlant
Ceanothus americanusPlant
Ceratostigma willmottianumPlant
Cestrum parquiLOTUS Database
Chamomilla rectitaPlant
Cheniella glaucaLOTUS Database
Cicer arietinumFooDB
Cichorium intybusFooDB
Cinnamomum subaveniumPlant
Cinnamomum tenuifoliumLOTUS Database
Cinnamomum verumFooDB
Citrus sinensisLOTUS Database
Citrus spp.Plant
Clausena excavataLOTUS Database
Cleidion spiciflorum (Burm. f.) Merr.Plant
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colubrina faralaotra subsp.trichocarpa.Plant
Conyza bonariensisLOTUS Database
Conyza candensisPlant
Coriandrum sativum L.FooDB
Corymbia citriodoraLOTUS Database
Crataegus monogynaLOTUS Database
Crocus sativusPlant
CucurbitaFooDB
Cuminum cyminumFooDB
Curculigo orchioidesPlant
Curcuma longaFooDB
Cynanchum vincetoxicumLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Diospyros erianthaPlant
Diospyros kakiLOTUS Database
Diospyros lotusLOTUS Database
Duhaldea cappaLOTUS Database
Elettaria cardamomumFooDB
Eleusine coracanaPlant
Eleutherococcus senticosusLOTUS Database
Erigeron canadensisPlant
Ervatamia coronariaLOTUS Database
Eschenbachia bliniiLOTUS Database
Euphorbia heteradenaLOTUS Database
Eurycoma longifoliaLOTUS Database
Fagopyrum esculentumFooDB
Falcaria vulgarisPlant
Fibraurea tinctoriaLOTUS Database
Ficus caricaFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Galinsoga quadriradiataLOTUS Database
Gardenia sootepensisLOTUS Database
Geranium platyanthumLOTUS Database
Gliricidia sepiumLOTUS Database
Glycine maxFooDB
Gnetum parvifoliumLOTUS Database
Gossypium hirsutumLOTUS Database
Haematoxylum campechianumLOTUS Database
Halocharis hispidaLOTUS Database
Helianthus annuus L.FooDB
Hibiscus taiwanensisPlant
Homo sapiensLOTUS Database
Homo sapiens (Urine)Animalia
Hordeum vulgareFooDB
Hornstedtia reticulataLOTUS Database
Humulus lupulusPlant
Hyssopus officinalis L.FooDB
Impatiens balsaminaPlant
Inonotus obliquusFungi
Isatis tinctoriaPlant
Juglans cinereaLOTUS Database
Juglans nigra L.FooDB
Juglans regiaFooDB
Kalanchoe pinnataPlant
Lentinus edodes-
Leonurus japonicusLOTUS Database
Lepisorus contortusLOTUS Database
Limonium gmeliniiLOTUS Database
Limonium wrightiiLOTUS Database
Lindera glaucaLOTUS Database
Liriodendron tulipiferaLOTUS Database
Lonicera hypoleucaLOTUS Database
Lycopus europaeusLOTUS Database
Magnolia grandifloraLOTUS Database
Malus pumilaFooDB
Mangifera indicaPlant
Maranta arundinaceaFooDB
Matricaria chamomillaPlant
Matricaria recutitaFooDB
Melicope semecarpifoliaPlant
Melissa officinalis L.FooDB
Mentha spicataFooDB
Menyanthes trifoliataLOTUS Database
Mespilus germanicaPlant
Michelia compressaLOTUS Database
Microtropis fokienensisPlant
Millettia leucanthaLOTUS Database
Moringa oleiferaPlant
Moringa peregrinaPlant
Moringa stenopetalaPlant
Mosla chinensisLOTUS Database
Mucuna birdwoodianaLOTUS Database
Muntingia calaburaLOTUS Database
Myristica fragransFooDB
Neolitsea hiiranensisLOTUS Database
Ocimum basilicumFooDB
Oenothera biennisFooDB
Oenothera elataLOTUS Database
Olea europaeaFooDB
Ophiocordyceps sinensisLOTUS Database
Origanum majoranaFooDB
Origanum vulgareFooDB
Oryza sativaFooDB
Paeonia obovataLOTUS Database
Panicum milliaceumPlant
Pentanema britannicumPlant
Peperomia duclouxii C. DC.Plant
Peperomia heyneanaLOTUS Database
Persea americanaLOTUS Database
Persicaria lapathifoliaLOTUS Database
Petroselinum crispumFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phellinus igniariusFungi
Phlomoides hamosaLOTUS Database
Phoenix dactyliferaFooDB
Pimpinella anisumFooDB
Pinus sibiricaPlant
Pisum sativumFooDB
Pittosporum illicioidesLOTUS Database
Plantago lanceolataPlant
Plantago majorPlant
Plantago mediaPlant
Populus euphraticaLOTUS Database
Populus lasiocarpaLOTUS Database
Posidonia oceanicaPlant
Prunus domesticaLOTUS Database
Punica granatumPlant
Pyrus communisFooDB
Quercus infectoriaPlant
Quercus petraeaLOTUS Database
Quercus roburLOTUS Database
Rhaponticum carthamoidesPlant
Rhinacanthus nasutusLOTUS Database
Rhododendron dauricumPlant
Rhododendron micranthumPlant
Rhododendron mucronatumPlant
Rhododendron mucronulatumPlant
Ribes nigrumFooDB
Rohdea chinensisPlant
Rorippa indicaLOTUS Database
Rorippa sylvestrisLOTUS Database
Rubia yunnanensisPlant
Rubus idaeusFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Santalum albumLOTUS Database
Sarcandra glabraLOTUS Database
Sargentodoxa cuneataLOTUS Database
Satureja hortensis L.Plant
Satureja subspicataPlant
Scolochloa festucaceaLOTUS Database
Scrophularia frutescensPlant
Scrophularis sambucifolia-
Secale cerealeFooDB
Secamone afzeliiLOTUS Database
Sida acutaLOTUS Database
Silphium perfoliatumLOTUS Database
Siphoneugena densifloraLOTUS Database
Smilax glabraPlant
Solanum lycopersicum var. lycopersicumFooDB
Solidago canadensisLOTUS Database
Solori scandensPlant
Sorghum bicolorPlant
Spiraea formosanaPlant
Stenoloma chusanum-
Strobilanthes crispusPlant
Synechococcus elongatusLOTUS Database
Synsepalum dulcificumLOTUS Database
Syzygium aromaticumFooDB
Tagetes minutaLOTUS Database
Talipariti tiliaceumPlant
Tamarix gallicaPlant
Tamarix hispidaLOTUS Database
Taraxacum formosanumPlant
Taxus baccataPlant
Theobroma cacaoFooDB
Thymus capitatusPlant
Thymus vulgarisFooDB
Tragopogon orientalisLOTUS Database
Trichilia emeticaPlant
Triticum aestivumFooDB
Triticum durumFooDB
Triticum turgidumLOTUS Database
Vaccinium macrocarponLOTUS Database
Vaccinium myrtillusFooDB
Verbesina myriocephalaLOTUS Database
Veronica spicataPlant
Vicia fabaFooDB
Vigna radiataFooDB
Vigna unguiculataFooDB
Vincetoxicum atratumLOTUS Database
Visnea mocaneraLOTUS Database
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Withania somniferaPlant
Zanthoxylum ailanthoidesLOTUS Database
Zanthoxylum leprieuriiLOTUS Database
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 ]