Record Information
Version1.0
Creation date2010-04-08 22:13:55 UTC
Update date2018-01-23 20:00:17 UTC
Primary IDFDB018772
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaftaric acid
DescriptionCaftaric acid is the main hydroxycinnamate in both red and white wines produced from Vitis vinifera and well as Concord grape juice, which is a product of grapes of Vitis lambrusca. Caftaric acid is found in many foods, some of which are fox grape, grape wine, sherry, and vinegar.
CAS Number67879-58-7
Structure
Thumb
Synonyms
SynonymSource
Monocaffeoyl(-)-tartarateGenerator
Caffeoyltartaric aciddb_source
Caftaric aciddb_source
Monocaffeoyltartaric aciddb_source
Monocaffeyltartaric acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP1.68ALOGPS
logP0.6ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity69.74 m³·mol⁻¹ChemAxon
Polarizability28.16 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC13H12O9
IUPAC name2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
InChI IdentifierInChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+
InChI KeySWGKAHCIOQPKFW-DUXPYHPUSA-N
Isomeric SMILES[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OC(C(O)C(O)=O)C(O)=O
Average Molecular Weight312.229
Monoisotopic Molecular Weight312.048131982
Classification
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Tricarboxylic acid or derivatives
  • Styrene
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Sugar acid
  • Fatty acid ester
  • Phenol
  • Beta-hydroxy acid
  • Fatty acyl
  • Benzenoid
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 50.01%; H 3.87%; O 46.12%DFC
Melting PointMp 125° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -28.2DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9840000000-cd512aa4b5b39796cfc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0973000000-1a96d8a708695d13762eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gr-2940000000-a24c1bc2573e378ccd7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-4900000000-55b90a17ab1875f9bb88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0409-3982000000-aabe941096f73c4a6cd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02dr-3940000000-9757ec14c725e63e898eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03mi-3910000000-aec72816b3809d559efeView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6440397
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID460
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBTJ82-E:LMQ41-J
EAFUS IDNot Available
Dr. Duke IDMONOCAFFEOYLTARTARIC-ACID|TRANS-CAFTARIC-ACID|CAFFEOYLTARTARIC-ACID|CAFTARIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1454661
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti otitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
bacteristat33282 A substance that kills or slows the growth of bacteria.DUKE
hyaluronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.