Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2018-01-23 18:52:50 UTC
Primary IDFDB002558
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaffeic acid
Descriptiontrans-caffeic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. trans-caffeic acid is a drug. trans-caffeic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The trans-isomer of caffeic acid.
CAS Number331-39-5
Structure
Thumb
Synonyms
SynonymSource
3,4-Dihydroxy-trans-cinnamateChEBI
3,4-Dihydroxycinnamic acidChEBI
CAFFEIC ACIDChEBI
trans-CaffeateChEBI
3,4-Dihydroxy-trans-cinnamic acidGenerator
3,4-DihydroxycinnamateGenerator
CAFFEateGenerator
trans-Caffeic acidGenerator
Caffeic acid, monosodium saltMeSH
Caffeic acid, (e)-isomerMeSH
Sodium caffeateMeSH
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(E)-3,4-Dihydroxycinnamic acidHMDB
(E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(E)-3-(3,4-Dihydroxyphenyl)acrylic acidHMDB
(E)-Caffeic acidHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
3-(3,4-Dihydroxyphenyl)propenoic acidHMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzeneHMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzeneHMDB
4-(2’-Carboxyvinyl)-1,2-dihydroxybenzeneHMDB
DHCAHMDB
trans-3,4-Dihydroxycinnamic acidHMDB
3,4-DihydroxybenzeneacrylateHMDB
3,4-Dihydroxycinnamic acid, 8CIdb_source
CaffeateChEBI
Caffeic aciddb_source
Caffeic acid pureHMDB
CaffeicacidHMDB
cis-CaffeateGenerator
cis-Caffeic acidChEBI
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP1.67ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.64ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability17.34 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H8O4
IUPAC name(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChI KeyQAIPRVGONGVQAS-DUXPYHPUSA-N
Isomeric SMILESOC(=O)\C=C\C1=CC(O)=C(O)C=C1
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
Classification
Description belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 60.00%; H 4.48%; O 35.52%DFC
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data320 () (MeOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1593000000-b24e97b50ed1f50252f3JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9800000000-bae43e98e22babcbf5a7JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9600000000-6140146b8e32bda5e3c9JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0593000000-16610dfa8ac4ac67a4c2JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1593000000-b24e97b50ed1f50252f3JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0592000000-1bb03bc99be6718d247eJSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-6a963e50b910f05b6825JSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00e9-5039000000-d55c6a31e04536d33b58JSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-03di-0900000000-f31bbdf32d6b72a381e7JSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-3f202efcd71f15f33da9JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-1900000000-c772ffdf277b1e52c37aJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdr-9700000000-5a4b1d97b748046bf13aJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f196cd5c6ab6f34ffec7JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-359be86d681a33921515JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0913-2900000000-8a1b926d906ffae34e16JSpectraViewer
    ChemSpider ID1266077
    ChEMBL IDCHEMBL1320034
    KEGG Compound IDC01481
    Pubchem Compound ID1549111
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID457
    DrugBank IDNot Available
    HMDB IDHMDB01964
    CRC / DFC (Dictionary of Food Compounds) IDCMK09-G:CMK09-G
    EAFUS IDNot Available
    Dr. Duke IDCIS-CAFFEIC-ACID|CAFFEIC-ACID|3,4-DIHYDROXYCINNAMIC-ACID
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDCaffeic_acid
    Phenol-Explorer Metabolite ID457
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
    allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
    analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
    anti adenoviral22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti aggregantDUKE
    anti aging52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti atherogenic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti edemicDUKE
    anti elastase23924 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
    anti escherichicDUKE
    anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti gonadotropicDUKE
    anti hemolytic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
    anti hepatoadenomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
    anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
    anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti hypercholesterolemicDUKE
    anti hyperthyroid52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
    anti legionella33282 A substance that kills or slows the growth of bacteria.DUKE
    anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
    anti melanogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti mutagenicDUKE
    anti nitrosaminicDUKE
    anti ophidicDUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti peroxidantDUKE
    anti proliferantDUKE
    anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
    anti radicularDUKE
    anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
    anti stomatiticDUKE
    anti sunburn52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti thiaminDUKE
    anti thyroidDUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti ulcerogenic49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
    anti vaccinia22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
    anxiolytic35474 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.DUKE
    calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
    chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    cholagogueDUKE
    cholereticDUKE
    clastogenicDUKE
    central nervous system active35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
    collagen-sparingDUKE
    cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
    cytoprotectiveDUKE
    cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
    diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
    DNA-activeDUKE
    DNA-protectiveDUKE
    fungicide24127 A substance used to destroy fungal pests.DUKE
    hepatocarcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
    hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
    hepatotropicDUKE
    histamine inhibitor37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
    immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
    insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
    leukotriene inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
    lyase 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
    metal chelator38161 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.DUKE
    ornithine-decarboxylase 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
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    prooxidantDUKE
    prostaglandigenicDUKE
    sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
    sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    tumorigenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
    vulnerary73336 A drug used in treating and healing of wounds.DUKE
    xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— 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.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).