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
DescriptionCaffeic acid is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food. (PMID:16870009) [HMDB]. Caffeic acid is found in many foods, some of which are cardoon, coriander, common persimmon, and irish moss.
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
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 Key
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
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).