Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2018-05-28 22:40:32 UTC
Primary IDFDB002427
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRosmarinic acid
DescriptionIsolated from rosemary, mint, sage, thyme, lemon balm and other plants Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. It is a red-orange powder that is slightly soluble in water, but well soluble is most organic solvents. Rosmarinic acid is one of the polyphenolic substances contained in culinary herbs such as perilla (Perilla frutescens L.), rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). These herbs are commonly grown in the garden as kitchen herbs, and while used to add flavor in cooking, are also known to have several potent physiological effects. (PMID: 12482446, 15120569); Rosmarinic acid, C18H16O8, is a natural polyphenol antioxidant carboxylic acid found in many Lamiaceae herbs used commonly as culinary herbs such as lemon balm, rosemary, oregano, sage, thyme and peppermint. Chemically, rosmarinic acid is an ester of caffeic acid with 3,4-dihydroxyphenyl lactic acid. It is a red-orange powder that is slightly soluble in water, but well soluble in most organic solvents.
CAS Number537-15-5
Structure
Thumb
Synonyms
SynonymSource
alpha-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoic acidChEBI
R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionic acidChEBI
a-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoateGenerator
a-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoic acidGenerator
alpha-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoateGenerator
α-(((3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoateGenerator
α-(((3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoic acidGenerator
RosmarinateGenerator
R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionateGenerator
Rosemarinic acidMeSH
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactateGenerator
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactic acidChEBI
Labiatenic aciddb_source
Rosemary acidbiospider
Rosmarinic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP2.57ALOGPS
logP3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.95 m³·mol⁻¹ChemAxon
Polarizability34.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H16O8
IUPAC name3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
InChI IdentifierInChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+
InChI KeyDOUMFZQKYFQNTF-ZZXKWVIFSA-N
Isomeric SMILES[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OC(CC1=CC(O)=C(O)C=C1)C(O)=O
Average Molecular Weight360.3148
Monoisotopic Molecular Weight360.084517488
Classification
DescriptionThis compound 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
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • 3-phenylpropanoic-acid
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 PointMp 204° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +145DFC
Spectroscopic UV Data329 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a59-6429037000-febdf15ccc07a12300c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-2901000000-a7651199b7749acc2b9fView in MoNA
ChemSpider ID4445104
ChEMBL IDCHEMBL324842
KEGG Compound IDC01850
Pubchem Compound ID5281792
Pubchem Substance IDNot Available
ChEBI ID17226
Phenol-Explorer ID461
DrugBank IDNot Available
HMDB IDHMDB03572
CRC / DFC (Dictionary of Food Compounds) IDBKF39-R:CLS91-G
EAFUS IDNot Available
Dr. Duke IDROSMARINIC-ACID
BIGG IDNot Available
KNApSAcK IDC00002770
HET IDROA
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRosmarinic acid
Phenol-Explorer Metabolite ID461
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
beta inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
adenylate-cyclase 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
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
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti anaphylactic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti atherosclerotic38070 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 coagulant50249 An agent that prevents blood clotting.DUKE
anti complementaryDUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti gonadotropicDUKE
anti hemolytic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.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 HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
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 integrase23924 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 leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti lipoperoxidantDUKE
anti mutagenicDUKE
anti nephritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
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 plaqueDUKE
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 proteolyticDUKE
anti pulmonoticDUKE
anti radicularDUKE
anti shockDUKE
anti thyreotropicDUKE
anti thyroidDUKE
anti uremicDUKE
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
apoptoticDUKE
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
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
deiodinase 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
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.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
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
neuroprotective63726 Any compound that can be used for the treatment of neurodegenerative disorders.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
radioprotective35232 Any pharmaceutical compound containing a radioisotope.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.