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Record Information
Version3.6
Creation Date2006-08-13 00:44:12 UTC
Update Date2017-08-16 04:10:46 UTC
HMDB IDHMDB0003572
Secondary Accession Numbers
  • HMDB02887
  • HMDB03572
Metabolite Identification
Common NameRosmarinic acid
DescriptionRosmarinic 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 ).
Structure
Thumb
Synonyms
ValueSource
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactic acidChEBI
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactateGenerator
RosmarinateGenerator
Rosemary acidHMDB
Rosmarinic acid, (R-(e))-isomerMeSH
Chemical FormulaC18H16O8
Average Molecular Weight360.3148
Monoisotopic Molecular Weight360.084517488
IUPAC Name(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
Traditional Namerosemary acid
CAS Registry Number537-15-5
SMILES
OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=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+/t16-/m1/s1
InChI KeyDOUMFZQKYFQNTF-WUTVXBCWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCinnamic 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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.041 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.95 m3·mol-1ChemAxon
Polarizability34.55 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00kb-1889000000-a18403fdf27acdd9420aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0901000000-f29409b402b063dcbebdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0bt9-0907000100-ececf6d2ede2e8193b9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03e9-0900000000-14bb8ce94558a85b706cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0902000000-f3cc2fa86fc00ea8e474View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-0dac983721970230a210View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0439000000-38b13aa5bfab28c4d0c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-383db44d2370c9662666View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-008i-0679000000-629ad81e5a4aa4a45cd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-f099de2a6e6ab011d21bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-f099de2a6e6ab011d21bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-529a6653ec4eebdd8eebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-529a6653ec4eebdd8eebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 461 details
BloodDetected and Quantified1.38 (0.0055 - 5.55) uMAdult (>18 years old)BothNormal details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 461 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID461
Phenol Explorer Metabolite ID461
FoodDB IDFDB002427
KNApSAcK IDC00002770
Chemspider ID4445104
KEGG Compound IDC01850
BioCyc IDCPD-7018
BiGG IDNot Available
Wikipedia LinkRosmarinic acid
NuGOwiki LinkHMDB0003572
METLIN ID6960
PubChem Compound5281792
PDB IDROA
ChEBI ID50371
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Li X, Yu C, Cai Y, Liu G, Jia J, Wang Y: Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):41-7. Epub 2005 Apr 19. [PubMed:15866491 ]
  2. Sahu A, Rawal N, Pangburn MK: Inhibition of complement by covalent attachment of rosmarinic acid to activated C3b. Biochem Pharmacol. 1999 Jun 15;57(12):1439-46. [PubMed:10353266 ]
  3. Lee J, Jung E, Kim Y, Lee J, Park J, Hong S, Hyun CG, Park D, Kim YS: Rosmarinic acid as a downstream inhibitor of IKK-beta in TNF-alpha-induced upregulation of CCL11 and CCR3. Br J Pharmacol. 2006 Jun;148(3):366-75. [PubMed:16604092 ]
  4. Petersen M, Simmonds MS: Rosmarinic acid. Phytochemistry. 2003 Jan;62(2):121-5. [PubMed:12482446 ]
  5. Baba S, Osakabe N, Natsume M, Terao J: Orally administered rosmarinic acid is present as the conjugated and/or methylated forms in plasma, and is degraded and metabolized to conjugated forms of caffeic acid, ferulic acid and m-coumaric acid. Life Sci. 2004 May 28;75(2):165-78. [PubMed:15120569 ]