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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 00:44:12 UTC
Update Date2021-09-14 15:45:11 UTC
HMDB IDHMDB0003572
Secondary Accession Numbers
  • HMDB0002887
  • HMDB0124941
  • 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 ). BioTransformer predicts that rosmarinic acid is a product of methylrosmarinic acid metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in humans and human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223 ).
Structure
Data?1601239058
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))-isomerHMDB
(R)-RosmarinateHMDB
Labiatenic acidHMDB
Labiatic acidHMDB
Rosemaric acidHMDB
trans-Rosmarinic acidHMDB
(Z)-Rosmarinic acidHMDB
Rosmarinic acidChEBI
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 Number20283-92-5
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
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
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Polarizability34.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalMetCCS_train_neg170.25930932474
AllCCS[M-H]-ExperimentalNot Available171.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000437
AllCCS[M+H]+ExperimentalNot Available169.157http://allccs.zhulab.cn/database/detail?ID=AllCCS00000437

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Rosmarinic acid,1TMS,#13588.1094https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TMS,#23532.2466https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TMS,#33514.5117https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TMS,#43521.1116https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TMS,#53519.4453https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#13402.6763https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#23419.127https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#33406.4387https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#43416.31https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#53421.167https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#63427.938https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#73459.8123https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#83418.4756https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#93418.753https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TMS,#103460.0994https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#13359.5793https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#23352.6086https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#33364.6335https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#43341.8306https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#53357.1333https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#63351.5518https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#73399.47https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#83399.9521https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#93411.3225https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TMS,#103402.4517https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TMS,#13384.5596https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TMS,#23398.3293https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TMS,#33386.7332https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TMS,#43378.559https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TMS,#53442.4644https://arxiv.org/abs/1905.12712
Rosmarinic acid,5TMS,#13424.6016https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TBDMS,#13891.5928https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TBDMS,#23850.6934https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TBDMS,#33831.724https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TBDMS,#43847.7336https://arxiv.org/abs/1905.12712
Rosmarinic acid,1TBDMS,#53841.6392https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#13984.6597https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#23986.564https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#33980.6326https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#43982.3599https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#54057.868https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#64051.7236https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#73996.1812https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#84061.4443https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#94055.8066https://arxiv.org/abs/1905.12712
Rosmarinic acid,2TBDMS,#104023.3665https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#14121.063https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#24191.3696https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#34181.1304https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#44164.9385https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#54157.2227https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#64117.841https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#74249.427https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#84229.8994https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#94231.397https://arxiv.org/abs/1905.12712
Rosmarinic acid,3TBDMS,#104255.1655https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TBDMS,#14337.728https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TBDMS,#24330.7544https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TBDMS,#34350.56https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TBDMS,#44318.4766https://arxiv.org/abs/1905.12712
Rosmarinic acid,4TBDMS,#54388.8423https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00kb-1889000000-a18403fdf27acdd9420a2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kb-1889000000-a18403fdf27acdd9420a2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03k9-0900000000-0bfd48de4c7d7947465f2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a59-6429037000-febdf15ccc07a12300c92017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0901000000-f29409b402b063dcbebd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0bt9-0907000100-ececf6d2ede2e8193b9b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03e9-0900000000-14bb8ce94558a85b706c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0902000000-f3cc2fa86fc00ea8e4742017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-0dac983721970230a2102017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0439000000-38b13aa5bfab28c4d0c22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-383db44d2370c96626662017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-008i-0679000000-629ad81e5a4aa4a45cd92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-f099de2a6e6ab011d21b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-529a6653ec4eebdd8eeb2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0239-1900000000-8bed95d3ae91d9873e982021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0902000000-36563722d30feeb69ae32021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-d32896fadf8e7c5c5fa42021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0819000000-20e9707f2681dfaa1a772016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0902000000-a28b547c92e2012a4b542016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gi-2900000000-7a9099cde66c5c7e53092016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0917000000-020d7427c4eb0534eba72016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0901000000-2beb88c288aa75c183192016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-0900000000-a99d2e96b7197132aef02016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0609000000-22da9fe5c6bdbd604e372021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0911000000-8e451eebff48555bf2da2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0080-0900000000-17f1dadda7cca4cb38f32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0906000000-94e3eda19260aae880042021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-044r-0912000000-1579343afd1e0687f73a2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0900000000-3a39bccb449c58971bdc2021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot 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 QuantifiedNot QuantifiedNot 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
Phenol Explorer Compound ID461
FooDB IDFDB002427
KNApSAcK IDC00002770
Chemspider ID4445104
KEGG Compound IDC01850
BioCyc IDCPD-6981
BiGG IDNot Available
Wikipedia LinkRosmarinic_acid
METLIN ID6960
PubChem Compound5281792
PDB IDNot Available
ChEBI ID50371
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  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 ]
  6. Haapalainen AM, Merilainen G, Pirila PL, Kondo N, Fukao T, Wierenga RK: Crystallographic and kinetic studies of human mitochondrial acetoacetyl-CoA thiolase: the importance of potassium and chloride ions for its structure and function. Biochemistry. 2007 Apr 10;46(14):4305-21. Epub 2007 Mar 20. [PubMed:17371050 ]
  7. Fukao T, Zhang GX, Sakura N, Kubo T, Yamaga H, Hazama A, Kohno Y, Matsuo N, Kondo M, Yamaguchi S, Shigematsu Y, Kondo N: The mitochondrial acetoacetyl-CoA thiolase (T2) deficiency in Japanese patients: urinary organic acid and blood acylcarnitine profiles under stable conditions have subtle abnormalities in T2-deficient patients with some residual T2 activity. J Inherit Metab Dis. 2003;26(5):423-31. [PubMed:14518824 ]
  8. Fukao T, Nakamura H, Song XQ, Nakamura K, Orii KE, Kohno Y, Kano M, Yamaguchi S, Hashimoto T, Orii T, Kondo N: Characterization of N93S, I312T, and A333P missense mutations in two Japanese families with mitochondrial acetoacetyl-CoA thiolase deficiency. Hum Mutat. 1998;12(4):245-54. [PubMed:9744475 ]
  9. Fukao T, Kodama A, Aoyanagi N, Tsukino R, Uemura S, Song XQ, Watanebe H, Kuhara T, Matsumoto I, Orii T, Kondo N: Mild form of beta-ketothiolase deficiency (mitochondrial acetoacetyl-CoA thiolase deficiency) in two Japanese siblings: identification of detectable residual activity and cross-reactive material in EB-transformed lymphocytes. Clin Genet. 1996 Oct;50(4):263-6. [PubMed:9001814 ]
  10. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]