PhytoHub: Showing entry for Rosmarinic acid

Rosmarinic acid

Identification

PhytoHub ID

PHUB000634

Name

Rosmarinic acid

Systematic Name

Rosmarinic acid

Synonyms

Not Available

CAS Number

Not Available

Average Mass

360.318

Monoisotopic Mass

360.084517475

Chemical Formula

C₁₈H₁₆O₈

IUPAC Name

(2S)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid

InChI Key

DOUMFZQKYFQNTF-GIZXNFQBSA-N

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-/m0/s1

SMILES

OC(=O)[C@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 4.07e-02 g/l
LogS (ALOGPS): -3.95
LogP (ALOGPS): 2.57
Hydrogen Acceptors: 7
Hydrogen Donors: 5
Rotatable Bond Count: 7
Polar Surface Area: 144.52
Refractivity: 90.9501
Polarizability: 34.34113577057401
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -6.283762279508309
pKa (strongest acidic): 3.1312932183061957
Number of Rings: 2
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 639655
ChEBI: 50372
MetaboLights: MTBLC50372
PeakForestCompound: 000495

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Phenolic acids
Sub-class: Hydroxycinnamic acids

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Cinnamic acids and derivatives
Super-class: Phenylpropanoids and polyketides
Sub-class: Hydroxycinnamic acids and derivatives
Direct Parent Name: Coumaric acids and derivatives
Alternative Parent Names: ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Cinnamic acid esters", "Dicarboxylic acids and derivatives", "Enoate esters", "Fatty acid esters", "Hydrocarbon derivatives", "Organic oxides", "Phenylpropanoic acids", "Styrenes"]
External Descriptor Annotations: ["rosmarinic acid"]
Substituent Names: ["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3-phenylpropanoic-acid", "Alpha,beta-unsaturated carboxylic ester", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid ester", "Catechol", "Cinnamic acid ester", "Coumaric acid or derivatives", "Dicarboxylic acid or derivatives", "Enoate ester", "Fatty acid ester", "Fatty acyl", "Hydrocarbon derivative", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Styrene"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

LC-MS/MS	ESI- LC-Q-TOF/MS	Negative	low	View Spectrum	(72.9944,0.155);(123.0454,0.126);(132.0219,0.052);(133.0297,0.306);(135.0452,0.252);(161.0243,0.999);(179.0356,0.175);(197.0456,0.269);(359.0767,0.185)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(109.0289544,1.27857717);(111.0446045,0.4681919864);(123.0446045,2.769148311);(125.0602545,2.03468214);(133.0289544,0.2475823864);(135.0446045,1.496977257);(151.0395191,0.8661886489);(161.023869,2.258943229);(163.0395191,16.35340529);(165.0551691,1.942735792);(167.0708192,0.4601018683);(179.0344337,1.887767474);(181.0500838,6.699983796);(183.0657338,0.7407500558);(199.0606485,6.084395312);(221.0449984,0.4036119774);(225.039913,0.2491740959);(233.0449984,0.4778473676);(237.039913,1.590214289);(239.0555631,1.35539481);(247.0242629,0.3085702289);(249.039913,0.366575685);(251.0555631,1.210883871);(253.0712131,0.6820794143);(265.0712131,0.2659116876);(315.0868632,1.418800173);(317.1025133,0.2847979573);(325.0712131,1.826812913);(331.0817778,0.7030381464);(343.0817778,16.22754885);(361.0923425,27.03930782)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(105.0340398,0.6845864237);(109.0289544,2.596035173);(123.0446045,7.603742309);(125.0602545,1.05737948);(133.0289544,2.480011101);(135.0446045,6.736510507);(137.0602545,2.849509742);(151.0395191,3.750004731);(153.0551691,1.018815013);(155.0708192,0.9079513388);(161.023869,2.018978269);(163.0395191,19.83422031);(165.0551691,2.891037915);(169.0500838,1.534685899);(179.0344337,1.424526343);(181.0500838,6.630361935);(183.0657338,1.666888629);(199.0606485,7.65327138);(233.0449984,1.171057138);(237.039913,1.354759131);(249.039913,0.7324141838);(251.0555631,1.655878331);(253.0712131,0.7044891375);(275.0555631,0.8467343908);(277.0712131,1.00798761);(287.0555631,0.6598861485);(315.0868632,3.684501492);(325.0712131,1.359283914);(331.0817778,3.508629207);(343.0817778,5.83207715);(361.0923425,4.143785667)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(51.0234751,2.25425004);(55.01838972,1.490445675);(67.05477522,1.526858219);(71.01330434,3.749857736);(75.00821896,1.569345959);(77.03912516,1.662026127);(79.01838972,1.97949417);(89.02386902,0.8901596055);(97.0289544,1.389012534);(105.0340398,4.519141116);(107.0496898,2.036767363);(109.0289544,8.32711872);(111.0446045,0.9793105541);(123.0446045,17.520041);(125.0602545,3.775752306);(133.0289544,4.046657302);(135.0446045,7.039122103);(137.0602545,3.062235519);(151.0395191,4.027428702);(161.023869,1.556140358);(163.0395191,6.336873896);(165.0551691,0.9715048486);(177.0187836,1.042732037);(181.0500838,7.305712865);(193.0500838,1.235158684);(221.0449984,1.026863443);(287.0555631,1.303905005);(303.0868632,2.236349171);(305.1025133,1.127817785);(331.0817778,1.093417533);(343.0817778,2.918499625)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(44.99765427,0.1951231073);(71.01330434,0.2161213185);(72.99256889,1.369752774);(75.00821896,0.5681911609);(109.0289544,1.117178971);(121.0289544,0.4181399018);(123.0446045,0.5472101324);(133.0289544,0.3013491663);(135.0446045,2.252099025);(137.0602545,0.2010733986);(149.023869,0.2020636585);(151.0395191,0.6265725914);(153.0551691,1.05815047);(159.008219,0.2650305374);(161.023869,8.206098348);(175.0031336,0.5863844488);(177.0187836,1.053394019);(179.0344337,19.80209301);(181.0500838,0.3756381336);(197.0449984,12.19137198);(219.0293483,0.354170235);(235.0242629,2.434860494);(237.039913,2.432708628);(249.039913,0.4390618594);(251.0555631,1.058783867);(301.0712131,0.19790054);(313.0712131,1.323527517);(315.0868632,3.908674407);(317.0661278,0.2815944151);(341.0661278,1.232740268);(359.0766924,34.78294162)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(71.01330434,1.286905925);(72.99256889,1.358060901);(87.00821896,0.6291831727);(89.02386902,0.6181718924);(109.0289544,1.126164745);(121.0289544,5.296102442);(123.0446045,2.778289997);(133.0289544,1.062501792);(135.0446045,6.913521666);(137.023869,0.6860917393);(137.0602545,1.162360287);(149.023869,1.543386803);(151.0395191,3.673477731);(153.0551691,2.953353879);(161.023869,12.68205147);(175.0031336,0.5321197191);(177.0187836,0.8368873361);(179.0344337,29.05992305);(191.0344337,0.7159398709);(193.0500838,0.7270642286);(197.0449984,6.207909464);(205.0500838,0.4628045549);(235.0242629,1.477474579);(237.039913,2.358913815);(249.039913,0.548328617);(251.0555631,1.570509819);(313.0712131,1.612887291);(315.0868632,3.700320597);(317.0661278,0.8133709567);(341.0661278,1.192615193);(359.0766924,4.413306464)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00273965,1.205925075);(44.99765427,2.794367124);(47.01330434,0.5423440402);(68.99765427,0.9147333852);(71.01330434,0.4634757591);(72.99256889,0.9061878284);(87.00821896,1.303656449);(89.02386902,0.4658610292);(107.0133043,1.148735549);(109.0289544,2.564252899);(119.0133043,0.9689255533);(121.0289544,1.50004318);(123.0446045,1.949808752);(131.0133043,1.626954984);(133.0289544,4.296692784);(135.008219,1.215672221);(135.0446045,9.858094176);(137.023869,1.001403776);(137.0602545,0.5904608515);(143.0133043,0.5605647063);(147.008219,1.015384189);(149.023869,4.324007549);(151.0395191,6.657184861);(153.0551691,3.178170601);(161.023869,27.1091765);(163.0395191,1.022876864);(179.0344337,17.29288166);(183.0657338,0.5198102146);(191.0344337,1.899711819);(193.0500838,0.5235556028);(197.0449984,0.5790800203)

Food Sources

Name	Group
Common oregano	Herbs and Spices	Publications	Show
Common sage	Herbs and Spices	Publications	Show
Common thyme	Herbs and Spices	Publications	Show
Mint	Herbs and Spices	Publications	Show
Peppermint	Herbs and Spices	Publications	Show
Rosemary	Herbs and Spices	Publications	Show
Sweet basil	Herbs and Spices	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food Phytochemical	Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
Rosmarinic acid	Caffeic acid	rat	urine	Not Available	Not Available	Not Available	Not Available	C₉H₈O₄	180.042258738		Publications
Rosmarinic acid	Coumaric acid (m-)	rat	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₉H₈O₃	164.047344118		Publications
Rosmarinic acid	Rosmarinic acid	human	serum, urine	unchanged	1h-3h	50-200 nmol/L	<1%	C₁₈H₁₆O₈	360.084517475	Detailed Intervention Studies	Publications
Rosmarinic acid	3-(3'-Hydroxyphenyl)propionic acid	rat	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₉H₁₀O₃	166.062994182		Publications
Rosmarinic acid	Ferulic acid-4'-sulfate	rat	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₁₀H₁₀O₇S	274.014723836		Publications
Rosmarinic acid	caffeic acid-4-O-sulfate	rat	urine	Not Available	Not Available	Not Available	Not Available	C₉H₈O₇S	259.999073772		Publications
Rosmarinic acid	m-coumaric acid 3-O-sulfate	rat	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₉H₈O₆S	244.004159152		Publications
Rosmarinic acid	3,3'-Dimethoxyrosmarinic acid-4-glucuronide	human	plasma, urine	host metabolism	1h-3h	50-200 nmol/L	<1%	C₂₆H₂₈O₁₄	564.147905582		Publications
Rosmarinic acid	3'-Methoxyrosmarinic acid-4'-glucuronide	human	plasma, urine	host metabolism	1h-3h	20-50 nmol/L	<1%	C₂₅H₂₆O₁₄	550.132255517		Publications
Rosmarinic acid	Dimethoxyrosmarinic acid-sulfate	human	urine	host metabolism	Not Available	Not Available	<1%				Publications
Rosmarinic acid	3',4-Dimethoxyrosmarinic acid	human	plasma	host metabolism	<1h	50-200 nmol/L	Not Available	C₂₀H₂₀O₈	388.115817604		Publications
Rosmarinic acid	Methoxyrosmarinic acid-sulfate	human	urine	host metabolism	Not Available	Not Available	<1%				Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

Back

Showing entry for Rosmarinic acid