| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2010-04-08 22:05:22 UTC |
|---|
| Update date | 2019-11-26 02:57:26 UTC |
|---|
| Primary ID | FDB002427 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | Rosmarinic acid |
|---|
| Description | Isolated 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 Number | 537-15-5 |
|---|
| Structure | |
|---|
| Synonyms | | Synonym | Source |
|---|
| Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C18H16O8 |
|---|
| IUPAC name | 3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid |
|---|
| 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+ |
|---|
| InChI Key | DOUMFZQKYFQNTF-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 Weight | 360.3148 |
|---|
| Monoisotopic Molecular Weight | 360.084517488 |
|---|
| Classification |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Phenylpropanoids and polyketides |
|---|
| Class | Cinnamic acids and derivatives |
|---|
| Sub Class | Hydroxycinnamic acids and derivatives |
|---|
| Direct Parent | Coumaric 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 Framework | Aromatic homomonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
|
| Disposition | Source: |
|---|
| Physico-Chemical Properties |
|---|
| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
|---|
| Physical state | Solid | |
|---|
| Physical Description | Not Available | |
|---|
| Mass Composition | C 60.00%; H 4.48%; O 35.52% | DFC |
|---|
| Melting Point | Mp 204° dec. | DFC |
|---|
| Boiling Point | Not Available | |
|---|
| Experimental Water Solubility | Not Available | |
|---|
| Experimental logP | Not Available | |
|---|
| Experimental pKa | Not Available | |
|---|
| Isoelectric point | Not Available | |
|---|
| Charge | Not Available | |
|---|
| Optical Rotation | [a]20D +145 | DFC |
|---|
| Spectroscopic UV Data | 329 () (MeOH) (Berdy) | DFC |
|---|
| Density | Not Available | |
|---|
| Refractive Index | Not Available | |
|---|
|
|---|
| Spectra |
|---|
| Spectra | |
|---|
| EI-MS/GC-MS | | Type | Description | Splash Key | View |
|---|
| Predicted GC-MS | Rosmarinic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a59-6429037000-febdf15ccc07a12300c9 | Spectrum | | Predicted GC-MS | Rosmarinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03ec-2901000000-a7651199b7749acc2b9f | Spectrum |
|
|---|
| MS/MS | Not Available |
|---|
| NMR | Not Available |
|---|
| External Links |
|---|
| ChemSpider ID | 4445104 |
|---|
| ChEMBL ID | CHEMBL324842 |
|---|
| KEGG Compound ID | C01850 |
|---|
| Pubchem Compound ID | 5281792 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | 17226 |
|---|
| Phenol-Explorer ID | 461 |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB03572 |
|---|
| CRC / DFC (Dictionary of Food Compounds) ID | BKF39-R:CLS91-G |
|---|
| EAFUS ID | Not Available |
|---|
| Dr. Duke ID | ROSMARINIC-ACID |
|---|
| BIGG ID | Not Available |
|---|
| KNApSAcK ID | C00002770 |
|---|
| HET ID | ROA |
|---|
| Food Biomarker Ontology | Not Available |
|---|
| VMH ID | Not Available |
|---|
| Flavornet ID | Not Available |
|---|
| GoodScent ID | Not Available |
|---|
| SuperScent ID | Not Available |
|---|
| Wikipedia ID | Rosmarinic acid |
|---|
| Phenol-Explorer Metabolite ID | 461 |
|---|
| Duplicate IDS | Not Available |
|---|
| Old DFC IDS | Not Available |
|---|
| Associated Foods |
|---|
| Food | Content Range | Average | Reference |
|---|
| Food | | | Reference |
|---|
|
| Biological Effects and Interactions |
|---|
| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
|---|
| beta inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | adenylate-cyclase inhibitor | 23924 | 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 inhibitor | 48550 | 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 aggregant | | | DUKE | | anti allergic | 50857 | A drug used to treat allergic reactions. | DUKE | | anti Alzheimeran | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti anaphylactic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti atherosclerotic | 38070 | 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 bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti coagulant | 50249 | An agent that prevents blood clotting. | DUKE | | anti complementary | | | DUKE | | anti depressant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti edemic | | | DUKE | | anti gonadotropic | | | DUKE | | anti hemolytic | 50248 | Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. | DUKE | | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti HIV | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti hyperthyroid | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti integrase | 23924 | 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 leukotriene | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | anti lipoperoxidant | | | DUKE | | anti mutagenic | | | DUKE | | anti nephritic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | antioxidant | 22586 | 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 plaque | | | DUKE | | anti proliferant | | | DUKE | | anti prostaglandin | 49020 | 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 proteolytic | | | DUKE | | anti pulmonotic | | | DUKE | | anti radicular | | | DUKE | | anti shock | | | DUKE | | anti thyreotropic | | | DUKE | | anti thyroid | | | DUKE | | anti uremic | | | DUKE | | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anxiolytic | 35474 | 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 | | apoptotic | | | DUKE | | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | cyclooxygenase-1 inhibitor | 50630 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1. | DUKE | | cyclooxygenase-2 inhibitor | 50629 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. | DUKE | | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | | deiodinase inhibitor | 23924 | 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 | | immunomodulator | 50846 | Biologically active substance whose activity affects or plays a role in the functioning of the immune system. | DUKE | | immunostimulant | 50847 | 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 inhibitor | 35856 | 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 | | neuroprotective | 63726 | Any compound that can be used for the treatment of neurodegenerative disorders. | DUKE | | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | | radioprotective | 35232 | Any pharmaceutical compound containing a radioisotope. | DUKE |
|
|---|
| Enzymes | Not Available |
|---|
| Pathways | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Biosynthesis | Not Available |
|---|
| Organoleptic Properties |
|---|
| Flavours | Not Available |
|---|
| Files |
|---|
| MSDS | Not Available |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| General Reference | Not 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.
|
|---|
