Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2019-11-26 02:57:26 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
R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionateGenerator
RosmarinateGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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

Source:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRosmarinic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a59-6429037000-febdf15ccc07a12300c9Spectrum
Predicted GC-MSRosmarinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ec-2901000000-a7651199b7749acc2b9fSpectrum
MS/MSNot Available
NMRNot Available
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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 An agent that blocks beta receptors, reducing heart rate and blood pressure. Therapeutically, it manages cardiovascular conditions such as hypertension, angina, and heart failure, while also treating conditions like glaucoma and migraines.DUKE
Adenylate-cyclase inhibitor23924 An agent that blocks adenylate cyclase, reducing cyclic AMP production. It regulates cellular signaling, and its therapeutic applications include treating conditions like heart failure and asthma, with key medical uses in managing cardiovascular and respiratory diseases.DUKE
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti-anaphylactic52217 An agent that prevents or treats anaphylaxis, a severe allergic reaction. It plays a biological role in stabilizing mast cells and reducing histamine release. Therapeutically, it is used to manage allergic emergencies, with key medical applications including treatment of anaphylactic shock, asthma, and allergic rhinitis.DUKE
Anti-atherosclerotic38070 An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti coagulant50249 An agent that prevents blood clot formation, playing a crucial role in maintaining blood fluidity. Therapeutically, it is used to treat and prevent thrombosis, embolism, and stroke, commonly used in managing conditions such as atrial fibrillation, deep vein thrombosis, and pulmonary embolism.DUKE
Anti complementaryA substance that diminishes or abolishes the action of a complement, playing a role in regulating the immune system. Therapeutically, it's used to prevent excessive inflammation and tissue damage. Key medical uses include treating autoimmune disorders, transplant rejection, and inflammatory diseases.DUKE
Anti depressant52217 An agent that regulates mood, reducing symptoms of depression and anxiety by altering neurotransmitter levels in the brain, commonly used in managing depression, anxiety disorders, and other mood disorders.DUKE
Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
Anti gonadotropicAn agent that suppresses gonadotropin activity, specifically follicle-stimulating hormone (FSH) and luteinizing hormone (LH). Used to treat hormonally-sensitive cancers, delay puberty, and manage conditions like endometriosis and hypersexuality.DUKE
Anti-hemolytic50248 An agent that prevents or reduces the breakdown of red blood cells, used to treat conditions such as hemolytic anemia, and other disorders where red blood cell destruction occurs, promoting healthy red blood cell count and preventing related complications.DUKE
Anti hepatotoxic62868 An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.DUKE
Anti-herpetic22587 An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti hyperthyroid52217 An agent that reduces thyroid hormone production, used to manage hyperthyroidism by decreasing thyroid-stimulating hormone (TSH) and thyroid hormone levels, commonly used to treat conditions such as Graves' disease and thyroid storm.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-integrase23924 An agent that blocks the activity of integrase, an enzyme essential for HIV replication, reducing viral integration into host DNA. Therapeutically, it's used to treat HIV infection, preventing the virus from replicating and slowing disease progression, commonly used in combination with other antiretroviral therapies.DUKE
Anti leukotriene35222 An agent that blocks the action of leukotrienes, reducing inflammation and bronchoconstriction. Therapeutically, it is used to treat asthma, allergic rhinitis, and other respiratory disorders by inhibiting the biological role of leukotrienes in mediating inflammatory responses.DUKE
Anti lipoperoxidantAn agent that prevents peroxidation of lipids, reducing oxidative stress and cell damage. Its biological role involves protecting cell membranes from degradation. Therapeutically, it has applications in managing conditions related to oxidative stress, with key medical uses including neuroprotection, anti-inflammation, and antioxidant therapy.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti nephritic52217 An agent that reduces kidney inflammation, commonly used to manage nephritis and other kidney disorders, helping to prevent kidney damage and promote renal health.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-plaqueAn agent that removes or prevents the formation of dental plaque, a biofilm of bacteria, to prevent tooth decay and gum disease, commonly used in oral care products and therapeutic applications for periodontal health.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
Anti-proteolyticAn agent that prevents digestion of proteins, playing a biological role in protecting tissues from damage. Therapeutically, it's used to manage conditions like pancreatitis and ulcers, with key medical applications in reducing inflammation and promoting wound healing.DUKE
Anti-pulmonoticAn agent that reduces inflammation and congestion in the lungs, commonly used in managing respiratory disorders such as asthma and chronic obstructive pulmonary disease (COPD), to improve breathing and overall pulmonary function.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Anti-shockAn agent that stabilizes blood pressure and circulation, reducing the effects of shock. Therapeutically, it's used to manage hypovolemic shock, anaphylactic shock, and septic shock, helping to prevent organ failure and promote recovery. Key medical uses include treatment of severe blood loss, burns, and trauma.DUKE
Anti-thyreotropicAn antibody that inhibits thyrotropin, regulating thyroid hormone production. It has therapeutic applications in managing thyroid disorders, such as hyperthyroidism, and key medical uses include treating conditions like Graves' disease.DUKE
Anti-thyroidAn agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease.DUKE
Anti uremicAn agent that reduces urea levels in the body, mitigating kidney injury or failure. It plays a biological role in regulating nitrogen waste, and has therapeutic applications in managing uremia, a condition characterized by elevated urea levels. Key medical uses include treating kidney disease, acute kidney injury, and end-stage renal disease.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Anxiolytic35474 An agent that reduces anxiety symptoms, commonly used in managing anxiety disorders, such as generalized anxiety disorder and panic disorder, by modulating neurotransmitters like GABA, promoting relaxation and calming effects.DUKE
ApoptoticAn agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Cyclooxygenase-1 inhibitor50630 An agent that blocks the activity of cyclooxygenase-1 (COX-1), reducing inflammation and pain. Therapeutically, it is used to manage conditions like arthritis, and as a nonsteroidal anti-inflammatory drug (NSAID) to relieve pain, fever, and inflammation, while minimizing gastrointestinal side effects.DUKE
Cyclooxygenase-2 inhibitor50629 An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
Deiodinase inhibitor23924 An agent that blocks the activity of deiodinases, enzymes involved in thyroid hormone regulation. It reduces thyroid hormone conversion, commonly used in managing thyroid disorders, such as hyperthyroidism, and certain types of cancer, including thyroid cancer.DUKE
Immunomodulator50846 An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.DUKE
Neuroprotective63726 An agent that protects nerve cells from damage or degeneration, reducing the risk of neurodegenerative diseases. Therapeutically, it helps manage conditions like Alzheimer's, Parkinson's, and stroke, promoting neuronal survival and function.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Radioprotective35232 An agent that shields cells from radiation damage, reducing oxidative stress and DNA harm. Its biological role is to mitigate radiation-induced injury, and it has therapeutic applications in cancer treatment, space exploration, and nuclear medicine, with key medical uses including protection of healthy tissues during radiation therapy.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.