Record Information |
---|
Version | 1.0 |
---|
Created at | 2005-11-20 22:13:20 UTC |
---|
Updated at | 2024-04-19 10:06:02 UTC |
---|
NP-MRD ID | NP0000467 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | m-Coumaric acid |
---|
Description | M-Coumaric acid, also known as 3-coumarate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. M-Coumaric acid exists in all living organisms, ranging from bacteria to humans. M-Coumaric acid (CAS: 588-30-7) Is a polyphenol metabolite from caffeic acid, formed by the gut microflora. Outside of the human body, m-Coumaric acid is found, on average, in the highest concentration within a few different foods, such as olives, corns, and beers. M-Coumaric acid has also been detected, but not quantified in several different foods, such as carrots, strawberries, grape wines, garden tomato, and bilberries. MCT-mediated absorption of phenolic compounds per se and their colonic metabolites would exert a significant impact on human health (PMID: 16870009 , 15479001 , 15479001 ). M-Coumaric acid is transported by the monocarboxylic acid transporter (MCT). The amount of this compound in human biofluids is diet-dependant. M-Coumaric acid is detected after the consumption of whole grain. |
---|
Structure | OC(=O)\C=C\C1=CC(O)=CC=C1 InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ |
---|
Synonyms | Value | Source |
---|
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid | ChEBI | (2E)-3-(3-Hydroxyphenyl)acrylic acid | ChEBI | (e)-3-(3-Hydroxyphenyl)-2-propenoic acid | ChEBI | 3-Coumaric acid | ChEBI | m-Hydroxycinnamic acid | ChEBI | trans-3-Hydroxycinnamate | ChEBI | trans-3-Hydroxycinnamic acid | ChEBI | (2E)-3-(3-Hydroxyphenyl)prop-2-enoate | Kegg | (2E)-3-(3-Hydroxyphenyl)-2-propenoate | Generator | (2E)-3-(3-Hydroxyphenyl)acrylate | Generator | (e)-3-(3-Hydroxyphenyl)-2-propenoate | Generator | 3-Coumarate | Generator | m-Hydroxycinnamate | Generator | (2E)-3-(3-Hydroxyphenyl)prop-2-enoic acid | Generator | m-Coumarate | Generator | 3'-Hydroxycinnamate | HMDB | 3'-Hydroxycinnamic acid | HMDB | 3-(3-Hydroxyphenyl)-2-propenoate | HMDB | 3-(3-Hydroxyphenyl)-2-propenoic acid | HMDB | 3-(3-Hydroxyphenyl)acrylate | HMDB | 3-(3-Hydroxyphenyl)acrylsaeure | HMDB | 3-(3-Hydroxyphenyl)prop-2-enoate | HMDB | 3-(3-Hydroxyphenyl)prop-2-enoic acid | HMDB | 3-Hydroxycinnamate | HMDB | 3-Hydroxycinnamic acid | HMDB | m-Hydroxy-cinnamate | HMDB | m-Hydroxy-cinnamic acid | HMDB | 3-Coumaric acid, (e)-isomer | HMDB | Meta-coumaric acid | HMDB | (e)-3-(3-Hydroxyphenyl)acrylic acid | HMDB | (e)-3-Hydroxycinnamic acid | HMDB | trans-3-(m-Hydroxyphenyl)-2-propenoic acid | HMDB | trans-m-Coumaric acid | HMDB | trans-m-Hydroxycinnamic acid | HMDB | trans-3-Coumarate | HMDB | 3-(3-Hydroxyphenyl)acrylic acid | HMDB | trans-3-Coumaric acid | HMDB | m-Coumaric acid | HMDB |
|
---|
Chemical Formula | C9H8O3 |
---|
Average Mass | 164.1580 Da |
---|
Monoisotopic Mass | 164.04734 Da |
---|
IUPAC Name | (2E)-3-(3-hydroxyphenyl)prop-2-enoic acid |
---|
Traditional Name | m-coumaric acid |
---|
CAS Registry Number | 588-30-7 |
---|
SMILES | OC(=O)\C=C\C1=CC(O)=CC=C1 |
---|
InChI Identifier | InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ |
---|
InChI Key | KKSDGJDHHZEWEP-SNAWJCMRSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-23 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-23 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-23 | View Spectrum | 1D NMR | [13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-23 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 800 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-23 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800.148940889 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201.216488466 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Species Where Detected | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Cinnamic acids and derivatives |
---|
Sub Class | Hydroxycinnamic acids and derivatives |
---|
Direct Parent | Hydroxycinnamic acids |
---|
Alternative Parents | |
---|
Substituents | - Cinnamic acid
- Coumaric acid
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | |
---|
Predicted Properties | |
---|
General References | - Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [PubMed:10706426 ]
- Baba S, Osakabe N, Natsume M, Yasuda A, Muto Y, Hiyoshi K, Takano H, Yoshikawa T, Terao J: Absorption, metabolism, degradation and urinary excretion of rosmarinic acid after intake of Perilla frutescens extract in humans. Eur J Nutr. 2005 Feb;44(1):1-9. Epub 2004 Feb 18. [PubMed:15309457 ]
- Gonthier MP, Verny MA, Besson C, Remesy C, Scalbert A: Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J Nutr. 2003 Jun;133(6):1853-9. [PubMed:12771329 ]
- Kim MJ, Choi SJ, Kim HK, Kim CJ, Hong B, Kim YJ, Shin DH: Activation effects of Allium tuberosum Rottl. on choline acetyltransferase. Biosci Biotechnol Biochem. 2007 Jan;71(1):226-30. Epub 2007 Jan 7. [PubMed:17213651 ]
- Shahidi F, Alasalvar C, Liyana-Pathirana CM: Antioxidant phytochemicals in hazelnut kernel (Corylus avellana L.) and hazelnut byproducts. J Agric Food Chem. 2007 Feb 21;55(4):1212-20. Epub 2007 Jan 24. [PubMed:17249682 ]
- Liu HL, Wan X, Huang XF, Kong LY: Biotransformation of sinapic acid catalyzed by Momordica charantia peroxidase. J Agric Food Chem. 2007 Feb 7;55(3):1003-8. [PubMed:17263505 ]
- Colen CB, Seraji-Bozorgzad N, Marples B, Galloway MP, Sloan AE, Mathupala SP: Metabolic remodeling of malignant gliomas for enhanced sensitization during radiotherapy: an in vitro study. Neurosurgery. 2006 Dec;59(6):1313-23; discussion 1323-4. [PubMed:17277695 ]
- Luceri C, Giannini L, Lodovici M, Antonucci E, Abbate R, Masini E, Dolara P: p-Coumaric acid, a common dietary phenol, inhibits platelet activity in vitro and in vivo. Br J Nutr. 2007 Mar;97(3):458-63. [PubMed:17313706 ]
- Funk C, Braune A, Grabber JH, Steinhart H, Bunzel M: Moderate ferulate and diferulate levels do not impede maize cell wall degradation by human intestinal microbiota. J Agric Food Chem. 2007 Mar 21;55(6):2418-23. Epub 2007 Feb 24. [PubMed:17319685 ]
- Grande MJ, Lopez RL, Abriouel H, Valdivia E, Ben Omar N, Maqueda M, Martinez-Canamero M, Galvez A: Treatment of vegetable sauces with enterocin AS-48 alone or in combination with phenolic compounds to inhibit proliferation of Staphylococcus aureus. J Food Prot. 2007 Feb;70(2):405-11. [PubMed:17340876 ]
- Ibanez AJ, Muck A, Svatos A: Dissipation of charge on MALDI-TOF polymeric chips using an electron-acceptor: analysis of proteins. J Mass Spectrom. 2007 May;42(5):634-40. [PubMed:17370249 ]
- Efdi M, Itoh T, Akao Y, Nozawa Y, Koketsu M, Ishihara H: The isolation of secondary metabolites and in vitro potent anti-cancer activity of clerodermic acid from Enicosanthum membranifolium. Bioorg Med Chem. 2007 Jun 1;15(11):3667-71. Epub 2007 Mar 18. [PubMed:17400462 ]
- Azzini E, Bugianesi R, Romano F, Di Venere D, Miccadei S, Durazzo A, Foddai MS, Catasta G, Linsalata V, Maiani G: Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads of Cynara scolymus L. (cultivar Violetto di Provenza) in human subjects: a pilot study. Br J Nutr. 2007 May;97(5):963-9. [PubMed:17408528 ]
- Appiah-Opong R, Commandeur JN, van Vugt-Lussenburg B, Vermeulen NP: Inhibition of human recombinant cytochrome P450s by curcumin and curcumin decomposition products. Toxicology. 2007 Jun 3;235(1-2):83-91. Epub 2007 Mar 15. [PubMed:17433521 ]
- Wang Q, Morris ME: The role of monocarboxylate transporter 2 and 4 in the transport of gamma-hydroxybutyric acid in mammalian cells. Drug Metab Dispos. 2007 Aug;35(8):1393-9. Epub 2007 May 14. [PubMed:17502341 ]
- Keyhanian S, Stahl-Biskup E: Phenolic constituents in dried flowers of aloe vera (Aloe barbadensis) and their in vitro antioxidative capacity. Planta Med. 2007 Jun;73(6):599-602. Epub 2007 May 22. [PubMed:17520524 ]
- Kosanam H, Prakash PK, Yates CR, Miller DD, Ramagiri S: Rapid screening of doping agents in human urine by vacuum MALDI-linear ion trap mass spectrometry. Anal Chem. 2007 Aug 1;79(15):6020-6. Epub 2007 Jun 30. [PubMed:17602668 ]
- Rakotondramanana DL, Delomenede M, Baltas M, Duran H, Bedos-Belval F, Rasoanaivo P, Negre-Salvayre A, Gornitzka H: Synthesis of ferulic ester dimers, functionalisation and biological evaluation as potential antiatherogenic and antiplasmodial agents. Bioorg Med Chem. 2007 Sep 15;15(18):6018-26. Epub 2007 Jun 29. [PubMed:17624792 ]
- Gomez-Ruiz JA, Leake DS, Ames JM: In vitro antioxidant activity of coffee compounds and their metabolites. J Agric Food Chem. 2007 Aug 22;55(17):6962-9. Epub 2007 Jul 27. [PubMed:17655324 ]
- Wu CI, Tsai CC, Lu CC, Wu PC, Wu DC, Lin SY, Shiea J: Diagnosis of occult blood in human feces using matrix-assisted laser desorption ionization/time-of-flight mass spectrometry. Clin Chim Acta. 2007 Sep;384(1-2):86-92. Epub 2007 Jun 26. [PubMed:17662705 ]
- Henry BL, Monien BH, Bock PE, Desai UR: A novel allosteric pathway of thrombin inhibition: Exosite II mediated potent inhibition of thrombin by chemo-enzymatic, sulfated dehydropolymers of 4-hydroxycinnamic acids. J Biol Chem. 2007 Nov 2;282(44):31891-9. Epub 2007 Sep 5. [PubMed:17804413 ]
- Qin J, Chen D, Hu H, Qiao M, Zhao X, Chen B: Body distributioin of RGD-mediated liposome in brain-targeting drug delivery. Yakugaku Zasshi. 2007 Sep;127(9):1497-501. [PubMed:17827930 ]
- Monteiro M, Farah A, Perrone D, Trugo LC, Donangelo C: Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J Nutr. 2007 Oct;137(10):2196-201. [PubMed:17884997 ]
- Mennen LI, Sapinho D, Ito H, Bertrais S, Galan P, Hercberg S, Scalbert A: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. Br J Nutr. 2006 Jul;96(1):191-8. [PubMed:16870009 ]
- Konishi Y, Kobayashi S: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2004 Oct 20;52(21):6418-24. [PubMed:15479001 ]
|
---|