Record Information |
---|
Version | 1.0 |
---|
Created at | 2020-11-23 19:46:27 UTC |
---|
Updated at | 2021-08-19 23:59:33 UTC |
---|
NP-MRD ID | NP0003000 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | p-Coumaric acid |
---|
Provided By | BMRB |
---|
Description | 4-Hydroxycinnamic acid, also known as trans-p-hydroxycinnamate or p-coumaric acid, 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. 4-Hydroxycinnamic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxycinnamic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. p-Coumaric acid is found in Amphibolis antarctica, Amphibolis griffithii, Bergera koenegii, Carica papaya , Cymodocea rotundata, Cymodocea serrulata, Gentiana lutea L. var. aurantiaca , Halodule uninervis, Halodule wrightii, Halophila engelmannii, Halophila hawaiiana, Halophila minor, Murraya paniculata , Phyllospadix scouleri, Phyllospadix serrulatus, Phyllospadix torreyi, Posidonia australis, Posidonia oceanica , Scutellaria baicalensis , Solanum acaule, Solanum bulbocastanum, Solanum canasense, Solanum cardiophyllum, Solanum chacoense, Solanum commersonii , Solanum fendleri , Solanum hougasii, Solanum multidissectum, Solanum phureja, Solanum pinnacritisectum, Solanum stoloniferum, Solanum tarijense, Syringodium filiforme, Syringodium isoetifolium, Terminalia catappa , Terminalia chebula , Terminalia nigrovenulosa, Thalassia hemprichii, Thalassodendron ciliatum, Zostera capricorni, Zostera marina, Zostera muelleri and Zostera noltii. It was first documented in 2000 (PMID: 10706426). Based on a literature review a significant number of articles have been published on 4-Hydroxycinnamic acid (PMID: 12813346) (PMID: 15941352) (PMID: 12649063) (PMID: 17984079). |
---|
Structure | OC(=O)\C=C\C1=CC=C(O)C=C1 InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ |
---|
Synonyms | Value | Source |
---|
(2E)-3-(4-Hydroxyphenyl)acrylic acid | ChEBI | (e)-3-(4-Hydroxyphenyl)-2-propenoic acid | ChEBI | (e)-p-Coumaric acid | ChEBI | (e)-p-Hydroxycinnamic acid | ChEBI | 4'-HYDROXYCINNAMIC ACID | ChEBI | Naringeninic acid | ChEBI | p-Coumaric acid | ChEBI | trans-4-Hydroxycinnamic acid | ChEBI | trans-p-Coumaric acid | ChEBI | trans-p-Coumarinic acid | ChEBI | trans-p-Hydroxycinnamate | ChEBI | trans-p-Hydroxycinnamic acid | ChEBI | trans-4-Hydroxycinnamate | Kegg | 4-Hydroxycinnamate | Kegg | (2E)-3-(4-Hydroxyphenyl)acrylate | Generator | (e)-3-(4-Hydroxyphenyl)-2-propenoate | Generator | (e)-p-Coumarate | Generator | (e)-p-Hydroxycinnamate | Generator | 4'-HYDROXYCINNAMate | Generator | Naringeninate | Generator | p-Coumarate | Generator | trans-p-Coumarate | Generator | trans-p-Coumarinate | Generator | trans-4-Coumarate | HMDB | 3-(4-Hydroxyphenyl)-2-propenoate | HMDB | 3-(4-Hydroxyphenyl)-2-propenoic acid | HMDB | 3-(4-Hydroxyphenyl)acrylate | HMDB | 3-(4-Hydroxyphenyl)acrylic acid | HMDB | 4-Coumarate | HMDB | 4-Hydroxy cinnamate | HMDB | 4-Hydroxy cinnamic acid | HMDB | 4-Hydroxyphenylpropenoate | HMDB | 4-Hydroxyphenylpropenoic acid | HMDB | b-[4-Hydroxyphenyl]acrylate | HMDB | b-[4-Hydroxyphenyl]acrylic acid | HMDB | beta-[4-Hydroxyphenyl]acrylate | HMDB | beta-[4-Hydroxyphenyl]acrylic acid | HMDB | cis-p-Coumarate | HMDB | Hydroxycinnamate | HMDB | Hydroxycinnamic acid | HMDB | p-Cumarate | HMDB | p-Cumaric acid | HMDB | p-Hydroxycinnamate | HMDB | p-Hydroxycinnamic acid | HMDB | p-Hydroxyphenylacrylate | HMDB | p-Hydroxyphenylacrylic acid | HMDB | Para coumarate | HMDB | Para coumaric acid | HMDB | Para-coumarate | HMDB | Para-coumaric acid | HMDB | 4-Coumaric acid, (Z)-isomer | HMDB | 4-Coumaric acid, disodium salt | HMDB | 4-Coumaric acid, (e)-isomer | HMDB | p-Coumaryl alcohol | HMDB | trans-3-(4'-Hydroxyphenyl)-2-propenoic acid | HMDB | trans-HPPA | HMDB | (2E)-3-(4-Hydroxyphenyl)-2-propenoic acid | HMDB | (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid | HMDB | (e)-3-(4-Hydroxyphenyl)acrylic acid | HMDB | (e)-4-Hydroxycinnamic acid | HMDB | 4’-hydroxycinnamic acid | HMDB | p-Hydroxy-trans-cinnamic acid | HMDB | p-trans-Coumaric acid | HMDB | trans-3-(4-Hydroxyphenyl)-2-propenoic acid | HMDB | trans-4-Coumaric acid | HMDB | Β-[4-hydroxyphenyl]acrylic acid | HMDB | 4-Coumaric acid | HMDB, MeSH | 4-Hydroxycinnamic acid | ChEBI | (4-Hydroxyphenyl)acrylic acid | | Coumaric acid | |
|
---|
Chemical Formula | C9H8O3 |
---|
Average Mass | 164.1580 Da |
---|
Monoisotopic Mass | 164.04734 Da |
---|
IUPAC Name | (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid |
---|
Traditional Name | coumaric acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | OC(=O)\C=C\C1=CC=C(O)C=C1 |
---|
InChI Identifier | InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ |
---|
InChI Key | NGSWKAQJJWESNS-ZZXKWVIFSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
| Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
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-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 | Not Available |
---|
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 ]
- Phan TT, Sun L, Bay BH, Chan SY, Lee ST: Dietary compounds inhibit proliferation and contraction of keloid and hypertrophic scar-derived fibroblasts in vitro: therapeutic implication for excessive scarring. J Trauma. 2003 Jun;54(6):1212-24. [PubMed:12813346 ]
- Zhao Z, Egashira Y, Sanada H: Phenolic antioxidants richly contained in corn bran are slightly bioavailable in rats. J Agric Food Chem. 2005 Jun 15;53(12):5030-5. [PubMed:15941352 ]
- Brivet M, Garcia-Cazorla A, Lyonnet S, Dumez Y, Nassogne MC, Slama A, Boutron A, Touati G, Legrand A, Saudubray JM: Impaired mitochondrial pyruvate importation in a patient and a fetus at risk. Mol Genet Metab. 2003 Mar;78(3):186-92. [PubMed:12649063 ]
- Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
|
---|