Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-08 14:59:33 UTC |
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Update Date | 2020-11-09 23:19:44 UTC |
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HMDB ID | HMDB0029200 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ferulic acid 4-O-sulfate |
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Description | Ferulic acid 4-O-sulfate, also known as ferulate sulfate or ferulic acid sulfuric acid, 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. Ferulic acid 4-O-sulfate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Ferulic acid 4-O-sulfate. |
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Structure | COC1=C(OS(O)(=O)=O)C=CC(\C=C\C(O)=O)=C1 InChI=1S/C10H10O7S/c1-16-9-6-7(3-5-10(11)12)2-4-8(9)17-18(13,14)15/h2-6H,1H3,(H,11,12)(H,13,14,15)/b5-3+ |
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Synonyms | Value | Source |
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Ferulic acid sulfate | ChEBI | Ferulate sulfate | Generator | Ferulate sulphate | Generator | Ferulic acid sulfuric acid | Generator | Ferulic acid sulphuric acid | Generator | Ferulate 4-O-sulfate | Generator | Ferulate 4-O-sulphate | Generator | Ferulic acid 4-O-sulfuric acid | Generator | Ferulic acid 4-O-sulphuric acid | Generator | Ferulate 4-sulfate | Generator, HMDB, HMDB | Ferulate 4-sulphate | Generator, HMDB, HMDB | Ferulic acid 4-sulfuric acid | Generator, HMDB, HMDB | Ferulic acid 4-sulphuric acid | Generator, HMDB, HMDB | (2E)-3-[3-Methoxy-4-(sulfooxy)phenyl]-2-propenoic acid | HMDB | Ferulic acid 4-O-sulfate | HMDB | Ferulic acid-4'-sulfate | HMDB | (E)-Ferulic acid 4-O-sulfate | HMDB | (E)-Ferulic acid-4'-sulfate | HMDB | trans-Ferulic acid 4-O-sulfate | HMDB | trans-Ferulic acid-4'-sulfate | HMDB | Ferulic acid 4-sulfate | HMDB | (E)-Ferulic acid 4-O-sulphate | HMDB | (E)-Ferulic acid-4'-sulphate | HMDB | (E)-Ferulic acid-4’-sulfate | HMDB | (E)-Ferulic acid-4’-sulphate | HMDB | Ferulic acid 4-O-sulphate | HMDB | Ferulic acid 4-sulphate | HMDB | Ferulic acid-4'-sulphate | HMDB | Ferulic acid-4’-sulfate | HMDB | Ferulic acid-4’-sulphate | HMDB | trans-Ferulic acid 4-O-sulphate | HMDB | trans-Ferulic acid-4'-sulphate | HMDB | trans-Ferulic acid-4’-sulfate | HMDB | trans-Ferulic acid-4’-sulphate | HMDB |
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Chemical Formula | C10H10O7S |
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Average Molecular Weight | 274.247 |
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Monoisotopic Molecular Weight | 274.014723364 |
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IUPAC Name | (2E)-3-[3-methoxy-4-(sulfooxy)phenyl]prop-2-enoic acid |
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Traditional Name | (2E)-3-[3-methoxy-4-(sulfooxy)phenyl]prop-2-enoic acid |
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CAS Registry Number | 151481-53-7 |
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SMILES | COC1=C(OS(O)(=O)=O)C=CC(\C=C\C(O)=O)=C1 |
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InChI Identifier | InChI=1S/C10H10O7S/c1-16-9-6-7(3-5-10(11)12)2-4-8(9)17-18(13,14)15/h2-6H,1H3,(H,11,12)(H,13,14,15)/b5-3+ |
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InChI Key | PZPATWACAAOHTJ-HWKANZROSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Coumaric acids and derivatives |
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Alternative Parents | |
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Substituents | - Cinnamic acid
- Coumaric acid or derivatives
- Phenylsulfate
- Arylsulfate
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Styrene
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Sulfuric acid ester
- Sulfate-ester
- Sulfuric acid monoester
- Organic sulfuric acid or derivatives
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Ferulic acid 4-O-sulfate,1TMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC=C1OS(=O)(=O)O | 2483.9 | Semi standard non polar | 33892256 | Ferulic acid 4-O-sulfate,1TMS,isomer #2 | COC1=CC(/C=C/C(=O)O)=CC=C1OS(=O)(=O)O[Si](C)(C)C | 2506.1 | Semi standard non polar | 33892256 | Ferulic acid 4-O-sulfate,2TMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC=C1OS(=O)(=O)O[Si](C)(C)C | 2468.4 | Semi standard non polar | 33892256 | Ferulic acid 4-O-sulfate,2TMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC=C1OS(=O)(=O)O[Si](C)(C)C | 2482.3 | Standard non polar | 33892256 | Ferulic acid 4-O-sulfate,1TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1OS(=O)(=O)O | 2762.0 | Semi standard non polar | 33892256 | Ferulic acid 4-O-sulfate,1TBDMS,isomer #2 | COC1=CC(/C=C/C(=O)O)=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C | 2760.1 | Semi standard non polar | 33892256 | Ferulic acid 4-O-sulfate,2TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C | 3001.5 | Semi standard non polar | 33892256 | Ferulic acid 4-O-sulfate,2TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C | 3022.2 | Standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Ferulic acid 4-O-sulfate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4m-1980000000-0a04a82fe28e63433e61 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ferulic acid 4-O-sulfate GC-MS (1 TMS) - 70eV, Positive | splash10-00gi-6194000000-af9906ac00d0c397e1c1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ferulic acid 4-O-sulfate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 10V, Positive-QTOF | splash10-0a4i-0090000000-cbbeeecc312476cf7b4c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 20V, Positive-QTOF | splash10-056s-1790000000-c30f07543dbbb35fc47e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 40V, Positive-QTOF | splash10-003r-8920000000-1c33c8ea0fa1f33c6ead | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 10V, Negative-QTOF | splash10-00di-0090000000-5f31290999c27432202e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 20V, Negative-QTOF | splash10-00bc-0950000000-498bb5d6540050ba1f92 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 40V, Negative-QTOF | splash10-0059-4900000000-3eb0d6bf9f242cb7be06 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 10V, Negative-QTOF | splash10-00di-0090000000-31ce769cc85e2eadefca | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 20V, Negative-QTOF | splash10-004j-6190000000-6e72be15cb6746c0823e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 40V, Negative-QTOF | splash10-0002-9400000000-adf92ccf0dc6414f1c26 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 10V, Positive-QTOF | splash10-0a4i-0290000000-1af5b5745da90ec7f9fd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 20V, Positive-QTOF | splash10-004i-0920000000-f89ce8310fc96f9e6937 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ferulic acid 4-O-sulfate 40V, Positive-QTOF | splash10-01q9-2900000000-277ba2ff8bec524d449e | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB029900 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4878542 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 6305574 |
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PDB ID | Not Available |
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ChEBI ID | 133508 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Menozzi-Smarrito C, Wong CC, Meinl W, Glatt H, Fumeaux R, Munari C, Robert F, Williamson G, Barron D: First chemical synthesis and in vitro characterization of the potential human metabolites 5-o-feruloylquinic acid 4'-sulfate and 4'-O-glucuronide. J Agric Food Chem. 2011 May 25;59(10):5671-6. doi: 10.1021/jf200272m. Epub 2011 Apr 21. [PubMed:21417257 ]
- Amin HP, Czank C, Raheem S, Zhang Q, Botting NP, Cassidy A, Kay CD: Anthocyanins and their physiologically relevant metabolites alter the expression of IL-6 and VCAM-1 in CD40L and oxidized LDL challenged vascular endothelial cells. Mol Nutr Food Res. 2015 Jun;59(6):1095-106. doi: 10.1002/mnfr.201400803. Epub 2015 Apr 30. [PubMed:25787755 ]
- Ounnas F, Prive F, Salen P, Gaci N, Tottey W, Calani L, Bresciani L, Lopez-Gutierrez N, Hazane-Puch F, Laporte F, Brugere JF, Del Rio D, Demeilliers C, de Lorgeril M: Whole Rye Consumption Improves Blood and Liver n-3 Fatty Acid Profile and Gut Microbiota Composition in Rats. PLoS One. 2016 Feb 10;11(2):e0148118. doi: 10.1371/journal.pone.0148118. eCollection 2016. [PubMed:26862900 ]
- Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]
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