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Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 17:50:48 UTC |
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Update Date | 2022-03-07 02:53:24 UTC |
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HMDB ID | HMDB0032616 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Sinapic acid |
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Description | Sinapic acid, also known as sinapinATE, 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. Sinapic acid is an odorless tasting compound. Sinapic acid is found, on average, in the highest concentration within a few different foods, such as sunflowers (Helianthus annuus), olives (Olea europaea), and garden onions (Allium cepa) and in a lower concentration in hard wheats (Triticum durum), rapes (Brassica napus var. napus), and garlics (Allium sativum). Sinapic acid has also been detected, but not quantified in, several different foods, such as chives (Allium schoenoprasum), teffs (Eragrostis tef), celeriacs (Apium graveolens var. rapaceum), yardlong beans (Vigna unguiculata ssp. sesquipedalis), and pepper (c. pubescens). This could make sinapic acid a potential biomarker for the consumption of these foods. Sinapic 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. Based on a literature review very few articles have been published on Sinapic acid. |
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Structure | COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+ |
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Synonyms | Value | Source |
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(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid | ChEBI | SINAPINATE | ChEBI | Sinapinic acid | ChEBI | 3,5-Dimethoxy-4-hydroxycinnamic acid | Kegg | (e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoate | Generator | 3,5-Dimethoxy-4-hydroxycinnamate | Generator | Sinapate | Generator | (2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid | HMDB | (2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid | HMDB | (2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid | HMDB | 3-(4-Hydroxy-3,5-dimethoxyphenyl)-(2E)-2-propenoic acid | HMDB | 3-(4-Hydroxy-3,5-dimethoxyphenyl)-(e)-2-propenoic acid | HMDB | 3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid | HMDB | 3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid | HMDB | 4-Hydroxy-3,5-dimethoxy-(e)-cinnamic acid | HMDB | 4-Hydroxy-3,5-dimethoxycinnamic acid | HMDB | trans-3,5-Dimethoxy-4-hydroxycinnamic acid | HMDB | Sinapic acid | ChEBI | trans-Sinapate | Generator, HMDB | (e)-Sinapic acid | MeSH, HMDB | Synapitic acid | MeSH, HMDB | trans-Sinapinic acid | MeSH, HMDB | (E)-3,5-Dimethoxy-4-hydroxycinnamic acid | HMDB | (E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid | HMDB | (E)-Sinapic acid | HMDB | 3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid | HMDB | E-Sinapinic acid | HMDB | trans-4-Hydroxy-3,5-dimethoxycinnamic acid | HMDB | trans-Sinapic acid | HMDB |
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Chemical Formula | C11H12O5 |
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Average Molecular Weight | 224.21 |
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Monoisotopic Molecular Weight | 224.068473494 |
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IUPAC Name | (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid |
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Traditional Name | sinapinic acid |
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CAS Registry Number | 7362-37-0 |
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SMILES | COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O |
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InChI Identifier | InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+ |
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InChI Key | PCMORTLOPMLEFB-ONEGZZNKSA-N |
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Chemical Taxonomy |
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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. |
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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 | Hydroxycinnamic acids |
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Alternative Parents | |
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Substituents | - Cinnamic acid
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- M-dimethoxybenzene
- Dimethoxybenzene
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Styrene
- Phenol ether
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Ether
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | - 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid (CHEBI:15714 )
- Sinapate derivatives (C00482 )
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Ontology |
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Disposition
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Biological location
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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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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Sinapic acid,1TMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1O | 2214.3 | Semi standard non polar | 33892256 | Sinapic acid,1TMS,isomer #2 | COC1=CC(/C=C/C(=O)O)=CC(OC)=C1O[Si](C)(C)C | 2169.8 | Semi standard non polar | 33892256 | Sinapic acid,2TMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C | 2201.5 | Semi standard non polar | 33892256 | Sinapic acid,1TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O | 2477.7 | Semi standard non polar | 33892256 | Sinapic acid,1TBDMS,isomer #2 | COC1=CC(/C=C/C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C | 2451.1 | Semi standard non polar | 33892256 | Sinapic acid,2TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C | 2735.3 | Semi 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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Experimental GC-MS | GC-MS Spectrum - Sinapic acid GC-MS (2 TMS) | splash10-00kr-3759000000-26099df97cd2adef2dc3 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Sinapic acid EI-B (Non-derivatized) | splash10-00di-4390000000-ce04c31c3e4023faa7ee | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized) | splash10-00kr-2759000000-404687968a18ced29cd9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized) | splash10-00kr-1869000000-618d42ab9681ecb06228 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized) | splash10-00di-9535000000-dc1aa60962d61ce2d9bb | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized) | splash10-00di-9636000000-15691f6a00fd74dadf7a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Sinapic acid GC-MS (Non-derivatized) | splash10-00kr-3759000000-26099df97cd2adef2dc3 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized) | splash10-000i-1966000000-84b6d21b3c65f74d1b2d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sinapic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-05di-1950000000-308e223e0595ec83666c | 2017-07-27 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sinapic acid GC-MS (2 TMS) - 70eV, Positive | splash10-0umi-8196000000-afceb35e7a5f28ec225c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sinapic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-00di-5590000000-92339c0e84f7bfd7f855 | 2015-03-01 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid DI-ESI-qTof , Positive-QTOF | splash10-002e-0900000000-c7f7d78d04b4c61a02e1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid DI-ESI-qTof , Negative-QTOF | splash10-0007-0900000000-76cfe991af651e6cec19 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOF | splash10-00di-0290000000-475d3684fdd4228e9c5d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOF | splash10-08fr-0940000000-780771eea370a78b609a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOF | splash10-0002-1900000000-3e127fbdcf11519a02f3 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOF | splash10-00dl-3900000000-d41ed2853570e017a98c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOF | splash10-006x-9600000000-668bfef76d2c29514216 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QTOF , negative-QTOF | splash10-00di-1950000000-845dcc12144449b6b8c5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QTOF , negative-QTOF | splash10-074m-1940000000-4eaf9a539449ae53a970 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QTOF , positive-QTOF | splash10-0a4i-1590000000-f69ac29a002b25accd73 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid LC-ESI-QTOF , positive-QTOF | splash10-0ar4-3940000000-64d09640303051f3b774 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOF | splash10-0006-9500000000-8fb01ded8d8100c7badf | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOF | splash10-0006-9100000000-6b4758d6474e1684747b | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOF | splash10-00dl-2900000000-512d339f4cd5c1a36d79 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOF | splash10-00di-2900000000-f1f1c513515bb228b410 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOF | splash10-08mm-0930000000-725b42822634411b06e1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOF | splash10-00kf-9400000000-e70224cdae252d3c8e18 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid 40V, Positive-QTOF | splash10-0006-9200000000-45fe03024d3082fc695e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sinapic acid 20V, Negative-QTOF | splash10-0btc-0940000000-61107acc0e4d467950bf | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sinapic acid 10V, Positive-QTOF | splash10-056r-0190000000-6e81a94093485194a43f | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sinapic acid 20V, Positive-QTOF | splash10-004i-1960000000-18717b9e874f0901ea68 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sinapic acid 40V, Positive-QTOF | splash10-06vj-2900000000-254ee08e710708eb6545 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sinapic acid 10V, Negative-QTOF | splash10-00di-0190000000-89ae701e731ef1f24fd7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sinapic acid 20V, Negative-QTOF | splash10-00di-0890000000-74c0bdbe7769b328017a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sinapic acid 40V, Negative-QTOF | splash10-0a4i-1910000000-69bbc48ce24397a342a2 | 2016-08-03 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Biological Properties |
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Cellular Locations | |
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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 | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 464 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 464 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 464 | | 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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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB08587 |
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Phenol Explorer Compound ID | 464 |
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FooDB ID | FDB010557 |
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KNApSAcK ID | C00002776 |
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Chemspider ID | 553361 |
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KEGG Compound ID | C00482 |
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BioCyc ID | SINAPATE |
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BiGG ID | Not Available |
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Wikipedia Link | Sinapinic_acid |
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METLIN ID | Not Available |
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PubChem Compound | 637775 |
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PDB ID | Not Available |
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ChEBI ID | 15714 |
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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 | rw1548161 |
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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 | - Yun KJ, Koh DJ, Kim SH, Park SJ, Ryu JH, Kim DG, Lee JY, Lee KT: Anti-inflammatory effects of sinapic acid through the suppression of inducible nitric oxide synthase, cyclooxygase-2, and proinflammatory cytokines expressions via nuclear factor-kappaB inactivation. J Agric Food Chem. 2008 Nov 12;56(21):10265-72. doi: 10.1021/jf802095g. Epub 2008 Oct 9. [PubMed:18841975 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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