Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 22:33:27 UTC |
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Update Date | 2022-03-07 02:55:16 UTC |
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HMDB ID | HMDB0037319 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2'-O-Methylisoliquiritigenin |
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Description | 2'-O-Methylisoliquiritigenin (CAS: 51828-10-5), also known as 4,4'-dihydroxy-2'-methoxychalcone or 3-deoxysappanchalcone, belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. Thus, 2'-O-methylisoliquiritigenin is considered to be a flavonoid lipid molecule. 2'-O-Methylisoliquiritigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2'-O-Methylisoliquiritigenin is a stress metabolite of Pisum sativum (pea). |
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Structure | COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1 InChI=1S/C16H14O4/c1-20-16-10-13(18)7-8-14(16)15(19)9-4-11-2-5-12(17)6-3-11/h2-10,17-18H,1H3/b9-4+ |
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Synonyms | Value | Source |
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4,4'-Dihydroxy-2'-methoxychalcone | ChEBI | Isoliquiritigenin 2'-methy ether | HMDB | 3-Deoxysappanchalcone | MeSH, HMDB | (2E)-1-(4-Hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one | HMDB | 1-(4-Hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one | HMDB | 2'-Methoxyisoliquiritigenin | HMDB | 2'-Methylisoliquiritigenin | HMDB | 2'-O-Methylisoliquiritigenin | HMDB | 2’-Methoxyisoliquiritigenin | HMDB | 2’-Methylisoliquiritigenin | HMDB | 2’-O-Methylisoliquiritigenin | HMDB | 3-(4-Hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one | HMDB | 4,4’-Dihydroxy-2’-methoxychalcone | HMDB | Isoliquiritigenin 2'-methyl ether | HMDB | Isoliquiritigenin 2’-methyl ether | HMDB |
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Chemical Formula | C16H14O4 |
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Average Molecular Weight | 270.28 |
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Monoisotopic Molecular Weight | 270.089208936 |
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IUPAC Name | (2E)-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one |
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Traditional Name | 3-deoxysappanchalcone |
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CAS Registry Number | 112408-67-0 |
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SMILES | COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C16H14O4/c1-20-16-10-13(18)7-8-14(16)15(19)9-4-11-2-5-12(17)6-3-11/h2-10,17-18H,1H3/b9-4+ |
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InChI Key | PACBGANPVNHGNP-RUDMXATFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Linear 1,3-diarylpropanoids |
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Sub Class | Cinnamylphenols |
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Direct Parent | Cinnamylphenols |
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Alternative Parents | |
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Substituents | - Cinnamylphenol
- Hydroxycinnamic acid or derivatives
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Benzoyl
- Aryl ketone
- Styrene
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Acryloyl-group
- Alpha,beta-unsaturated ketone
- Enone
- Ketone
- Ether
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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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 | 210 - 212 °C | 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 | | Show more...
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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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2'-O-Methylisoliquiritigenin,1TMS,isomer #1 | COC1=CC(O[Si](C)(C)C)=CC=C1C(=O)/C=C/C1=CC=C(O)C=C1 | 2799.6 | Semi standard non polar | 33892256 | 2'-O-Methylisoliquiritigenin,1TMS,isomer #2 | COC1=CC(O)=CC=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1 | 2813.5 | Semi standard non polar | 33892256 | 2'-O-Methylisoliquiritigenin,2TMS,isomer #1 | COC1=CC(O[Si](C)(C)C)=CC=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1 | 2824.1 | Semi standard non polar | 33892256 | 2'-O-Methylisoliquiritigenin,1TBDMS,isomer #1 | COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C(=O)/C=C/C1=CC=C(O)C=C1 | 3063.3 | Semi standard non polar | 33892256 | 2'-O-Methylisoliquiritigenin,1TBDMS,isomer #2 | COC1=CC(O)=CC=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 3098.4 | Semi standard non polar | 33892256 | 2'-O-Methylisoliquiritigenin,2TBDMS,isomer #1 | COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 3375.3 | 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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Predicted GC-MS | Predicted GC-MS Spectrum - 2'-O-Methylisoliquiritigenin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0zfr-0970000000-da53691eb80b42283f35 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2'-O-Methylisoliquiritigenin GC-MS (2 TMS) - 70eV, Positive | splash10-006y-1249200000-6f33947cad76377fa989 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2'-O-Methylisoliquiritigenin 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin , positive-QTOF | splash10-00di-0920000000-08ee4123d744fbaeb767 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 10V, Positive-QTOF | splash10-00di-0290000000-d7f4f496b64c815f02c8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 20V, Positive-QTOF | splash10-0uka-0960000000-a4e95566966f0337e292 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 40V, Positive-QTOF | splash10-01ba-4910000000-eeafd6d970e54ae279b4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 10V, Negative-QTOF | splash10-014i-0290000000-c4e9856285707151c722 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 20V, Negative-QTOF | splash10-014i-0590000000-2242dd1e9b5a297c52a9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 40V, Negative-QTOF | splash10-06dr-5920000000-82cb523aefcbbfa3c088 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 10V, Positive-QTOF | splash10-00di-0090000000-3a2225995fb790b444d8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 20V, Positive-QTOF | splash10-0f6t-0910000000-cc4740823efa036a9fa5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 40V, Positive-QTOF | splash10-0ldi-2910000000-2eeebb03ff944c10ad39 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 10V, Negative-QTOF | splash10-014i-0290000000-aa85c230448d752d6795 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 20V, Negative-QTOF | splash10-014s-0920000000-3a2b8141d088f42fa276 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 40V, Negative-QTOF | splash10-014i-2960000000-a78eb0f3f2dfc5c55be9 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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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 | FDB016339 |
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KNApSAcK ID | C00006927 |
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Chemspider ID | 4477932 |
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KEGG Compound ID | C15531 |
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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 | 5319688 |
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PDB ID | Not Available |
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ChEBI ID | 519567 |
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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 | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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