Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:39 UTC |
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Update date | 2019-11-26 02:55:09 UTC |
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Primary ID | FDB000655 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Liquiritigenin |
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Description | Liquiritigenin belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, liquiritigenin is considered to be a flavonoid. Liquiritigenin is a bitter tasting compound. Liquiritigenin has been detected, but not quantified in, several different foods, such as nuts, winged beans (Psophocarpus tetragonolobus), brussel sprouts (Brassica oleracea var. gemmifera), green vegetables, and prairie turnips (Pediomelum esculentum). This could make liquiritigenin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Liquiritigenin. |
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CAS Number | 578-86-9 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-Liquiritigenin | ChEBI | (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | ChEBI | (2S)-Liquiritigenin | ChEBI | 4',7-Dihydroxyflavanone | ChEBI | 7,4'-Dihydroxyflavanone | ChEBI | (-)-(2S)-7,4'-Dihydroxyflavanone | HMDB | (-)-(2S)-7,4’-Dihydroxyflavanone | HMDB | (-)-(S)-4',7-Dihydroxyflavanone | HMDB | (-)-(S)-4’,7-Dihydroxyflavanone | HMDB | (2S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | HMDB | (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one | HMDB | 4’,7-Dihydroxyflavanone | HMDB | 7,4’-Dihydroxyflavanone | HMDB | Liquiritigenin | HMDB | 5-Deoxyflavanone | HMDB | DFV | HMDB | (S)-4',7-Dihydroxyflavanone | manual | 2S,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | manual | 5-DEOXYFLAVANONE | HMDB |
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Predicted Properties | |
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Chemical Formula | C15H12O4 |
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IUPAC name | (2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one |
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InChI Identifier | InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2 |
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InChI Key | FURUXTVZLHCCNA-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2 |
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Average Molecular Weight | 256.257 |
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Monoisotopic Molecular Weight | 256.073558866 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavans |
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Direct Parent | Flavanones |
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Alternative Parents | |
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Substituents | - 4'-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Flavanone
- Chromone
- Chromane
- 1-benzopyran
- Benzopyran
- Aryl alkyl ketone
- Aryl ketone
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 70.31%; H 4.72%; O 24.97% | DFC |
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Melting Point | Mp 203-205° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]25D -36.2 (c, 0.09 in MeOH) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-06vr-1290000000-473372a9cbd8aa299c8c | Spectrum | Predicted GC-MS | , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-014r-0900000000-8829ca13726fa5ef2894 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0090010000-4f0e0e7c69cd0563f154 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014r-0900000000-8829ca13726fa5ef2894 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QIT 4V, positive | splash10-0a4i-0090000000-e0ef2b922828538142d6 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QIT 15V, positive | splash10-01pa-0990000000-b55ccc74a2ff9f8ee58a | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0a4r-0690000000-e4eb8456793483d7e47b | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive | splash10-000i-0910000000-1b26412c239d13150a16 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQQ , positive | splash10-0a4i-0090000000-5a6df4ef73b17801c15b | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT 17V, positive | splash10-0a4r-0390000000-030c074282d57f882ea6 | 2020-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT 17V, positive | splash10-000j-0970000000-cc482ab502fe16da0b2c | 2020-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-014r-0900000000-8829ca13726fa5ef2894 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-7e114a20c600b4c23218 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-014i-2900000000-00ac566b03c0d20a16bc | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-014r-0900000000-37f3374e06351b592624 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-000i-0910000000-afbe3e4c5fceeb057aac | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-014i-1900000000-541af142929c530ffba1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0ap0-0970000000-5d4e47f2631f47124cc4 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0290000000-93474b44c5d1cb8cb155 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-0790000000-572e47bb5dd6e39a5083 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00rj-5910000000-47c758a4f16f999867aa | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-b48d7117a74eb8dea54d | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0290000000-24d9ef16fb94c78f6cd9 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014u-6930000000-82d8508c6ca9b5e8be2a | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-74e7833e04a924835b1e | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-0790000000-f21efeafedd047dfaebd | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 1818 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09762 |
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Pubchem Compound ID | 1889 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB03601 |
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HMDB ID | HMDB29519 |
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CRC / DFC (Dictionary of Food Compounds) ID | BFK34-C:BFK72-M |
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EAFUS ID | Not Available |
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Dr. Duke ID | LIQUIRITIGENIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000977 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Liquiritigenin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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