Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:04:39 UTC |
---|
Update date | 2019-11-26 02:55:09 UTC |
---|
Primary ID | FDB000655 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Liquiritigenin |
---|
Description | Liquiritigenin, also known as 5-deoxyflavanone or DFV, 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 lipid molecule. Liquiritigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Liquiritigenin is a bitter tasting compound. Liquiritigenin has been detected, but not quantified in, several different foods, such as peach (var.), rowanberries, common cabbages, common hazelnuts, and oyster mushrooms. This could make liquiritigenin a potential biomarker for the consumption of these foods. |
---|
CAS Number | 578-86-9 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
(-)-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 | 5-Deoxyflavanone | HMDB | DFV | HMDB | Liquiritigenin | HMDB | (S)-4',7-Dihydroxyflavanone | manual | 2S,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | manual | 5-DEOXYFLAVANONE | HMDB |
|
---|
Predicted Properties | |
---|
Chemical Formula | C15H12O4 |
---|
IUPAC name | (2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one |
---|
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 |
---|
InChI Key | FURUXTVZLHCCNA-UHFFFAOYSA-N |
---|
Isomeric SMILES | OC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2 |
---|
Average Molecular Weight | 256.257 |
---|
Monoisotopic Molecular Weight | 256.073558866 |
---|
Classification |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Flavonoids |
---|
Sub Class | Flavans |
---|
Direct Parent | Flavanones |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Ontology | No ontology term |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Not Available | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 70.31%; H 4.72%; O 24.97% | DFC |
---|
Melting Point | Mp 203-205° | DFC |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | [a]25D -36.2 (c, 0.09 in MeOH) | DFC |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-06vr-1290000000-473372a9cbd8aa299c8c | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-014r-0900000000-8829ca13726fa5ef2894 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0090010000-4f0e0e7c69cd0563f154 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014r-0900000000-8829ca13726fa5ef2894 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - QIT 4V, positive | splash10-0a4i-0090000000-e0ef2b922828538142d6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - QIT 15V, positive | splash10-01pa-0990000000-b55ccc74a2ff9f8ee58a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0a4r-0690000000-e4eb8456793483d7e47b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive | splash10-000i-0910000000-1b26412c239d13150a16 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQQ , positive | splash10-0a4i-0090000000-5a6df4ef73b17801c15b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT 17V, positive | splash10-0a4r-0390000000-030c074282d57f882ea6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT 17V, positive | splash10-000j-0970000000-cc482ab502fe16da0b2c | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0290000000-93474b44c5d1cb8cb155 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-0790000000-572e47bb5dd6e39a5083 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00rj-5910000000-47c758a4f16f999867aa | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-b48d7117a74eb8dea54d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0290000000-24d9ef16fb94c78f6cd9 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014u-6930000000-82d8508c6ca9b5e8be2a | JSpectraViewer |
|
---|
External Links |
---|
ChemSpider ID | 1818 |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | C09762 |
---|
Pubchem Compound ID | 1889 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | DB03601 |
---|
HMDB ID | HMDB29519 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | BFK34-C:BFK72-M |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | LIQUIRITIGENIN |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00000977 |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Liquiritigenin |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Flavor | Citations |
---|
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
|
|
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
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.
|
---|