Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:40 UTC |
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Update date | 2020-09-17 15:39:05 UTC |
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Primary ID | FDB000678 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (S)-Naringenin |
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Description | Naringenin, also known as (2S)-naringenin or naringetol, 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, naringenin is considered to be a flavonoid lipid molecule. The (S)-enantiomer of naringenin. Naringenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Naringenin exists in all living organisms, ranging from bacteria to humans. Naringenin is a bitter tasting compound. Outside of the human body, Naringenin is found, on average, in the highest concentration within a few different foods, such as sweet oranges, common oregano, and mexican oregano and in a lower concentration in sorghums, grape wines, and mandarin orange (clementine, tangerine). Naringenin has also been detected, but not quantified in, several different foods, such as saffrons, white lupines, alpine sweetvetchs, dates, and elderberries. This could make naringenin a potential biomarker for the consumption of these foods. |
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CAS Number | 480-41-1 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-(2S)-Naringenin | ChEBI | (2S)-Naringenin | ChEBI | (S)-2,3-Dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | ChEBI | 4',5,7-Trihydroxyflavanone | ChEBI | Naringetol | ChEBI | Pelargidanon | ChEBI | Salipurpol | ChEBI | (-)-Naringenin | HMDB | Asahina | HMDB | Naringenine | HMDB | Salipurol | HMDB | (2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | PhytoBank | (2S)-4',5,7-Trihydroxyflavanone | PhytoBank | (2S)-4’,5,7-Trihydroxyflavanone | PhytoBank | (S)-Naringenin | PhytoBank | S-Dihydrogenistein | PhytoBank | 5,7,4'-Trihydroxyflavanone | PhytoBank | 5,7,4’-Trihydroxyflavanone | PhytoBank | (-)-(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one | biospider | (2S)-4',5,7-Trihydroxy-flavanone | manual | 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- | manual | Naringenin | biospider |
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Predicted Properties | |
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Chemical Formula | C15H12O5 |
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IUPAC name | (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one |
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InChI Identifier | InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1 |
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InChI Key | FTVWIRXFELQLPI-ZDUSSCGKSA-N |
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Isomeric SMILES | [H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1 |
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Average Molecular Weight | 272.2528 |
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Monoisotopic Molecular Weight | 272.068473494 |
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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 | - Flavanone
- Hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Chromone
- Benzopyran
- Chromane
- 1-benzopyran
- Aryl alkyl ketone
- Aryl ketone
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Benzenoid
- Vinylogous acid
- Ketone
- Organoheterocyclic compound
- Oxacycle
- Ether
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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Foods | Fruits and vegetables: |
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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 | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 66.17%; H 4.44%; O 29.38% | DFC |
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Melting Point | Mp 250-251° (227-228°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 2.52 | PERRISSOUD,D & TESTA,B (1986) |
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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]27D -22.5 (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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GC-MS | (S)-Naringenin, non-derivatized, GC-MS Spectrum | splash10-00fs-1951400000-0e93ea96a72cb2a5a868 | Spectrum | GC-MS | (S)-Naringenin, non-derivatized, GC-MS Spectrum | splash10-0a4r-2961300000-725a9d843a4286e86b06 | Spectrum | GC-MS | (S)-Naringenin, non-derivatized, GC-MS Spectrum | splash10-00fs-1951400000-0e93ea96a72cb2a5a868 | Spectrum | GC-MS | (S)-Naringenin, non-derivatized, GC-MS Spectrum | splash10-0a4r-2961300000-725a9d843a4286e86b06 | Spectrum | GC-MS | (S)-Naringenin, non-derivatized, GC-MS Spectrum | splash10-00fs-1951400000-44c9c035aeffcacf4e8c | Spectrum | GC-MS | (S)-Naringenin, non-derivatized, GC-MS Spectrum | splash10-004l-1931100000-ec4d00bbd2895d4d5f9c | Spectrum | GC-MS | (S)-Naringenin, non-derivatized, GC-MS Spectrum | splash10-0a4r-2961300000-6cd5d798a9dad326f771 | Spectrum | Predicted GC-MS | (S)-Naringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-006x-1290000000-3182db290eb43c661919 | Spectrum | Predicted GC-MS | (S)-Naringenin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01b9-2531900000-0583af94457df8aad759 | Spectrum | Predicted GC-MS | (S)-Naringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (S)-Naringenin, 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 - Quattro_QQQ 10V, Negative (Annotated) | splash10-00di-0190000000-ba73aef4d7cf20a2777d | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-066r-3900000000-98ba56d82461a2dc7f6f | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-02t9-9600000000-005d5eb55c1f6f3b893d | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive | splash10-00di-0090000000-87dba9fe511299bf27e8 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive | splash10-00di-0090000000-52282430f89f3cfd51ff | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0g4i-1960000000-74e384d175dd4f05938c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-014i-1900000000-702ce5f0315e56bb08a0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-2900000000-aeb81b324d8162537df3 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0fk9-1960000000-b4a541e5476f88624522 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-000i-0090000000-cfa015b97699d9b8d3a9 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 25V, Negative | splash10-0gb9-0900000000-5295f7ce31d20a80235c | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0gb9-0900000000-5295f7ce31d20a80235c | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0gb9-0900000000-5295f7ce31d20a80235c | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0gb9-0900000000-5295f7ce31d20a80235c | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0gb9-0900000000-5295f7ce31d20a80235c | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0gb9-0900000000-5295f7ce31d20a80235c | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-00di-0090000000-dae76236c5699dabc079 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 25V, Negative | splash10-0gb9-0900000000-5295f7ce31d20a80235c | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-00di-0090010000-5e9a02398f13b71eccfb | 2017-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0290000000-32844ab19a143b70951b | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fk9-0980000000-93073e4c39e23c3099c5 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uki-4900000000-8d2daa4eb7a40b866718 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-b29e35ecf9be0aa440c2 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-1390000000-e9112df7c7b29664a011 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014l-6920000000-3b7e4e282dc4008e8c8e | 2017-07-26 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 388383 |
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ChEMBL ID | CHEMBL9352 |
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KEGG Compound ID | C00509 |
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Pubchem Compound ID | 439246 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17846 |
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Phenol-Explorer ID | 201 |
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DrugBank ID | DB03467 |
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HMDB ID | HMDB02670 |
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CRC / DFC (Dictionary of Food Compounds) ID | BFM77-B:BFM78-C |
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EAFUS ID | Not Available |
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Dr. Duke ID | NARINGENIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000982 |
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HET ID | NAR |
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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 | Naringenin |
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Phenol-Explorer Metabolite ID | 201 |
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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 | Descriptor | ID | Definition | Reference |
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11beta-hydroxysteroid-dehydrogenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | anti acetylcholinesterase | 38462 | An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. | DUKE | anti aflatoxin | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | anti aggregant | | | DUKE | anti Alzheimeran | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti amnesic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti amyloid-beta | | | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti escherichic | | | DUKE | anti estrogenic | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | anti fibrotic | | | DUKE | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti HIV | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti mutagenic | | | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti peristaltic | | | DUKE | anti peroxidative | | | DUKE | anti radicular | | | DUKE | anti sindhis | | | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti staphylococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | antitumor promoter | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | aphidifuge | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | aromatase inhibitor | 50790 | An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones. | DUKE | cAMP-phosphodiesterase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | candidicide | | | DUKE | choleretic | | | DUKE | cytochrome-P450 inhibitor | 50183 | An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances. | DUKE | decarboxylase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | embryotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | estrogenic | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | fungistat | | | DUKE | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | neuroprotective | 63726 | Any compound that can be used for the treatment of neurodegenerative disorders. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | serotonin inhibitor | 48279 | Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists. | DUKE | teratogenic | 50905 | A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. | DUKE | TNF-alpha inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | topoisomerase-I inhibitor | 50276 | A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA. | DUKE | utero trophic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE |
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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 | show |
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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 | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — 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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