Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:28 UTC |
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Update date | 2019-11-26 02:57:48 UTC |
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Primary ID | FDB002677 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Hesperetin |
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Description | Isolated from Mentha (peppermint) and numerous Citrussubspecies, with lemons, tangerines and oranges being especially good sources. Nutriceutical with anti-cancer props. Glycosides also widely distributed
Hesperetin is a bioflavonoid and, to be more specific, a flavanone. Hesperidin (a flavonone glycoside) is water soluble due to the presence of the sugar part in its structure, so on ingestion it releases its aglycone i.e: hesperetin. Hesperidin is found in Citrus fruits.; Hesperetin is a cholesterol lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions. Hesperetin is also a biomarker for the consumption of citrus fruits. |
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CAS Number | 520-33-2 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-(S)-Hesperetin | ChEBI | (-)-Hesperetin | ChEBI | (2S)-Hesperetin | ChEBI | (S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one | ChEBI | 3',5,7-Trihydroxy-4'-methoxyflavanone | ChEBI | Hesperitin | MeSH | 5,7, 3'-Trihydroxy-4'-methoxyflavanone | HMDB | 5,7,3'-Trihydroxy-4'-methoxyflavanone | HMDB | Cyanidanon 4'-methyl ether 1626 | HMDB | Hesperin | HMDB | Prestwick_908 | HMDB | YSO2 | HMDB | (S)-2,3-dihydro-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one | ChEBI | (S)-Hesperetin | manual | S-3',5,7-Trihydroxy-4'-methoxyflavanone | biospider | S-5,7,3'-Trihydroxy-4'-methoxyflavanone | biospider |
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Predicted Properties | |
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Chemical Formula | C16H14O6 |
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IUPAC name | (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one |
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InChI Identifier | InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 |
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InChI Key | AIONOLUJZLIMTK-AWEZNQCLSA-N |
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Isomeric SMILES | COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1 |
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Average Molecular Weight | 302.2788 |
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Monoisotopic Molecular Weight | 302.07903818 |
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Classification |
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Description | Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. |
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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 | O-methylated flavonoids |
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Direct Parent | 4'-O-methylated flavonoids |
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Alternative Parents | |
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Substituents | - 4p-methoxyflavonoid-skeleton
- Flavanone
- Hydroxyflavonoid
- 7-hydroxyflavonoid
- 5-hydroxyflavonoid
- 3'-hydroxyflavonoid
- Flavan
- Chromone
- Chromane
- Benzopyran
- Methoxyphenol
- 1-benzopyran
- Methoxybenzene
- Phenoxy compound
- Aryl alkyl ketone
- Anisole
- Phenol ether
- Aryl ketone
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Vinylogous acid
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxide
- Organic oxygen compound
- 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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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Foods | Fruits and vegetables: |
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Physico-Chemical Properties |
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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 63.57%; H 4.67%; O 31.76% | DFC |
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Melting Point | Mp 228-230° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 2.60 | 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 -37.6 (c, 1.8 in EtOH) | 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 | Hesperetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-0792000000-043d1ca82d4702349341 | Spectrum | Predicted GC-MS | Hesperetin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udj-3860980000-a1715e067e13bbdada3e | Spectrum | Predicted GC-MS | Hesperetin, 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 10V, Negative | splash10-0udi-0009000000-da94c45c0a6bde515ea3 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0udi-0169000000-5d9b7fba914d229018a6 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-053i-0920000000-b6ab2fed21176a341b28 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0udi-0009000000-b833c4c244a2461530ec | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0udi-0009000000-32f8b49c4bc1df10782a | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0iki-0930000000-20176d350f94ae4a84ed | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0udi-2910000000-54a5cf5acd3ca156389e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0009000000-2a5462077f9208908972 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0139000000-0c743a741d25379011aa | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0w2i-0961000000-8406f0210238c955e23e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0gw0-0920000000-b833f9a80eb4ea8d3b13 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-052r-0910000000-943c442894f2e6d36fe3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0zfr-0925000000-20d9733844b315a5aac1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0f7c-0092000000-df166f951c1d37996e32 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0f79-0092000000-28f5918da43818b380bf | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0009000000-fda4f743655d07e229dd | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0ufr-0906000000-4ff368578ae1225967b0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0ufr-0900000000-aaca372b112b1730d913 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0900000000-8857224e3cadbbf71a7d | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0329000000-4364410cdc5a65b92032 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udr-0944000000-edd7b755d11b9331e6c9 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uki-3910000000-9e449d46da8305c0b794 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0109000000-21473197ac3beced4628 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0569000000-1e4d2574c341d9d9124f | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pbl-4940000000-c9a717aa36bf4402e6c7 | 2017-07-26 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 65234 |
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ChEMBL ID | CHEMBL399121 |
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KEGG Compound ID | C01709 |
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Pubchem Compound ID | 72281 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 203 |
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DrugBank ID | DB01094 |
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HMDB ID | HMDB05782 |
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CRC / DFC (Dictionary of Food Compounds) ID | CNB06-R:CNB07-S |
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EAFUS ID | 934 |
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Dr. Duke ID | HESPERETIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000968 |
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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 | Hesperetin |
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Phenol-Explorer Metabolite ID | 203 |
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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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Anti bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | Anti feedant | | A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage. | DUKE | Anti lipolytic | | An agent that prevents the breakdown of lipids, playing a biological role in regulating fat metabolism. Therapeutically, it is used to manage conditions like hypertriglyceridemia and diabetic ketoacidosis, with key medical applications in lipid disorders and cardiovascular disease prevention. | DUKE | Anti-viral | 22587 | An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Fungistat | | An agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients. | DUKE | Hepatoprotective | 62868 | An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | CHEBI |
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Enzymes | Name | Gene Name | UniProt ID |
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Sterol O-acyltransferase 1 | SOAT1 | P35610 |
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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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