Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:05:31 UTC |
---|
Update date | 2020-02-24 19:10:37 UTC |
---|
Primary ID | FDB002775 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Aesculetin |
---|
Description | Aesculetin, also known as cichorigenin or cichoriin aglucon, belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively. Aesculetin is found, on average, in the highest concentration within sherry. Aesculetin has also been detected, but not quantified in, several different foods, such as mugworts (Artemisia vulgaris), highbush blueberries (Vaccinium corymbosum), grape wine, beer, and opium poppies (Papaver somniferum). This could make aesculetin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Aesculetin. |
---|
CAS Number | 305-01-1 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
6,7-Dihydroxy-2H-1-benzopyran-2-one | ChEBI | 6,7-Dihydroxycoumarin | ChEBI | Cichorigenin | ChEBI | Cichoriin aglucon | ChEBI | Cichoriin aglycon | ChEBI | Esculin aglucon | ChEBI | Esculin aglycon | ChEBI | 2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9ci) | HMDB | 6,7-Dihydroxy-2-benzopyrone | HMDB | 6,7-Dihydroxy-2H-chromen-2-one | HMDB | 6,7-Dihydroxy-coumarin | HMDB | 6,7-Dihydroxycoumarin, 8ci | HMDB | Aesculetin (cichorigenin | HMDB | Asculetine | HMDB | Coumarin, 6,7-dihydroxy- esculetin | HMDB | Esculetin | HMDB | Esculetol | HMDB | Esculetol) | HMDB | Aesculetin | ChEBI | 2H-1-Benzopyran-2-one, 6,7-dihydroxy- | biospider | 2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9CI) | biospider | 6,7-Dihydroxycoumarin, 8CI | db_source | CichorIIn aglucon | biospider | CichorIIn aglycon | biospider | Coumarin, 6, 7-dihydroxy- | biospider | Coumarin, 6,7-dihydroxy- | biospider | Coumarin, 6,7-dihydroxy- Esculetin | biospider | Esculatin | biospider | esculetol) | biospider |
|
---|
Predicted Properties | |
---|
Chemical Formula | C9H6O4 |
---|
IUPAC name | 6,7-dihydroxy-2H-chromen-2-one |
---|
InChI Identifier | InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H |
---|
InChI Key | ILEDWLMCKZNDJK-UHFFFAOYSA-N |
---|
Isomeric SMILES | OC1=C(O)C=C2C=CC(=O)OC2=C1 |
---|
Average Molecular Weight | 178.143 |
---|
Monoisotopic Molecular Weight | 178.026608673 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Coumarins and derivatives |
---|
Sub Class | Hydroxycoumarins |
---|
Direct Parent | 6,7-dihydroxycoumarins |
---|
Alternative Parents | |
---|
Substituents | - 6,7-dihydroxycoumarin
- 7-hydroxycoumarin
- Benzopyran
- 1-benzopyran
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Lactone
- Oxacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Not Available | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 60.68%; H 3.39%; O 35.92% | DFC |
---|
Melting Point | Mp 270° | 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 | Not Available | |
---|
Spectroscopic UV Data | 353 (e 12000) (MeOH) (Berdy) | DFC |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
EI-MS | Mass Spectrum (Electron Ionization) | splash10-004i-6900000000-7b2a54b680eb0245558a | 2015-03-01 | View Spectrum | GC-MS | Aesculetin, non-derivatized, GC-MS Spectrum | splash10-004i-7900000000-22e400291639a7bbb33a | Spectrum | GC-MS | Aesculetin, non-derivatized, GC-MS Spectrum | splash10-004i-7900000000-22e400291639a7bbb33a | Spectrum | Predicted GC-MS | Aesculetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f7k-0900000000-27f017ab7c2ce7d51594 | Spectrum | Predicted GC-MS | Aesculetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-4091000000-75f069a0c45a2105bec7 | Spectrum | Predicted GC-MS | Aesculetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-0900000000-099787543429855740d5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-0900000000-7463290884843ecedfcd | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0561-0900000000-51a6f720320ed2c06bad | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-293c319b48c0eef0fc1f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-1900000000-c1c544e7e6908455b35a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-055r-9600000000-ab9e766b7e2e6ca68e24 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-0900000000-55055a28076339d9e00c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-057i-0900000000-f1f7d3c5c646263fec5a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0059-0900000000-b32d205aa8377f348f32 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0059-0900000000-c52a5a89a2694dc97b3f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-0900000000-84537a7c4f55946e6814 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-0900000000-6fd1fa0c328428391896 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0900000000-01cff2483b03717e8be3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0900000000-df8ba2ed269c599a34fd | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-05fr-1900000000-27b50b8924af5378d7b0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-6e66bee9ed2657fcd00a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-1900000000-55cc4447de7427b3e5e0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-0900000000-1b218d16bdf44f9f7e04 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00e9-0900000000-f445625d24b1436ba21e | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-96b92caac30fde152f75 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0900000000-d2c3a55e9c5410dcf2c6 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4r-4900000000-3333d8cac0ad0cd849dd | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-584e96c31f961d05b6d7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0900000000-5abbabd3e97d0592e369 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-4900000000-bc43365ec40caf4ed6e9 | 2016-08-03 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | 4444764 |
---|
ChEMBL ID | CHEMBL244743 |
---|
KEGG Compound ID | C09263 |
---|
Pubchem Compound ID | 5281416 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | 639 |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB30819 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | CNP29-S:CNP29-S |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | ESCULETIN|AESCULETIN |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00002471 |
---|
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 | Not Available |
---|
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 | Descriptor | ID | Definition | Reference |
---|
5-lipoxygenase 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 | analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | anti arrhythmic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | anti asthmatic | 49167 | A drug used to treat asthma. | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti capillary-fragility | | | DUKE | anti dysenteric | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti escherichic | | | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti mutagenic | | | DUKE | anti pyretic | 35493 | A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever. | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti staphylococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | cardiodepressant | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | choleretic | | | DUKE | cosmetic | 64857 | The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it. | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | dermatitigenic | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | hypertensive | | | DUKE | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | DUKE | musculotropic | | | DUKE | myorelaxant | | | 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 | prostaglandin synthesis inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | sunscreen | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | UV-screen | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | xanthine oxidase inhibitor | 35634 | An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2). | 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. | CHEBI |
|
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
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. — 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.
|
---|