Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-02-24 19:10:37 UTC
Primary IDFDB002775
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAesculetin
DescriptionAesculetin, 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 Number305-01-1
Structure
Thumb
Synonyms
SynonymSource
6,7-Dihydroxy-2H-1-benzopyran-2-oneChEBI
6,7-DihydroxycoumarinChEBI
CichorigeninChEBI
Cichoriin agluconChEBI
Cichoriin aglyconChEBI
Esculin agluconChEBI
Esculin aglyconChEBI
2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9ci)HMDB
6,7-Dihydroxy-2-benzopyroneHMDB
6,7-Dihydroxy-2H-chromen-2-oneHMDB
6,7-Dihydroxy-coumarinHMDB
6,7-Dihydroxycoumarin, 8ciHMDB
Aesculetin (cichorigeninHMDB
AsculetineHMDB
Coumarin, 6,7-dihydroxy- esculetinHMDB
EsculetinHMDB
EsculetolHMDB
Esculetol)HMDB
AesculetinChEBI
2H-1-Benzopyran-2-one, 6,7-dihydroxy-biospider
2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9CI)biospider
6,7-Dihydroxycoumarin, 8CIdb_source
CichorIIn agluconbiospider
CichorIIn aglyconbiospider
Coumarin, 6, 7-dihydroxy-biospider
Coumarin, 6,7-dihydroxy-biospider
Coumarin, 6,7-dihydroxy- Esculetinbiospider
Esculatinbiospider
esculetol)biospider
Predicted Properties
PropertyValueSource
Water Solubility4.6 g/LALOGPS
logP1.38ALOGPS
logP1.18ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.91ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.51 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H6O4
IUPAC name6,7-dihydroxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
InChI KeyILEDWLMCKZNDJK-UHFFFAOYSA-N
Isomeric SMILESOC1=C(O)C=C2C=CC(=O)OC2=C1
Average Molecular Weight178.143
Monoisotopic Molecular Weight178.026608673
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent6,7-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.68%; H 3.39%; O 35.92%DFC
Melting PointMp 270°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data353 (e 12000) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-6900000000-7b2a54b680eb0245558a2015-03-01View Spectrum
GC-MSAesculetin, non-derivatized, GC-MS Spectrumsplash10-004i-7900000000-22e400291639a7bbb33aSpectrum
GC-MSAesculetin, non-derivatized, GC-MS Spectrumsplash10-004i-7900000000-22e400291639a7bbb33aSpectrum
Predicted GC-MSAesculetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f7k-0900000000-27f017ab7c2ce7d51594Spectrum
Predicted GC-MSAesculetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4091000000-75f069a0c45a2105bec7Spectrum
Predicted GC-MSAesculetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-099787543429855740d52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-7463290884843ecedfcd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0561-0900000000-51a6f720320ed2c06bad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-293c319b48c0eef0fc1f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-1900000000-c1c544e7e6908455b35a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-055r-9600000000-ab9e766b7e2e6ca68e242017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-55055a28076339d9e00c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-057i-0900000000-f1f7d3c5c646263fec5a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-b32d205aa8377f348f322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-c52a5a89a2694dc97b3f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-84537a7c4f55946e68142017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-6fd1fa0c3284283918962017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-01cff2483b03717e8be32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-df8ba2ed269c599a34fd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fr-1900000000-27b50b8924af5378d7b02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-6e66bee9ed2657fcd00a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-1900000000-55cc4447de7427b3e5e02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-1b218d16bdf44f9f7e042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-0900000000-f445625d24b1436ba21e2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-96b92caac30fde152f752016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d2c3a55e9c5410dcf2c62016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-4900000000-3333d8cac0ad0cd849dd2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-584e96c31f961d05b6d72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-5abbabd3e97d0592e3692016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-bc43365ec40caf4ed6e92016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID4444764
ChEMBL IDCHEMBL244743
KEGG Compound IDC09263
Pubchem Compound ID5281416
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID639
DrugBank IDNot Available
HMDB IDHMDB30819
CRC / DFC (Dictionary of Food Compounds) IDCNP29-S:CNP29-S
EAFUS IDNot Available
Dr. Duke IDESCULETIN|AESCULETIN
BIGG IDNot Available
KNApSAcK IDC00002471
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-lipoxygenase inhibitor23924 An agent that blocks the activity of 5-lipoxygenase, an enzyme involved in leukotriene production, reducing inflammation and allergic responses. Therapeutically, it's used to treat asthma, allergies, and inflammatory disorders, such as arthritis, by inhibiting the synthesis of pro-inflammatory leukotrienes.DUKE
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti-arrhythmic38070 An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia.DUKE
Anti-asthmatic49167 An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.DUKE
Anti bacterial33282 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 capillary-fragilityAn agent that strengthens capillary walls to prevent rupture, reducing bruising and bleeding. It plays a biological role in maintaining vascular integrity, and has therapeutic applications in treating conditions like purpura and hemorrhoids, with key medical uses in preventing and managing microvascular damage.DUKE
Anti dysenteric52217 An agent that treats and prevents dysentery, reducing inflammation and diarrhea. It is used to manage bacterial, viral, or parasitic infections, and is commonly applied in treating gastrointestinal disorders, such as amoebic dysentery, and other intestinal infections.DUKE
Anti-escherichicAn antibody binding to Escherichia-specific targets, playing a role in immune defense. Therapeutically, it is used to combat E. coli infections, with key medical applications in treating urinary tract infections, sepsis, and gastrointestinal diseases.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti pyretic35493 An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.DUKE
Cancer preventive35610 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
Cardiodepressant38070 An agent that slows heart rate and reduces cardiac contractility, used to manage conditions like hypertension, angina, and arrhythmias, reducing the heart's workload and oxygen demand.DUKE
CholereticAn agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.DUKE
Cosmetic64857 A substance used to enhance physical appearance, with no therapeutic effect. It plays a social and psychological role, boosting self-esteem and confidence. Key uses include skincare, haircare, and makeup, with no direct medical applications, but can have indirect benefits such as improving mental well-being.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
DermatitigenicAn agent that causes inflammation of the skin (dermatitis), triggering allergic reactions and immune responses. Its biological role involves activating immune cells, leading to skin irritation. Therapeutically, it is used to test skin sensitivity and develop treatments for dermatitis. Key medical uses include diagnosing skin allergies and researching dermatitis treatments.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Hepatoprotective62868 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
HypertensiveAn agent that increases blood pressure, used therapeutically to treat hypotension (low blood pressure) and shock, and medically to manage conditions such as orthostatic hypotension and postural hypotension.DUKE
Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.DUKE
MusculotropicAn agent that acts on muscle tissue, stimulating muscle activity and contraction. It plays a biological role in regulating muscle tone and movement. Therapeutically, musculotropic agents are used to treat muscle weakness, paralysis, and atrophy, with key medical applications in neurology and physical medicine.DUKE
MyorelaxantAn agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.DUKE
Pesticide25944 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
Prostaglandin synthesis inhibitor35222 An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs).DUKE
Sunscreen52217 A topical agent that blocks UV radiation, preventing skin damage and reducing the risk of skin cancer. Its therapeutic applications include protection against sunburn, photoaging, and photodermatoses. Key medical uses include prevention of melanoma, basal cell carcinoma, and squamous cell carcinoma, as well as management of photosensitive disorders.DUKE
UV-screen52217 An agent that absorbs or blocks ultraviolet (UV) radiation, preventing skin damage and reducing risk of skin cancer. It plays a biological role in protecting skin from UV-induced harm. Therapeutically, UV-screens are used to prevent sunburn, photoaging, and skin cancer, with key medical applications in dermatology and preventive care.DUKE
Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.DUKE
Anti-oxidant22586 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot 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.