Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-02-24 19:10:37 UTC
Primary IDFDB002776
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAesculin
DescriptionAesculin belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Aesculin is an extremely weak basic (essentially neutral) compound (based on its pKa). Aesculin is found, on average, in the highest concentration within beers. Aesculin has also been detected, but not quantified in, several different foods, such as lentils, sweet basils, mugworts, common beans, and chicories. This could make aesculin a potential biomarker for the consumption of these foods.
CAS Number531-75-9
Structure
Thumb
Synonyms
SynonymSource
6,7-Dihydroxycoumarin 6-glucosideHMDB
BicolorinHMDB
CrataeginHMDB
EnallachromeHMDB
EscosylHMDB
Esculetin 6-b-D-glucosideHMDB
Esculetin 6-beta-D-glucosideHMDB
Esculetin 6-O-glucosideHMDB
EsculinHMDB
EsculineHMDB
EsculosideHMDB
PolychromHMDB
PolychromeHMDB
Vitamin C2HMDB
Aesculindb_source
Esculetin 6-β-D-glucosidebiospider
Predicted Properties
PropertyValueSource
Water Solubility10.3 g/LALOGPS
logP-0.53ALOGPS
logP-1.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.12ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.65 m³·mol⁻¹ChemAxon
Polarizability31.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H16O9
IUPAC name7-hydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
InChI IdentifierInChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2
InChI KeyXHCADAYNFIFUHF-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=C(O)C=C3OC(=O)C=CC3=C2)C(O)C(O)C1O
Average Molecular Weight340.2821
Monoisotopic Molecular Weight340.07943211
Classification
Description Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassCoumarin glycosides
Direct ParentCoumarin glycosides
Alternative Parents
Substituents
  • Coumarin o-glycoside
  • Coumarin-6-o-glycoside
  • Phenolic glycoside
  • 7-hydroxycoumarin
  • Hydroxycoumarin
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • 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 52.95%; H 4.74%; O 42.32%DFC
Melting PointMp 205°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -77.5 (c, 3 in aq. dioxan)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAesculin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6947000000-19895b8b387f11d9179dSpectrum
Predicted GC-MSAesculin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2353029000-f90429c99944a173ba08Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002r-0809000000-a156a991511f00b65a772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-900b94103dde5ea786f42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-dead96eade01b822e1022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-d1089ced80e3aad1409b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-fd6b0737193a9669d0eb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00c0-0900000000-80c75412526e8c4c38392017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0906000000-68762b523b2407ebaa2f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-9a0d97a2a3f118d39d432015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-81ab23ab5df41a41c8da2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1729000000-b928bdec44f5d1346b352015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1911000000-16d7b3b8f15dd797da5c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-2900000000-46bb89536fc947bc66302015-04-25View Spectrum
NMRNot Available
ChemSpider ID4508522
ChEMBL IDNot Available
KEGG Compound IDC09264
Pubchem Compound ID5351506
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID640
DrugBank IDNot Available
HMDB IDHMDB30820
CRC / DFC (Dictionary of Food Compounds) IDCNP29-S:CNP31-N
EAFUS IDNot Available
Dr. Duke IDESCULIN|AESCULOSIDE|AESCULIN
BIGG IDNot Available
KNApSAcK IDC00002472
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAesculin
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
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 acrocyanotic52217 An agent that improves blood flow to the extremities, reducing discoloration and pain in hands and feet. It has a biological role in vasodilation, therapeutic applications in treating peripheral vascular diseases, and key medical uses in managing conditions like Raynaud's disease and acrocyanosis.DUKE
Anti-aging52217 An agent that slows or reverses cellular aging, promoting youthful function. Its biological role involves protecting against oxidative stress and DNA damage. Therapeutically, it has applications in dermatology, gerontology, and regenerative medicine, with key medical uses including skin rejuvenation, reducing age-related diseases, and improving overall healthspan.DUKE
Anti-alopecic52217 An agent that promotes hair growth and prevents hair loss, commonly used to treat alopecia and other hair-related disorders, by inhibiting dihydrotestosterone (DHT) and stimulating hair follicle growth.DUKE
Anti-arthritic52217 An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.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 cellulitic52217 An agent that reduces the appearance of cellulite, improving skin texture and tone. It enhances blood flow, breaks down fat cells, and strengthens connective tissue, commonly used in cosmetic and dermatological treatments to minimize dimpling and orange peel skin.DUKE
Anti CVSAn agent that counters cardiovascular stress, reducing inflammation and oxidative damage. It has therapeutic applications in managing hypertension, atherosclerosis, and cardiac dysfunction, with key medical uses including prevention of heart failure and stroke.DUKE
Anti dermatitic50177 An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling.DUKE
Anti erythemic50177 An agent that reduces redness of the skin, often used to treat conditions like rosacea and eczema. It plays a biological role in inhibiting inflammation and dilating blood vessels, and has therapeutic applications in dermatology, with key medical uses including topical creams and ointments to alleviate skin redness and irritation.DUKE
Anti-hemorrhoidal52217 An agent that reduces swelling and inflammation of hemorrhoids, commonly used to relieve symptoms of hemorrhoidal disease, such as itching, pain, and bleeding, and to prevent further complications.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.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-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.DUKE
Anti-panniculopathicAn agent that treats Edematous Fibrosclerotic Panniculopathy, reducing persistent subcutaneous fat and skin dimpling associated with cellulite, improving skin texture and appearance.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 Raynaud's52217 An agent that improves blood flow to extremities, reducing vasospasm and relieving symptoms of Raynaud's disease, commonly used to manage cold-induced digital ulcers, pain, and discoloration in fingers and toes.DUKE
Anti-seborrheic52217 An agent that reduces seborrheic dermatitis symptoms, commonly used in managing scalp and skin conditions, such as dandruff, itching, and flaking, by inhibiting fungal growth and inflammation.DUKE
Bacteristat33282 An agent that inhibits bacterial growth, reducing the proliferation of microorganisms without killing them. Therapeutically, bacteristats are used to treat infections, preventing the spread of bacteria and allowing the host's immune system to clear the infection. Key medical uses include treating urinary tract infections, acne, and other bacterial infections where bactericidal agents may not be necessary.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
Cardiotonic38070 An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.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
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.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
MicrovasculokineticAn agent that regulates the motion of microvasculature, the smaller blood vessels. Its biological role involves maintaining blood flow and oxygen delivery to tissues. Therapeutically, it has applications in managing vascular disorders, such as improving circulation and reducing inflammation. Key medical uses include treating conditions like ischemia, hypertension, and peripheral artery disease.DUKE
ParalyticAn agent that induces temporary paralysis or muscle relaxation, used therapeutically to facilitate surgical procedures, manage muscle spasms, and treat conditions like tetanus and seizures, by blocking nerve transmission to muscles.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
Toxic52209 A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.DUKE
VasoprotectiveAn agent that protects and alleviates blood vessel conditions, such as hemorrhoids and varicose veins, by strengthening vessel walls and improving circulation, with therapeutic applications in managing vascular disorders, and key medical uses including hormone replacement therapy with estrogen.DUKE
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).
— 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.