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Record Information
Version1.0
Created at2012-09-11 17:39:14 UTC
Updated at2024-04-19 10:08:37 UTC
NP-MRD IDNP0000027
Secondary Accession NumbersNone
Natural Product Identification
Common 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 sherries. Aesculetin has also been detected, but not quantified, in several different foods, such as horseradish, carrots, dandelions, grape wines, and highbush blueberries. This could make aesculetin a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC9H6O4
Average Mass178.1430 Da
Monoisotopic Mass178.02661 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number305-01-1
SMILESNot Available
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 KeyILEDWLMCKZNDJK-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea filipendulina
Achillea grandifolia
Aesculus hippocastanumPlant
Aesculus turbinataPlant
Allium ampeloprasumFooDB
Aloe arborescens
Althaea officinalis
Anethum graveolensFooDB
Anisodus tanguticusPlant
Anthriscus cerefolium
Arabidopsis thaliana
Arachis hypogaeaFooDB
Aralia fargesiiPlant
Armoracia rusticanaFooDB
Artemisia capillaris
Artemisia dracunculusFooDB
Artemisia eriopoda
Artemisia jacutica
Artemisia mongolica
Artemisia montana
Artemisia tridentata
Artemisia vulgarisFooDB
Artemisia xerophytica
Asphodeline damascena
Asphodeline globiferaPlant
Berberis vulgaris
Bidens tripartitaPlant
Bupleurum fruticosum
Cacalia hastata
Calendula officinalis
Campanula rotundifolia
Caragana frutex
Cedrelopsis grevei
Ceratostigma willmottianumPlant
Chondrilla juncea
Chrysanthemum segetum
Cichorium glandulosum
Cichorium intybusFooDB
Cichorium pumilum
Citrus limonPlant
Citrus limoniaPlant
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dictamnus albus
Erica vagansPlant
Euphorbia decipiens
Euphorbia lagascae
Euphorbia lanataPlant
Euphorbia lathyrisPlant
Euphorbia lunulataPlant
Euphorbia petiolata
Fraxinus angustifolia
Fraxinus bungeanaPlant
Fraxinus chinensisPlant
Fraxinus excelsior
Fraxinus floribunda
Fraxinus insularis
Fraxinus mandshuricaPlant
Fraxinus ornusPlant
Fraxinus paxianaPlant
Fraxinus rhynchophyllaPlant
Fraxinus spp.Plant
Fraxinus stylosaPlant
Fraxinus szaboanaPlant
Galinsoga quadriradiata
Geum rivale
Ginkgo bilobaPlant
Gymnophyton isatidicarpum
Haplopappus foliosusPlant
Haplopappus multifolius
Helichrysum italicum
Helichrysum maracandicum
Hordeum vulgareFooDB
Hydrophyllum virginianum
Hylotelephium ewersii
Isodon eriocalyx
Ixeridium laevigatum
Khaya ivorensisPlant
Khaya senegalensis L.Plant
Koelpinia linearisPlant
Lepidaploa remotiflora
Ligularia amplexicaulis
Ligularia sagitta
Ligustrum japonicum
Lonicera bournei Hemsl.
Lonicera gracilipes var. glandulosaPlant
Lupinus angustifolius
Manihot esculenta
Matricaria chamomilla
Medicago sativaPlant
Meehania urticifoliaPlant
Melilotus suaveolensPlant
Myrtus communis
Nervilia fordii
Notoseris henryi
Notoseris macilenta
Ocimum basilicumFooDB
Ocimum tenuiflorum
Olea europaeaFooDB
Passiflora menispermifolia
Perilla frutescens
Periploca graecaPlant
Phaseolus vulgarisFooDB
Phellodendron amurensePlant
Phellodendron japonicum MAXIMPlant
Potentilla erecta
Prunella vulgaris
Pterocaulon polystachyum
Quercus faginea
Quercus suber
Ranunculus sieboldii
Rhododendron hypoleucum
Rosa laevigata
Salvia euphraticaPlant
Salvia verticillata
Santolina oblongifolia
Scorzonera laciniata
Sedum ewersiiPlant
Sedum kamtschaticumPlant
Sedum selskianum
Skimmia laureola
Solanum dasyphyllum
Solanum virginianumPlant
Sonchus asper
Sonchus hierrensis (Pit.) Boulos
Syringa vulgaris
Tagetes lucida
Taraxacum formosanumPlant
Taraxacum mongolicum
Taraxacum officinaleFooDB
Theobroma cacaoFooDB
Trifolium pratensePlant
Vaccinium corymbosumFooDB
Viburnum cylindricum
Vicia sativa
Viola mandshurica
Vitis vinifera
Withania somnifera
Xenophyllum dactylophyllum
Zanthoxylum piasezkii
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
HMDB IDHMDB0030819
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002775
KNApSAcK IDC00002471
Chemspider ID4444764
KEGG Compound IDC09263
BioCyc IDCPD-8097
BiGG IDNot Available
Wikipedia LinkAesculetin
METLIN IDNot Available
PubChem Compound5281416
PDB IDNot Available
ChEBI ID490095
Good Scents IDNot Available
References
General References
  1. Ma J, Jones SH, Hecht SM: A coumarin from Mallotus resinosus that mediates DNA cleavage. J Nat Prod. 2004 Sep;67(9):1614-6. doi: 10.1021/np040129c. [PubMed:15387675 ]
  2. Ferrari AM, Sgobba M, Gamberini MC, Rastelli G: Relationship between quantum-chemical descriptors of proton dissociation and experimental acidity constants of various hydroxylated coumarins. Identification of the biologically active species for xanthine oxidase inhibition. Eur J Med Chem. 2007 Jul;42(7):1028-31. doi: 10.1016/j.ejmech.2006.12.023. Epub 2007 Jan 13. [PubMed:17316915 ]
  3. Riveiro ME, Moglioni A, Vazquez R, Gomez N, Facorro G, Piehl L, de Celis ER, Shayo C, Davio C: Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells. Bioorg Med Chem. 2008 Mar 1;16(5):2665-75. doi: 10.1016/j.bmc.2007.11.038. Epub 2007 Nov 19. [PubMed:18060791 ]
  4. Park C, Jin CY, Kwon HJ, Hwang HJ, Kim GY, Choi IW, Kwon TK, Kim BW, Kim WJ, Choi YH: Induction of apoptosis by esculetin in human leukemia U937 cells: roles of Bcl-2 and extracellular-regulated kinase signaling. Toxicol In Vitro. 2010 Mar;24(2):486-94. doi: 10.1016/j.tiv.2009.09.017. Epub 2009 Sep 26. [PubMed:19786087 ]
  5. Witaicenis A, Seito LN, Di Stasi LC: Intestinal anti-inflammatory activity of esculetin and 4-methylesculetin in the trinitrobenzenesulphonic acid model of rat colitis. Chem Biol Interact. 2010 Jul 30;186(2):211-8. doi: 10.1016/j.cbi.2010.03.045. Epub 2010 Apr 7. [PubMed:20380826 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .