Compound: Esculetin
SMILES: O=c1oc2c(cc(O)c(c2)O)cc1
InChIKey: ILEDWLMCKZNDJK-UHFFFAOYSA-N
Synonyms: Esculetin, 305-01-1, 6,7-DIHYDROXYCOUMARIN, Aesculetin, 6,7-Dihydroxy-2H-chromen-2-one, Cichorigenin, Cichoriin aglucon, Esculin aglucon, Esculin aglycon, 6,7-dihydroxychromen-2-one, Cichoriin aglycon, 6,7-Dihydroxy-2H-1-benzopyran-2-one, SM2XD6V944, DTXSID3075383, NSC-26428, CHEBI:490095, RefChem:137861, DTXCID5038206, 206-161-5, Esculetol, 2H-1-Benzopyran-2-one, 6,7-dihydroxy-, Esculatin, Asculetine, 6,7-Dihydroxy-2-benzopyrone, 91753-33-2, 2,6-Dihydroxy-7H-chromen-7-one, Coumarin, 6,7-dihydroxy-, MFCD00006874, NSC 26428, 6,7-bis(oxidanyl)chromen-2-one, NSC26428, MLS000069479, CHEMBL244743, 6,7-dihydroxy-1-benzopyran-2-one, Coumarin, 6,7-dihydroxy- Esculetin, Esculetin [Matrix for MALDI-TOF/MS], SMR000059055, 6,7-Dihydroxycoumarin (Esculetin), CCRIS 7065, 6,7-Dihydroxycounmarin, EINECS 206-161-5, BRN 0152788, eculetin, UNII-SM2XD6V944, 6,7-Dihydroxy-2-chromenone, Cichorigenin;, Aesculetin;, Esculetin;, Esculetin CRS, HFC, 6,7-hydroxycoumarin, Esculetin (Standard), Cichorigenin|Aesculetin, Spectrum_001166, Aesculetin (cichorigenin, 6,7-dihydroxy-coumarin, SpecPlus_000334, 6,7-Dihydroxycoumarin;, ESCULETIN [MI], Prestwick0_000940, Prestwick1_000940, Prestwick2_000940, Prestwick3_000940, Spectrum2_000586, Spectrum3_000752, Spectrum4_001886, Spectrum5_000512, bmse000986, Oprea1_719746, SCHEMBL24641, BSPBio_000880, BSPBio_002364, KBioGR_002416, KBioSS_001646, 5-18-03-00202 (Beilstein Handbook Reference), 6,7-Dihydroxycoumarin, 8CI, DivK1c_006430, Esculetin, analytical standard, SPECTRUM1500899, SPBio_000432, SPBio_003049, 6,7-Dihydroxycoumarin, 98%, BPBio1_000968, GTPL5180, orb1305008, orb3140481, SCHEMBL29569228, BDBM34571, cid_5281416, HY-N0284R, KBio1_001374, KBio2_001646, KBio2_004214, KBio2_006782, KBio3_001584, DTXSID801293090, HMS1570L22, HMS1921M14, HMS2097L22, HMS2233G24, HMS3373K09, HMS5083A20, KUC108669N, ALBB-023362, EX-A6796, HY-N0284, Aesculetin (Cichorigenin; Esculetol), BBL037229, CCG-38509, MSK157072, s4711, STL560155, 6,7-Dihydroxy-2H-chromen-2-one #, AKOS000276955, EBC-436057, FE30654, SDCCGMLS-0066669.P001, 2,6-Dihydroxy-7H-1-benzopyran-7-one, SMP2_000093, NCGC00016425-01, NCGC00016425-02, NCGC00016425-03, NCGC00016425-04, NCGC00016425-05, NCGC00016425-06, NCGC00094873-01, NCGC00094873-02, AC-18400, AC-34573, AS-11863, CAS-305-01-1, KSC-11-243-1, NCI60_002119, ST079379, SY036794, DB-014626, AB00489955, CS-0008780, E0386, E1287, NS00004806, C09263, E-3400, O11524, 2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9CI), AE-641/05088017, F241171, SR-01000721907, Q3058018, SR-01000721907-2, BRD-K58149231-001-06-9, BRD-K58149231-001-10-1, B0005-464319, Esculetin, European Pharmacopoeia (EP) Reference Standard, InChI=1/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11
Theoretical properties:
molecular_formula: C9H6O4
molecular_weight: 178.14 g/mol
exact_mass: 178.02660867 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 13
topological_polar_surface_area: 66.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 270 °C
Descriptions:
pubchem: Esculetin is a hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light. It has a role as an antioxidant, an ultraviolet filter and a plant metabolite.
chebi: A  hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.
chembl: ESCULETIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Aesculetin (also known as esculetin, 6,7-dihydroxycoumarin and cichorigenin) is a derivative of coumarin. It is a natural lactone that derives from the intramolecular cyclization of a cinnamic acid derivative.
It is present in chicory and in many toxic and medicinal plants, in form of glycosides and caffeic acid conjugates.
This compound is used in some sunscreens, but there is evidence that it acts as a photosensitizer for DNA damage. The sodium salt of its methyl-derivative is used in dermatology for the treatment of varicose veins.
It is a blue fluorescence compound found in plants. Aesculin, the glucoside of aesculetin, will fluoresce under long wave ultraviolet light (360 nm). The hydrolysis of aesculin results in loss of this fluorescence. Aesculetin has the ability to quench the inner fluorescence of bovine serum albumin.
Aesculetin can be transformed into scopoletin (7-hydroxy-6-methoxycoumarin) and isoscopoletin (6-hydroxy-7-methoxycoumarin) through incubation with rat liver catechol-O-methyltransferase.
Aesculetin can be synthesized by condensation of hydroxyhydroquinone triacetate with malic acid in concentrated sulfuric acid.