Grundinformationen
- Standard-SMILES
O=c1ccc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc2o1- InChIKey
XHCADAYNFIFUHF-TVKJYDDYSA-N- Summenformel
- C15H16O9
- Durchschnittliche Molmasse
- 340,28 g/mol
- Monoisotopische Masse
- 340,07943208
Namen und Bezeichner
- Bevorzugter Name
- Esculin
- IUPAC
- 7-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
- Lokaler Name
- Aesculin
- Englischer Name
- Esculin
- Summenformel
- C15H16O9
- Molmasse
- 340.28
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
531-75-9- PubChem CID
- 5281417
- DTXSID
DTXSID7045318- ChEMBL
CHEMBL482581- ChEBI
CHEBI:4853- UNII
- 1Y1L18LQAF
- EC Number
- 208-517-5、686-504-7
- Nikkaji
- J6.981G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,6
- Polarare Oberfläche (TPSA)
- 146 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 495
Experimentelle und physikochemische Eigenschaften
Collision Cross Section
174 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
193.73 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];182.53 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];164.77 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];172.99 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 203 °C · 203 °C
- Siedepunkt
- 396.1 °C · 396.1°C (rough estimate)
- Dichte
- 0.791 g/mL · 0.791 g/mL at 20 °C
- Dampfdruck
- 0 Pa · 0Pa at 25℃
- Brechungsindex
- -79 ° · -79 ° (C=2.4, 50% Dioxane)
- Flammpunkt
- 15 °C · 15 °C
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 50 mg/mL · methanol: 50 mg/mL hot, clear to very faintly turbid, yellow-green fluoresc.
- pka
- 7 · 7.00±0.20(Predicted)
- Aggregatzustand
- Liquid
- Farbe
- Clear
- Wasserlöslichkeit
- MODERATELY SOLUBLE
- Merck
- 3698 · 3698
- Stabilität
- Stable. Incompatible with strong oxidizing agents.
- Kosmetik-Inhaltsstoffe Funktionen
- TONICLIGHT STABILIZER
- InChI
- 1S/C15H16O9.H2O/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;1H2/t10-,12-,13+,14-,15-;/m1./s1
- InChIKey
- YRABYCJKUBFWQY-FHXAZYNBSA-N
- SMILES
- O.OC[C@H]1O[C@@H](Oc2cc3C=CC(=O)Oc3cc2O)[C@H](O)[C@@H](O)[C@@H]1O || O.OC[C@H]1O[C@@H](Oc2cc3C=CC(=O)Oc3cc2O)[C@H](O)[C@@H](O)[C@@H]1O
- LogP
- -1.307 · -1.307 (est)
- CAS Datenbank
- 531 · 531-75-9(CAS DataBase Reference)
- NIST chemische Informationen
- 7 · 7-Hydroxy-2-oxo-2h-chromen-6-yl hexopyranoside(531-75-9)
- EPA chemische Informationen
- Esculin (531-75-9)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (137 of 137) of all reports.
Not Classified;Reported as not meeting GHS hazard criteria by 137 of 137 companies. For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 137 reports by companies from 1 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 137 of 137 reports by companies.;There are 0 notifications provided by 0 of 137 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Not Classified;Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Regulatory Information
Chemical: 2H-1-Benzopyran-2-one, 6-(.beta.-D-glucopyranosyloxy)-7-hydroxy-
Status: Active Update: 12-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25090
2H-1-Benzopyran-2-one, 6-(.beta.-D-glucopyranosyloxy)-7-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Not Classified
Not Classified
Regulatorische Informationen
Regulatory Information
Chemical: 2H-1-Benzopyran-2-one, 6-(.beta.-D-glucopyranosyloxy)-7-hydroxy-
Status: Active Update: 12-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25090
2H-1-Benzopyran-2-one, 6-(.beta.-D-glucopyranosyloxy)-7-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Sicherheitsdaten
- F
- 3-10-23
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2924 3/PG 2
- hs_code
- 29389090
- RTECS-Nr.
- DJ3085000
- risk_code
- 11-20/21/22-34-68/20/21/22-36/37/38
- hazard_code
- F,C,Xi
- safety_code
- 26-36/37/39-45-24/25-36/37-16
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
The main activities of Esculine focus on capillary protection, as it improves capillary permeability and fragility. It is reported to inhibit catabolic enzymes such as hyaluronidase and collagenase, thus preserving the integrity of the perivascular connective tissue. Esculine also showed good antioxidant properties, protecting triglycerides against auto-oxidation at high temperatures . The antioxidant property might as well explain some of the anti-inflammatory activity of the product, making it a suitable product for after sun treatments, for example.
Metabolism/Metabolites
After oral administration of esculin (100 mg/kg) for rats, plasma, urine, feces and bile samples were collected to screen metabolites. As a result, a total of 19 metabolites (10 phase I metabolites and 9 phase II metabolites) were found and identified. It was also found that after oral administration of esculin, the esculin could be metabolized to esculetin in vivo via deglycosylation, and esculetin was found in all biological samples.
Verwendung und Herstellung
Anwendungen
Verwendenesculin is used as a skin protectant in ointments and creams. This is a glucoside compound originally obtained from the leaves and bark of the horse chestnut tree.
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A hydroxycoumarin that is the 6-O-beta-D-glucoside of esculetin.
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