Aesculin

Esculin

HCID 5281417CAS 531-75-9

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

Esculin531-75-9Esculetin 6-O-glucoside6,7-Dihydroxycoumarin 6-glucosideEsculetin 6-beta-D-glucoside6,7-Dihydroxycoumarin-6-O-glucoside7-Hydroxy-6-cumarinyl-glucosidDTXSID70453186-(beta-D-Glucopyranosyloxy)-7-hydroxy-cumarin1Y1L18LQAFCHEBI:4853NSC-26665
Weitere Namen anzeigen
EsculineEscosylBICOLOINAESCULINPOLYDROMBicolorinCrataeginPolychromvitaminc2
DTXCID50253187-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one7-hydroxy-2-oxo-2H-chromen-6-yl beta-D-glucopyranoside2H-1-Benzopyran-2-one, 6-(beta-D-glucopyranosyloxy)-7-hydroxy-7-hydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-2-oneRefChem:35731208-517-5686-183-3

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

Experimentelle und physikochemische Eigenschaften

Melting Point205 °C
Physical DescriptionSolid
Collision Cross Section · 2 Einträge

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 3 Einträge

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 · 2 Einträge

Not Classified

Not Classified

Regulatorische Informationen

Regulatory Information · 3 Einträge

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

Chemie und Industrie

Pharmakologische Informationen

PharmacodynamicsTopically applied Esculine increases the “capillary density” (the number of capillaries open to flow per surface unit) and improves the morphological aspect of the smallest blood vessels.
Mechanism of Action · 1 Eintrag

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.

Biological Half-LifeAbsorption half life about 1 hour and elimination half life about 20 hours
Metabolism/Metabolites · 1 Eintrag

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.

Absorption, Distribution and ExcretionRarely, absorbed into the blood stream if used as a combination with other ingredients in suppository form. But, Applying cream or ointment form to open wound or skin may lead this drug to absorb and circulate into blood stream.
Cellular LocationsCytoplasm;Extracellular

Verwendung und Herstellung

Use ClassificationCosmetics -> Tonic
General Manufacturing Information2H-1-Benzopyran-2-one, 6-(.beta.-D-glucopyranosyloxy)-7-hydroxy-: ACTIVE

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

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A hydroxycoumarin that is the 6-O-beta-D-glucoside of esculetin.

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