HCID5281417

Esculin

7-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one

C15H16O9340.28 g/molCAS 531-75-9

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IDENTITY

结构与身份

标准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
分子式: C15H16O9
平均分子量: 340.28 g/mol
单同位素质量: 340.07943208

COMPUTED

结构计算性质

已同步

XLogP: -0.6
极性表面积: 146 Å²
氢键供体: 5
氢键受体: 9
可旋转键: 3
重原子: 24
形式电荷: 0
复杂度: 495

PROPERTIES

实验与物化性质

Melting Point

205 °C

Physical Description

Solid

Collision Cross Section

174 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

193.73 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；182.53 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；164.77 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；172.99 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

GHS

GHS分类

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.

HAZARDS

危害信息

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

REGULATORY

法规信息

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

PHARMACOLOGY

药理信息

Pharmacodynamics

Topically 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

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-Life

Absorption half life about 1 hour and elimination half life about 20 hours

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.

Absorption, Distribution and Excretion

Rarely, 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 Locations

Cytoplasm；Extracellular

USES

用途与制造

Use Classification

Cosmetics -> Tonic

General Manufacturing Information

2H-1-Benzopyran-2-one, 6-(.beta.-D-glucopyranosyloxy)-7-hydroxy-: ACTIVE

ALIASES

名称与别名

共 123 条

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-26665DTXCID50253187-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

REACTIONS