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Esculin

Esculin structure

CAS No:
531-75-9
Formula:
C15H16O9
Chemical Name:
Esculin
Synonyms:
2H-1-Benzopyran-2-one,6-(β-D-glucopyranosyloxy)-7-hydroxy-;Esculin;6-(β-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one;Crataegin;6,7-Dihydroxycoumarin 6-glucoside;Enallachrome;Escosyl;Esculetin 6-β-D-glucoside;Esculoside;Polychrome;Vitamin C2;Aesculin;Esculine;Polychrom;(-)-Esculin;Esculetin 6-O-glucoside;6-(β-D-Glucopyranosyloxy)-7-hydroxycoumarin;97882-87-6;25360-17-2;28633-38-7;29008-74-0;1078728-35-4
Categories:
Cosmetic Ingredient > Light Stabilizer

Description

Esculin, a fluorescent coumarin glucoside, is an active ingredient of ash bark[1]. Esculin ameliorates cognitive impairment in experimental diabetic nephropathy (DN), and exerts anti‑oxidative stress and anti‑inflammatory effects, via the MAPK signaling pathway[2].

Solid

Esculin is a hydroxycoumarin that is the 6-O-beta-D-glucoside of esculetin. It has a role as an antioxidant and a metabolite. It is a beta-D-glucoside and a hydroxycoumarin. It derives from an esculetin.|Esculin is found in barley. Vitamin C2 is generally considered a bioflavanoid, related to vitamin P esculin is a glucoside that naturally occurs in the horse chestnut (Aesculus hippocastanum), California Buckeye (Aesculus californica) and in daphnin (the dark green resin of Daphne mezereum). Esculin belongs to the family of Glycosyl Compounds. These are carbohydrate derivatives in which a sugar group is bonded through its anmoeric carbonA to another group via a C-, S-,N-,O-, or Se- glycosidic bond.|A derivative of COUMARIN with molecular formula C15H16O9.

Esculin Basic Attributes

Molecular Weight：

340.28

Exact Mass：

340.28

EC Number：

208-517-5

UNII：

1Y1L18LQAF

DSSTox ID：

DTXSID7045318

HScode：

2942000000

Characteristics

PSA：

146

XLogP3：

-0.6

Appearance：

Clear Liquid

Density：

1.7±0.1 g/cm3

Melting Point：

205 °C (decomp)

Boiling Point：

697.7°C at 760 mmHg

Flash Point：

15 °C

Refractive Index：

1.689

Water Solubility：

H2O: MODERATELY soluble ;methanol: 50 mg/mL hot, clear to very faintly turbid, yellow-green fluoresc.

Storage Conditions：

Store at RT.

Specific rotation：

-88 º (c=2,dioxane/water1:1)

Collision Cross Section：

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

Safety Information

Transport codes：

UN 2924 3/PG 2

wgk germany：

hazard class code：

11-20/21/22-34-68/20/21/22-36/37/38

safety instructions：

26-36/37/39-45-24/25-36/37-16

RTECS Number：

DJ3085000

Marks：

F,C,Xi

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Toxicity

Toxicity Summary：

Organism : Mouse Test type : LD50 Route: Intraperitoneal Reported dose: 1900mg/kg No reported effects known other than LD50

Drug Information

Drug Indication：

As medication, esculin is sometimes used as a vasoprotective agent. Esculin is also used in a microbiology laboratory to aid in the identification of bacterial species (especially Enterococci and Listeria), as all strains of Group D Streptococci hydrolyze æsculin in 40% bile.

Pharmacology：

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.

Absorption：

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.

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.

Biological Half-Life：

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

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.

MeSH Entry Terms：

Aesculin

Esculin Use and Manufacturing

Uses

esculin 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. esculoside is utilized in formulations for the treatment of cellulite. es culoside is apparently beneficial for impaired microcirculation.

Manufacturing Info：

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

Use Classification：

Cosmetics -> Tonic

Computed Properties

Molecular Weight:340.28
XLogP3:-0.6
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:3
Exact Mass:340.07943208
Monoisotopic Mass:340.07943208
Topological Polar Surface Area:146
Heavy Atom Count:24
Complexity:495
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Esculin

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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Esculin

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