Esculin

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

Molecular Weight：340.28214

Modify Date.: 2022-11-05 08:20

Introduction: Aesculin (also Esculin) is a glucoside compound, which occurs naturally in unprocessed seeds, leaves, bark, and flowers of horse chestnut. Aesculin is used for the identification of bacteria, for the treatment of hemorrhoids and venous peripheral diseases. In cosmetics, aesculin was found to be effective in the treatment of aging skin. Owing to its ultraviolet absorbing activity, aesculin is employed in tanning preparations. Aesculin can be also used as a substrate for the detection of ß-gluocosidase activity in polyacrylamide gels. View more+

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1. Names and Identifiers

1.1 Name: Esculin
1.2 Synonyms: (-)-Esculin 2H-1-Benzopyran-2-one, 6-(beta-D-glucopyranosyloxy)-7-hydroxy- 2H-1-Benzopyran-2-one, 6-(β-D-glucopyranosyloxy)-7-hydroxy- 6-(β-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one 6-(β-D-Glucopyranosyloxy)-7-hydroxycoumarin 6,7-Dihydroxycoumarin 6-glucoside 6,7-DIHYDROXYCOUMARIN-6-O-GLUCOSIDE Aesculin BICOLOIN Crataegin Enallachrome Escosyl Esculetin 6-O-glucoside Esculetin 6-β-D-glucoside ESCULETIN-6-GLUCOSIDE ESCULETIN-6-O-GLUCOSIDE ESCULIN Esculine Esculinsesquimonohydrate ESCULOSIDE Polychrom Polychrome Vitamin C2

1.3 CAS No.: 531-75-9

1.4 CID: 5281417

1.5 EINECS(EC#): 208-517-5

1.6 Molecular Formula: C15H16O9 (isomer)

1.7 Inchi: InChI=1S/C15H16O9/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/t10-,12-,13+,14-,15-/m1/s1

1.8 InChIkey: XHCADAYNFIFUHF-TVKJYDDYSA-N

1.9 Canonical Smiles: C1=CC(=O)OC2=CC(=C(C=C21)OC3C(C(C(C(O3)CO)O)O)O)O

1.10 Isomers Smiles: C1=CC(=O)OC2=CC(=C(C=C21)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O

2. Properties

2.1 Density: 1.679

2.1 Melting point: 203-205℃

2.1 Boiling point: 697.7 oC at 760 mmHg

2.1 Refractive index: -79 ° (C=2.4, 50% Dioxane)

2.1 Flash Point: 262.8 oC

2.1 Precise Quality: 340.07900

2.1 PSA: 149.82000

2.1 logP: -1.32270

2.1 Solubility: methanol: 50?mg/mL hot, clear to very faintly turbid, yellow-green fluoresc.

2.2 Appearance: cream powder.

2.3 Chemical Properties: White to nearly white

2.4 Color/Form: Clear

2.5 pKa: 7.00±0.20(Predicted)

2.6 Water Solubility: MODERATELY SOLUBLE

2.7 Stability: Stable. Incompatible with strong oxidizing agents.

2.8 StorageTemp: Store at RT.

3. Use and Manufacturing

3.1 Definition: ChEBI: A hydroxycoumarin that is the 6-O-beta-D-glucoside of esculetin. EsculinSupplier

3.2 Usage: 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.

4. Safety and Handling

4.1 Hazard Codes: F; C; Xi

4.1 Risk Statements: R11

4.1 Safety Statements: S24/25

4.1 RIDADR: UN 2924 3/PG 2

4.1 WGK Germany: 3

4.1 RTECS: DJ3085000

4.1 Safety: Hazard Codes:?F,C,Xi
Risk Statements: 11-20/21/22-34-68/20/21/22-36/37/38?
R11:Highly flammable.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R34:Causes burns.?
R68:Possible risk of irreversible effects.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39-45-24/25-36/37?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S24/25:Avoid contact with skin and eyes.?
S36/37:Wear suitable protective clothing and gloves.
RIDADR: UN 2924 3/PG 2
WGK Germany: 3
RTECS: DJ3085000
F: 3-10-23

4.2 Specification: ?2H-1-Benzopyran-2-one,6-(b-D-glucopyranosyloxy)-7-hydroxy- , with CAS number of 531-75-9, can be called?2H-1-Benzopyran-2-one, 6-(beta-D-glucopyranosyloxy)-7-hydroxy- ; 6-(beta-d-glucopyranosyloxy)-7-hydroxy-2h-1-benzopyran-2-on ; Bicolorin;Crataegin ; Enallachrome ; Escosyl ; Esculetin 6-beta-D-glucoside ; Esculine .

4.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1900mg/kg (1900mg/kg)	?	Acta Pharmaceutica Vol. 48, Pg. 127, 1998.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

1H NMR : 400 MHz in DMSO-d6

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Other Information

7.0 Merck: 3698

7.1 Description: Aesculin (also Esculin) is a glucoside compound, which occurs naturally in unprocessed seeds, leaves, bark, and flowers of horse chestnut. Aesculin is used for the identification of bacteria, for the treatment of hemorrhoids and venous peripheral diseases. In cosmetics, aesculin was found to be effective in the treatment of aging skin. Owing to its ultraviolet absorbing activity, aesculin is employed in tanning preparations. Aesculin can be also used as a substrate for the detection of ß-gluocosidase activity in polyacrylamide gels.

7.2 References: [1] Anna D. Orla-Jensen, About the application of aesculin for the identification of bacteria, APMIS, 1934, vol. 11, 312-322
[2] S. Srijayanta, A. Raman and B. L. Goodwin, A comparative study of the constituents of Aesculus hippocastanum and Aesculus indica, Journal of Medical Food, 1999, vol. 2, 45-50
[3] Ki-Sun Kwon, Jaehoon Lee, Hyung Gyoo Kang and Yung Chil Hah, Detection of ß-Glucosidase Activity in Polyacrylamide Gels with Esculin as Substrate, Appl. Environ. Microbil., 1994, vol. 80, 4584-4586
[4] Dennis J Mckenna, Kenneth Jones, Kerry Hughes and Virginia M Tyler, Botanical Medicines: The Desk Reference for Major Herbal Supplements, Second Edition, 2011

7.3 Chemical Properties: White to nearly white

7.4 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.

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

7.6 Definition: ChEBI: A hydroxycoumarin that is the 6-O-beta-D-glucoside of esculetin.

8. Computational chemical data

Molecular Weight: 340.28214g/mol
Molecular Formula: C₁₅H₁₆O₉
Compound Is Canonicalized: True
XLogP3-AA: -0.6
Exact Mass: 340.07943208
Monoisotopic Mass: 340.07943208
Complexity: 495
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 9
Topological Polar Surface Area: 146
Heavy Atom Count: 24
Defined Atom Stereocenter Count: 5
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwPAAAAAAAAAAAAAAAAAAAAAAAAAA0QIAAAAAAAACBAAAAGgAACAAADBSwmAMwDoAABgCIAiDSCAACCAAgIAAIiAAGiMgdNyKGMRqieiOlwBUPuYfA4DwOIQABCAAIQABCAAIQABCAAAAAAAAAAA==

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Purity:99%Packing: 200kg/bag FOB
Price: 1 USD/kilogram
Time: 2023/06/09

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Esculin CAS 531-75-9