531-75-9

Basic information

• Product Name: Esculin
• Synonyms: 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
• CAS NO: 531-75-9
• Molecular Formula: C₁₅H₁₆O₉
• Molecular Weight: 340.28
• EINECS: 208-517-5
• Product Categories: Biochemistry;Glucose;Glycosides;Sugars;Functional Products;Natural Plant Extract;Pyrrolidonyl peptidase;Enzyme Substrates;Substrates by Enzyme;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 531-75-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 203 °C
• Boiling Point: 396.1°C (rough estimate)
• Flash Point: 15 °C
• Appearance: Clear/Liquid
• Density: 0.791 g/mL at 20 °C
• Vapor Pressure: 1.97E-20mmHg at 25°C
• Refractive Index: -79 ° (C=2.4, 50% Dioxane)
• Storage Temp.: Store at RT.
• Solubility: methanol: 50 mg/mL hot, clear to very faintly turbid, yello
• PKA: 7.00±0.20(Predicted)
• Water Solubility: MODERATELY SOLUBLE
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 3698
• CAS DataBase Reference: Esculin(CAS DataBase Reference)
• NIST Chemistry Reference: Esculin(531-75-9)
• EPA Substance Registry System: Esculin(531-75-9)

Safety Data

• Hazard Codes: F,C,Xi
• Statements: 11-20/21/22-34-68/20/21/22-36/37/38
• Safety Statements: 26-36/37/39-45-24/25-36/37-16
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• RTECS: DJ3085000
• F: 3-10-23
• Hazardous Substances Data: 531-75-9(Hazardous Substances Data)

Usage

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 ?-gluocosidase activity in polyacrylamide gels.

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 ?-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

Chemical Properties

White to nearly white

Uses

Different sources of media describe the Uses of 531-75-9 differently. You can refer to the following data:
1. 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.
2. esculoside is utilized in formulations for the treatment of cellulite. es culoside is apparently beneficial for impaired microcirculation.
3. Esculin hydrate has been used as a component of sporulation-inducing esculin agar. It has also been used for esculin uptake assay.

Definition

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

General Description

Esculin hydrate has vasoprotective and venotonic properties.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Esculin is a coumarin glycoside that demonstrates antioxidant activitites and protection against chemically-induced carcinogenesis. Esculin is utilized in microbiology for the isolation and identification of Enterococcus (group D streptococci).

InChI:InChI=1/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+/m0/s1

Synthetic route

7-benzyloxy-6-β-D-glucopyranosyloxy-coumarin (34340-36-8) → esculin (531-75-9)

Conditions	Yield
With methanol; Pd-BaSO4 Hydrogenation;

6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one (895-61-4) → esculin (531-75-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous alkaline solution; acetone 2: ammonia; methanol 3: palladium/barium sulfate; methanol / Hydrogenation View Scheme
Multi-step reaction with 3 steps 1: aqueous alkaline solution; acetone 2: diluted methanol. NaOH-solution 3: palladium/barium sulfate; methanol / Hydrogenation View Scheme

benzyl chloride (100-44-7) → esculin (531-75-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol; potassium carbonate 2: aqueous alkaline solution; acetone 3: ammonia; methanol 4: palladium/barium sulfate; methanol / Hydrogenation View Scheme
Multi-step reaction with 4 steps 1: potassium hydrogencarbonate 2: aqueous alkaline solution; acetone 3: diluted methanol. NaOH-solution 4: palladium/barium sulfate; methanol / Hydrogenation View Scheme

7-benzyloxy-6-(tetra-O-acetyl-β-D-glucopyranosyloxy)-coumarin (34340-35-7) → esculin (531-75-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia; methanol 2: palladium/barium sulfate; methanol / Hydrogenation View Scheme
Multi-step reaction with 2 steps 1: diluted methanol. NaOH-solution 2: palladium/barium sulfate; methanol / Hydrogenation View Scheme

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → esculin (531-75-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous alkaline solution; acetone 2: ammonia; methanol 3: palladium/barium sulfate; methanol / Hydrogenation View Scheme
Multi-step reaction with 3 steps 1: aqueous alkaline solution; acetone 2: diluted methanol. NaOH-solution 3: palladium/barium sulfate; methanol / Hydrogenation View Scheme

C88H56N4(4+)*4Cl(1-)*2C15H16O9 → C88H60N4O4 + esculin (531-75-9)

Conditions	Yield
With water; sodium hydrogencarbonate at 20℃;

C88H56N4(4+)*4Cl(1-)*2C15H16O9 → C88H56N4(4+)*4Cl(1-) + esculin (531-75-9)

Conditions	Yield
With sodium hydrogencarbonate In water-d2 at 20℃; for 18h;

C88H56N4(4+)*4Cl(1-) + esculin (531-75-9) → C88H56N4(4+)*4Cl(1-)*2C15H16O9

Conditions	Yield
In water-d2 at 20℃; for 0.0833333h; Time;	100%

dimethyl sulfate (77-78-1) + esculin (531-75-9) → 7-methoxycoumarin-6-β-D-glucopyranoside (20186-29-2)

Conditions	Yield
Stage #1: esculin With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide	100%

2,2-dimethoxy-propane (77-76-9) + esculin (531-75-9) → 6-O-esculetinyl 4',6'-di-O-isopropylidene-β-D-glucopyranoside (69711-94-0)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃; for 24h;	98%

ethyl bromide (74-96-4) + esculin (531-75-9) → C17H20O9

Conditions	Yield
Stage #1: esculin With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: ethyl bromide In N,N-dimethyl-formamide	90%

4-thiaheptane-1,7-dioic acid (111-17-1) + esculin (531-75-9) → aesculin thiodipropionic acid ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 40℃; for 4h; Temperature; Reagent/catalyst; Solvent; Sonication; Inert atmosphere;	89.03%
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 40℃; for 4h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;	89.03%

Thioctic acid (1077-28-7, 62-46-4) + esculin (531-75-9) → C23H28O10S2

Conditions	Yield
With thionyl chloride; dicyclohexyl-carbodiimide In acetonitrile at 35℃; for 4h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere; Sonication;	88.79%

(R)-1,2-dithiolane-3-pentanoic acid (1200-22-2) + esculin (531-75-9) → aesculin lipoic acid ester

Conditions	Yield
With thionyl chloride; dicyclohexyl-carbodiimide In acetonitrile at 35℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere; Sonication;	88.79%

benzyl chloride (100-44-7) + esculin (531-75-9) → 7-benzyloxy-6-D-glucopyranosyloxycoumarin

Conditions	Yield
With potassium iodide; potassium carbonate In N-methyl-acetamide	86.4%

para-bromoacetophenone (99-90-1) + esculin (531-75-9) → C23H22O10

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Heck Reaction; Irradiation; Inert atmosphere; stereoselective reaction;	80%

3-acetyl-5-bromopyridine (38940-62-4) + esculin (531-75-9) → C22H21NO10

Conditions	Yield
With potassium dihydrogenphosphate at 25℃; for 16h; Inert atmosphere; Irradiation;	80%

allyl bromide (106-95-6) + esculin (531-75-9) → 6-[1-(β-D-(glucopyranosyloxy))]-7-(3-alyloxy)-2H-1-benzopyran-2-one (241155-08-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 9h; Alkylation;	62%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 7h;

esculin (531-75-9) → esculin 7,3',4',5',6'-O-pentasulfate

Conditions	Yield
With triethylamine sulfur trioxide In N,N-dimethyl acetamide at 65℃; for 23h;	60%
Stage #1: esculin With triethylamine sulfur trioxide In N,N-dimethyl acetamide at 65℃; for 24h; Stage #2: With triethylamine In N,N-dimethyl acetamide; acetone at 4℃; for 24h; Stage #3: With sodium acetate In water	26%

para-chloroacetophenone (99-91-2) + esculin (531-75-9) → C23H22O10

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 20℃; for 36h; Heck Reaction; Irradiation; Inert atmosphere; stereoselective reaction;	46%

N,N-Dimethylcarbamoyl chloride (79-44-7) + esculin (531-75-9) → C18H21NO10 + C21H26N2O11

Conditions	Yield
Stage #1: esculin With pyridine; tetra(n-butyl)ammonium hydroxide; sodium hydroxide at 20℃; for 0.166667h; Stage #2: N,N-Dimethylcarbamoyl chloride	A 37% B 1.3%

cinnamoyl chloride (102-92-1) + esculin (531-75-9) → C24H22O10

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 0.333333h;	27%

4-chloro-benzoyl chloride (122-01-0) + esculin (531-75-9) → C22H19ClO10

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 0.333333h;	24%

4-fluorobenzoyl chloride (403-43-0) + esculin (531-75-9) → C22H19FO10

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 0.333333h;	16%

4-hydroxyphenylacryloyl chloride (52820-26-5) + esculin (531-75-9) → C24H22O11

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 0.333333h;	7.7%

4-hydroxy-3-methoxyphenylacryloyl chloride (138769-50-3) + esculin (531-75-9) → C25H24O12

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 0.333333h;	6.5%

diazomethane (186581-53-3, 908094-01-9) + esculin (531-75-9) → 7-methoxycoumarin-6-β-D-glucopyranoside (20186-29-2)

Conditions	Yield
With methanol; diethyl ether
With diethyl ether; ethanol

esculin (531-75-9) + methyl iodide (74-88-4) → 7-methoxycoumarin-6-β-D-glucopyranoside (20186-29-2)

Conditions	Yield
With potassium hydroxide
With potassium carbonate; acetone
With methanol; potassium carbonate

dimethyl sulfate (77-78-1) + esculin (531-75-9) → isoscopoletin (776-86-3)

Conditions	Yield
With sulfuric acid; potassium carbonate In acetone
With rhamnodiastase; potassium carbonate 1) acetone; 2) enzymatic hydrolysis;; Multistep reaction;

esculin (531-75-9) → D-Glucose (2280-44-6)

Conditions	Yield
With β-D-glucosidase of Sclerotium rolfsii In water at 65℃; for 0.5h; enzymic hydrolysis, rate;

esculin (531-75-9) → D-Glucose (2280-44-6) + aesculetin (305-01-1)

Conditions	Yield
With sulfuric acid
With citrate buffer; phosphate buffer; soybean β-glucosidase at 40℃; pH=5.0; Enzyme kinetics;
With β-cyclodextrin dicyanohydrin; Fe(III) ammonium citrate In phosphate buffer at 25 - 60℃; pH=8.0; Kinetics;

esculin (531-75-9) → alpha-D-glucopyranose (492-62-6) + aesculetin (305-01-1)

Conditions	Yield
With sulfuric acid hydrolysis;

esculin (531-75-9) → aesculetin (305-01-1)

Conditions	Yield
With acetate buffer; β-glucosidase at 37℃;
With MES buffer; β-glucosidase at 37℃; for 0.5h; pH=7.0;
With naringinase from Aspergillus aculeatus JMUdb058 In aq. buffer at 50 - 100℃; for 0.583333h; pH=4; Kinetics; Enzymatic reaction;
With water; acetic acid In ethanol at 150℃; under 15201 Torr; for 1h; pH=2.6; Reagent/catalyst; Microwave irradiation; Sealed tube;

benzyl bromide (100-39-0) + esculin (531-75-9) → 7-benzyloxy-6-β-D-glucopyranosyloxy-coumarin (34340-36-8)

Conditions	Yield
With potassium carbonate In ethanol Heating;

esculin (531-75-9) → 7-allyloxy-6-benzyloxy-chromen-2-one (66300-99-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / K2CO3 / dimethylformamide / 9 h / 90 °C 2: 79 percent / H2SO4 / H2O 3: 63 percent / K2CO3; NaI / dimethylformamide View Scheme

esculin (531-75-9) → 8-allyl-6-benzyloxy-7-hydroxy-chromen-2-one (66301-00-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / K2CO3 / dimethylformamide / 9 h / 90 °C 2: 79 percent / H2SO4 / H2O 3: 63 percent / K2CO3; NaI / dimethylformamide 4: 87 percent / 215 - 225 °C / 1 Torr View Scheme

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 34340-35-7 7-benzyloxy-6-(tetra-O-acetyl-β-D-glucopyranosyloxy)-coumarin 
• 100-44-7 benzyl chloride 
• 895-61-4 6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one 
• 34340-36-8 7-benzyloxy-6-β-D-glucopyranosyloxy-coumarin 

Downstream Products

• 250639-99-7 (6-benzyloxy-7-hydroxy-2-oxo-2H-chromen-8-yl)-acetaldehyde 
• 776-86-3 isoscopoletin 
• 50489-63-9 5-ethoxy-2,4-dimethoxy-cinnamic acid methyl ester 
• 305-01-1 aesculetin 
• 50-99-7 D-glucose 
• 66301-00-6 8-allyl-6-benzyloxy-7-hydroxy-chromen-2-one 
• 66300-99-0 7-allyloxy-6-benzyloxy-chromen-2-one 
• 492-62-6 alpha-D-glucopyranose 
• 2280-44-6 D-Glucose 

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