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Esculetin
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Name

Esculetin

 EINECS 206-161-5
CAS No. 305-01-1 Density 1.563 g/cm3
PSA 70.67000 LogP 1.20420
Solubility slightly soluble in water Melting Point 271-273 °C(lit.)
Formula C9H6O4 Boiling Point 469.7 °C at 760 mmHg
Molecular Weight 178.144 Flash Point 201.4 °C
Transport Information N/A Appearance yellowish crystalline powder
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 305-01-1 (Esculetin) Hazard Symbols IrritantXi
Synonyms

Coumarin,6,7-dihydroxy- (8CI);6,7-Dihydroxy-2-benzopyrone;6,7-Dihydroxycoumarin;Aesculetin;Asculetine;Cichorigenin;Cichoriin aglycon;Esculin aglycon;NSC 26428;

Article Data 50

Esculetin Synthetic route

895-61-4

6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one

305-01-1

aesculetin

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In methanol Product distribution / selectivity;100%
617-48-1

malic acid

613-03-6

1,2,4-triacetoxybenzene

305-01-1

aesculetin

Conditions
ConditionsYield
With sulfuric acid for 2h; Heating;85%
Stage #1: malic acid; 1,2,4-triacetoxybenzene With sulfuric acid at 100℃; for 2h;
Stage #2: With acetic acid at 120℃; for 18h;		78%
With sulfuric acid at 80℃; for 1.5h;65%
494-56-4

ayapin

305-01-1

aesculetin

Conditions
ConditionsYield
Stage #1: ayapin; aluminum tri-bromide In ethanethiol at 0 - 20℃;
Stage #2: With hydrogenchloride In water at 0 - 20℃; Product distribution / selectivity;		84.4%

esculetin acetonide

305-01-1

aesculetin

Conditions
ConditionsYield
With water; acetic acid Product distribution / selectivity;83.7%
With hydrogenchloride; water at 120℃; for 2h; Product distribution / selectivity;72%
35094-87-2

2,4,5-trihydroxybenzaldehyde

108-24-7

acetic anhydride

305-01-1

aesculetin

Conditions
ConditionsYield
With sodium acetate In N,N-dimethyl-formamide at 180℃; for 5h; Product distribution / selectivity;80%
120-08-1

Scoparone

305-01-1

aesculetin

Conditions
ConditionsYield
With aluminium(III) iodide In acetonitrile at 80℃; for 18h;77%
331-39-5

cis-caffeic acid

305-01-1

aesculetin

Conditions
ConditionsYield
With phenolase 1.) sodium phosphate buffer pH=6.6, room temp., 40 min; 2.) boiling, 3 min;40 mg
531-75-9

esculin

A

2280-44-6

D-Glucose

B

305-01-1

aesculetin

Conditions
ConditionsYield
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;
531-75-9

esculin

A

492-62-6

alpha-D-glucopyranose

B

305-01-1

aesculetin

Conditions
ConditionsYield
With sulfuric acid hydrolysis;
619-60-3

4-(N,N-dimethylamino)phenol

C9H5O4

A

305-01-1

aesculetin

B

54737-34-7

4-(N,N-dimethylamino)phenoxyl radical

Conditions
ConditionsYield
With potassium hydroxide In water Equilibrium constant; Irradiation;

Esculetin Specification

The Esculetin is an organic compound with the formula C9H6O4. The IUPAC name of this chemical is 6,7-dihydroxychromen-2-one. With the CAS registry number 305-01-1, it is also named as 2H-1-benzopyran-2-one, 6,7-dihydroxy-. The product's categories are Coumarins; Analytical Chemistry; Mass Spectrometry; Matrix Materials (MALDI-TOF-MS). Besides, it is a yellowish crystalline powder, which is the intermediate of anti-asthmatic drugs.

Physical properties about Esculetin are: (1)ACD/LogP: 0.98; (2)ACD/LogD (pH 5.5): 0.98; (3)ACD/LogD (pH 7.4): 0.8; (4)ACD/BCF (pH 5.5): 3.24; (5)ACD/BCF (pH 7.4): 2.18; (6)ACD/KOC (pH 5.5): 80.6; (7)ACD/KOC (pH 7.4): 54.11; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 44.76 Å2; (12)Index of Refraction: 1.689; (13)Molar Refractivity: 43.52 cm3; (14)Molar Volume: 113.9 cm3; (15)Polarizability: 17.25×10-24cm3; (16)Surface Tension: 75.6 dyne/cm; (17)Density: 1.563 g/cm3; (18)Flash Point: 201.4 °C; (19)Enthalpy of Vaporization: 76.01 kJ/mol; (20)Boiling Point: 469.7 °C at 760 mmHg; (21)Vapour Pressure: 1.91E-09 mmHg at 25°C.

Preparation: this chemical can be prepared by hydroxysuccinic acid. This reaction will need reagent H2SO4.



Uses of Esculetin: it can be used to produce [1,3]dioxolo[4,5-g]chromen-6-one bt heating. It will need reagent K2CO3 and solvent dimethylsulfoxide with reaction time of 3 hours. The yield is about 90%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C/2Oc1cc(O)c(O)cc1\C=C\2
(2)InChI: InChI=1/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
(3)InChIKey: ILEDWLMCKZNDJK-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
(5)Std. InChIKey: ILEDWLMCKZNDJK-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1500mg/kg (1500mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 714, 1968.

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