Esculetin supplier | CasNO.305-01-1

Name
Esculetin
EINECS 206-161-5
CAS No. 305-01-1
Article Data50
CAS DataBase
Density 1.563 g/cm³
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
Appearance yellowish crystalline powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Coumarin,6,7-dihydroxy- (8CI);6,7-Dihydroxy-2-benzopyrone;6,7-Dihydroxycoumarin;Aesculetin;Asculetine;Cichorigenin;Cichoriin aglycon;Esculin aglycon;NSC 26428;
PSA 70.67000
LogP 1.20420

Synthetic route

: 895-61-4
6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one

: 305-01-1
aesculetin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With aluminium(III) iodide In acetonitrile at 80℃; for 18h;	77%

: 331-39-5
cis-caffeic acid

: 305-01-1
aesculetin

Conditions

Conditions	Yield
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

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;

: 531-75-9
esculin

A: 492-62-6
alpha-D-glucopyranose

B: 305-01-1
aesculetin

Conditions

Conditions	Yield
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

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

...Expand

: 531-75-9
esculin

: 305-01-1
aesculetin

Conditions

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;

aesculin: aesculin

: 305-01-1
aesculetin

Conditions

Conditions	Yield
With diluted acid
With emulsin
With hydrogenchloride Behandeln mit Wasser, in Alkohol und mit Bleiacetat; anschliessend Behandeln mit Alkohol, Wasser und Schwefelwasserstoff;
durch Spaltung mit Aesculase;

cichoriin: cichoriin

: 305-01-1
aesculetin

Conditions

Conditions	Yield
With sulfuric acid

esculetin-carboxylic acid-(3): esculetin-carboxylic acid-(3)

: 305-01-1
aesculetin

Conditions

Conditions	Yield
trockne Destillation;

: 108-24-7
acetic anhydride

oxyhydroquinonaldehyde: oxyhydroquinonaldehyde

: 305-01-1
aesculetin

Conditions

Conditions	Yield
With sodium acetate at 170 - 180℃; Verseifen der erhaltenen Diacetylverbindung;

: 93-35-6
7-hydroxy-2H-chromen-2-one

sodium peroxo disulfate: sodium peroxo disulfate

aqueous NaOH-solution: aqueous NaOH-solution

: 305-01-1
aesculetin

...Expand

: 92-61-5
7-hydroxy-6-methoxy-2H-1-benzopyran-2-one

: 10034-85-2
hydrogen iodide

A: 305-01-1
aesculetin

B: 74-88-4
methyl iodide

...Expand

: 7647-01-0
hydrogenchloride

: 6,7-dihydroxy-2-oxo-chroman-3-sulfonic acid

A: 305-01-1
aesculetin

B sulfur dioxide: sulfur dioxide

...Expand

: 7664-93-9
sulfuric acid

: 6,7-dihydroxy-2-oxo-chroman-3-sulfonic acid

A: 305-01-1
aesculetin

B sulfur dioxide: sulfur dioxide

...Expand

: 531-75-9
esculin

A: 305-01-1
aesculetin

B sodium disulfite: sodium disulfite

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) K2CO3, 2) 5percent H2SO4 / acetone 2: AlCl3 View Scheme

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.

Product Name

Esculetin

Synthetic route

Esculetin Specification

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