7,8-Dihydroxycoumarin supplier

Name
7,8-Dihydroxycoumarin
EINECS 207-632-8
CAS No. 486-35-1
Article Data40
CAS DataBase
Density 1.563 g/cm³
Solubility
Melting Point 265-268 °C (dec.)
Formula C₉H₆O₄
Boiling Point 430.4 °C at 760 mmHg
Molecular Weight 178.144
Flash Point 184.5 °C
Transport Information
Appearance solid
Safety 22-24/25-36-26
Risk Codes 25-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Daphnetin;2H-1-Benzopyran-2-one, 7,8-dihydroxy- (9CI);7,8-dihydroxy-coumarin;Daphnetol;5-18-03-00211 (Beilstein Handbook Reference);7,8-Dihydroxy-2H-1-benzopyran-2-one;2H-1-Benzopyran-2-one,7,8-dihydroxy-;7,8-dihydroxychromen-2-one;
PSA 70.67000
LogP 1.20420

Synthetic route

: 471-25-0
Propiolic acid

: 87-66-1
2-hydroxyresorcinol

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With ytterbium(III) trifluoromethanesulfonate hydrate at 80℃; for 0.0333333h; Reagent/catalyst; Microwave irradiation;	98%
With sulfuric acid at 120℃; for 1h;	70%
With sulfuric acid at 120℃; for 0.5h;	59%
With sulfuric acid at 124 - 126℃; for 0.833333h;	53.4%
With sulfuric acid at 125℃; for 0.833333h;

: 104819-86-5
7,8-dibenzyloxycoumarin

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With aluminum tri-bromide In nitrobenzene for 0.0833333h;	80%

: 617-48-1
malic acid

: 87-66-1
2-hydroxyresorcinol

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With sulfuric acid	65%
With sulfuric acid at 120 - 130℃; for 1h;	61%
Stage #1: malic acid With sulfuric acid at 20℃; for 0.166667h; Stage #2: 2-hydroxyresorcinol at 20 - 120℃; for 2h;	40%

: 2144-08-3
2,3,4-trihydroxybenzylaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 486-35-1
daphnetin

Conditions

Conditions	Yield
for 0.25h; Inert atmosphere; Reflux;	65%
for 4h; Reflux; Inert atmosphere;	65%

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

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With 2-iodoxybenzoic acid In dimethyl sulfoxide at 25℃; for 2h; Time; regioselective reaction;	59%

: 110-16-7
maleic acid

: 87-66-1
2-hydroxyresorcinol

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With sulfuric acid	20%

: 2067-86-9
8-formyl-7-hydroxycoumarin

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With pyridine; sodium hydroxide; dihydrogen peroxide

: 19484-74-3
7,8-Dihydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With sodium hydrogensulfite anschliessend mit Schwefelsaeure erhitzen;

: 2445-80-9
7,8-dimethoxy-chromen-2-one

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With hydrogen iodide In acetic acid for 2h; Heating;	20 mg

: 486-55-5
daphnin

A: 2280-44-6
D-Glucose

B: 486-35-1
daphnetin

Conditions

Conditions	Yield
With hydrogenchloride

: 20853-56-9, 22059-09-2
7-hydroxy-2-oxo-2H-chromen-8-yl β-D-glucopyranoside

A: 2280-44-6
D-Glucose

B: 486-35-1
daphnetin

Conditions

Conditions	Yield
With hydrogenchloride

: 110-86-1
pyridine

: 2067-86-9
8-formyl-7-hydroxycoumarin

: 623-11-0
1-methyl-4-nitrosobenzene

: 7722-84-1
dihydrogen peroxide

: 486-35-1
daphnetin

...Expand

daphnine: daphnine

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With mineral acid
With emulsin

: 108-24-7
acetic anhydride

pyrogallolaldehyde: pyrogallolaldehyde

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With sodium acetate at 170 - 180℃; Erwaermen des erhaltenen Daphnetin-diacetats mit Schwefelsaeure;
With sodium acetate

: 92439-17-3
2-<3,4-Dihydroxy-phenyl>-chromen-7-on, Anhydro-7,3',4'-trihydroxy-flaven-(4 oder 2)-ol

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

B: 486-35-1
daphnetin

Conditions

Conditions	Yield
With 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl In methanol; phosphate buffer at 25℃; for 0.0138889h; pH=7.4; Kinetics; Further Variations:; Reagents; reaction time; Oxidation;

: 7-O-(6'-acetoxy-β-D-glucopyranosyl)-8-hydroxycoumarin

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;

: 7-O-[6'-O-(3'',4''-dihydroxycinnamoyl)-β-D-glucopyranosyl]-8-hydroxycoumarin

A: 331-39-5
caffeic acid

B: 486-35-1
daphnetin

Conditions

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;

: 7-hydroxyl-8-O-[α-D-glucopyranosyl]-2H-benzopyran-2-one

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With hydrogenchloride; water for 3h; Heating;

: 19492-03-6
8-hydroxy-7-methoxy-2H-chromen-2-one

: 486-35-1
daphnetin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 20 mg / HI / acetic acid / 2 h / Heating View Scheme

: 76474-93-6
7-methoxy-8-[(3-methyl-2-butenyl)oxy]-2H-1-benzopyran-2-one

: 486-35-1
daphnetin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 15 mg / 10percent aq.H2SO4 / 1 h / Heating 3: 20 mg / HI / acetic acid / 2 h / Heating View Scheme

: 486-55-5
daphnin

: 486-35-1
daphnetin

Conditions

Conditions	Yield
Acid hydrolysis;

: 20853-56-9, 22059-09-2
7-hydroxy-2-oxo-2H-chromen-8-yl β-D-glucopyranoside

: 486-35-1
daphnetin

Conditions

Conditions	Yield
Acid hydrolysis;

: 31564-25-7
7-O-β-D-glucopyranosyl-8-methoxybenzopyranone

: 486-35-1
daphnetin

Conditions

Conditions	Yield
With water Acidic conditions;

: 186581-53-3, 908094-01-9
diazomethane

: 486-35-1
daphnetin

: 2445-80-9
7,8-dimethoxy-chromen-2-one

Conditions

Conditions	Yield
In methanol; diethyl ether at 20℃; for 2h;	100%

: 2082-59-9
pentanoic anhydride

: 486-35-1
daphnetin

: 2-oxo-2H-chromene-7,8-diyl dipentanoate

Conditions

Conditions	Yield
With pyridine; dmap at 20℃;	99%
With pyridine; dmap at 20℃;	99%

: 589-15-1
1-bromomethyl-4-bromobenzene

: 486-35-1
daphnetin

: C23H16Br2O4

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; Reflux;	99%

: 108-24-7
acetic anhydride

: 486-35-1
daphnetin

: 21784-71-4
2-oxo-2H-chromene-7,8-diyl diacetate

Conditions

Conditions	Yield
With dmap In pyridine at 20℃;	96.7%
With pyridine In dichloromethane	92%
With pyridine; dmap at 20℃;	51%

: 100-44-7
benzyl chloride

: 486-35-1
daphnetin

: 104819-86-5
7,8-dibenzyloxycoumarin

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 13h;	92%

: 2051-90-3
Dichlorodiphenylmethane

: 486-35-1
daphnetin

: 159979-62-1
2,2-Diphenyl-[1,3]dioxolo[4,5-h]chromen-8-one

Conditions

Conditions	Yield
at 160℃; for 0.166667h;	88.2%

: 123-62-6
propionic acid anhydride

: 486-35-1
daphnetin

: 2-oxo-2H-chromene-7,8-diyl di-propionate

Conditions

Conditions	Yield
With pyridine; dmap at 20℃;	84%
With pyridine; dmap at 20℃;	84%

: 2051-49-2
n-hexanoic anhydride

: 486-35-1
daphnetin

: 2-oxo-2H-chromene-7,8-diyl dihexanoate

Conditions

Conditions	Yield
With pyridine; dmap at 20℃;	78%

: 90446-67-6
4-((tert-butyldimethylsilyl)oxy)benzoyl chloride

: 486-35-1
daphnetin

: C35H42O8Si2

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 30℃; for 18h;	78%

: 7321-27-9
2-bromoanthracene

: 486-35-1
daphnetin

: C23H14O4

Conditions

Conditions	Yield
With cesium bicarbonate In toluene at 40℃; for 30h; Inert atmosphere; Irradiation;	77%

: 21615-34-9
2-Methoxybenzoyl chloride

: 486-35-1
daphnetin

: C25H18O8

Conditions

Conditions	Yield
With dmap In acetonitrile at 0 - 30℃; for 18h;	77%

: 1711-05-3
m-anisoyl chloride

: 486-35-1
daphnetin

: C25H18O8

Conditions

Conditions	Yield
With dmap In acetonitrile at 0 - 30℃; for 18h;	75%

: 100-07-2
4-methoxy-benzoyl chloride

: 486-35-1
daphnetin

: C25H18O8

Conditions

Conditions	Yield
With dmap In acetonitrile at 0 - 30℃; for 18h;	74%

: 340127-55-1
3,5-bis(tert-butyldimethylsilyl)oxybenzoyl chloride

: 486-35-1
daphnetin

: C47H70O10Si4

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 30℃; for 18h;	73%

: 870-63-3
prenyl bromide

: 486-35-1
daphnetin

: 81263-59-4
8-Hydroxy-7-isopentenyloxycoumarin

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetone	65%
With sodium hydrogencarbonate 1.) Me2CO, RT, 1 h, 2.) reflux, 24 h; Yield given. Multistep reaction;

: 6138-90-5
trans-geranyl bromide

: 486-35-1
daphnetin

: 562818-09-1
7-geranyloxy-8-hydroxycoumarin

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20℃; for 3h;	65%

: 552-45-4
1-chloromethyl-2-methylbenzene

: 486-35-1
daphnetin

: C25H22O4

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; Reflux;	63%

: 1461-04-7
(2E)-3,7-dimethyl-2-octen-1-ol

: 486-35-1
daphnetin

A: 8-[(3,7-dimethyl-2-octenyl)oxy]-7-hydroxy-2H-1-benzopyran-2-one

B: 7-[(3,7-dimethyl-2-octenyl)oxy]-8-hydroxy-2H-1-benzopyran-2-one

C: 7,8-Bis-((E)-3,7-dimethyl-oct-2-enyloxy)-chromen-2-one

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 10 - 20℃; Mitsunobu reaction; sonication;	A 30% B 61% C 4%

...Expand

: 16807-13-9
3-iodocarbazole

: 486-35-1
daphnetin

: C21H13NO4

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In toluene at 50℃; for 36h; Inert atmosphere; Irradiation;	60%

: 106-31-0
butanoic acid anhydride

: 486-35-1
daphnetin

: 2-oxo-2H-chromene-7,8-diyl dibutyrate

Conditions

Conditions	Yield
With pyridine; dmap at 20℃;	58%
With pyridine; dmap at 20℃;	58%

: 104-81-4
4-Methylbenzyl bromide

: 486-35-1
daphnetin

: 7,8-bis((4-methylbenzyl)oxy)-2H-chromen-2-one

Conditions

Conditions	Yield
Stage #1: daphnetin With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: 4-Methylbenzyl bromide In acetone at 65℃;	58%

: 620-19-9
1-chloromethyl-3-methyl-benzene

: 486-35-1
daphnetin

: 7,8-bis((4-methylbenzyl)oxy)-2H-chromen-2-one

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; Reflux;	58%

: 67-56-1
methanol

: 106-28-5
Farnesol

: 486-35-1
daphnetin

A: 19492-03-6
8-hydroxy-7-methoxy-2H-chromen-2-one

B: 2445-80-9
7,8-dimethoxy-chromen-2-one

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 10 - 20℃; Mitsunobu reaction; sonication;	A 52% B 10%

...Expand

: 106-93-4
ethylene dibromide

: 486-35-1
daphnetin

: 53324-43-9
7,8-(2',3'-dihydro-1',4'-dioxino)coumarin

Conditions

Conditions	Yield
With potassium hydroxide In water Heating;	47%

: 458-35-5, 32811-40-8, 69056-21-9
coniferal alcohol

: 486-35-1
daphnetin

: (2R,3R)-2-(4-Hydroxy-3-methoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-1,4,5-trioxa-phenanthren-6-one

Conditions

Conditions	Yield
With Na,K-phosphate buffer; horseradish peroxidase at 37℃; for 168h;	43.1%

7,8-Dihydroxycoumarin Specification

The IUPAC name of 7,8-Dihydroxycoumarin is 7,8-dihydroxychromen-2-one. With the CAS registry number 486-35-1, it is also named as Daphnetin. The product's categories are Pharmaceutical Raw Materials; Coumarins. It is solid which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.77; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.76; (4)ACD/LogD (pH 7.4): 0.45; (5)ACD/BCF (pH 5.5): 2.22; (6)ACD/BCF (pH 7.4): 1.09; (7)ACD/KOC (pH 5.5): 61.44; (8)ACD/KOC (pH 7.4): 30.11; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 44.76 Å²; (13)Index of Refraction: 1.689; (14)Molar Refractivity: 43.52 cm³; (15)Molar Volume: 113.9 cm³; (16)Polarizability: 17.25×10^-24cm³; (17)Surface Tension: 75.6 dyne/cm; (18)Enthalpy of Vaporization: 71.23 kJ/mol; (19)Vapour Pressure: 5.18E-08 mmHg at 25°C.

Preparation of 7,8-Dihydroxycoumarin: this chemical can be obtained by 7,8-dibenzyloxycoumarin. This reaction will need reagent AlBr₃ and solvent nitrobenzene. The reaction time is 5 min. The yield is about 80%.

Uses of 7,8-Dihydroxycoumarin: it is used to produce 7,8-dibenzyloxycoumarin. This reaction will need reagent K₂CO₃ and solvent nitrobenzene at the temperature of 60°C. The reaction time is 13 hour (s) and the yield is about 92%.

When you are using this chemical, please be cautious about it as the following:
It is not only toxic if swallowed, but also irritating to eyes, respiratory system and skin. So people shouold not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C/2Oc1c(O)c(O)ccc1\C=C\2
2. InChI: InChI=1/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H
3. InChIKey: ATEFPOUAMCWAQS-UHFFFAOYAC

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	429mg/kg (429mg/kg)	Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 22, Pg. 87, 1987.
mouse	LD50	intravenous	375mg/kg (375mg/kg)	Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 22, Pg. 87, 1987.
mouse	LD50	oral	5370mg/kg (5370mg/kg)	Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 22, Pg. 87, 1987.

Product Name

7,8-Dihydroxycoumarin

Synthetic route

7,8-Dihydroxycoumarin Specification

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