7,8-Dihydroxycoumarin

Iupac Name：7,8-dihydroxychromen-2-one

Molecular Weight：178.143

Modify Date.: 2022-11-29 12:19

Introduction:

Daphnetin (7,8-dihydroxycoumarin), one coumarin derivative isolated from plants of the Genus Daphne, is a protein kinase inhibitor, with IC50s of 7.67 μM, 9.33 μM and 25.01 μM for EGFR, PKA and PKC in vitro, respectively[1][2]. Daphnetin (7,8-dihydroxycoumarin) is a secondary metabolite of plants used in folk medicine to counter inflammatory and allergic diseases, also has been clinically used in the treatment of coagulation disorders, rheumatoid arthritis with anti-malarian and anti-pyr

7,8-dihydroxycoumarin is a hydroxycoumarin.

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1. Names and Identifiers

1.1 Name: 7,8-Dihydroxycoumarin
1.2 Synonyms: 2H-1-Benzopyran-2-one, 7,8-dihydroxy- 7,8-dihydroxy-2h-1-benzopyran-2-on 7,8-DIHYDROXY-2H-1-BENZOPYRAN-2-ONE 7,8-Dihydroxy-2H-chromen-2-one 7,8-DIHYDROXY-CHROMEN-2-ONE 7,8-Dihydroxychromen-2-one 7,8-dihydroxy-coumari 7,8-dihydroxy-coumarin 7,8-Diydroxycoumarin AKOS 213-37 DAPHNETIN EINECS 207-632-8 MFCD00016977 TCMDC-125839

1.3 CAS No.: 486-35-1

1.4 CID: 5280569

1.5 EINECS(EC#): 207-632-8

1.6 Molecular Formula: C9H6O4 (isomer)

1.7 Inchi: InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H

1.8 InChkey: ATEFPOUAMCWAQS-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=C(C2=C1C=CC(=O)O2)O)O

1.10 Isomers Smiles: C1=CC(=C(C2=C1C=CC(=O)O2)O)O

2. Properties

2.1 Density: 1.563

2.1 Melting point: 265-268°C (dec.)

2.1 Boiling point: 430.4 °C at 760 mmHg

2.1 Refractive index: 1.689

2.1 Flash Point: 430.4 °C at 760 mmHg

2.1 Precise Quality: 178.02700

2.1 PSA: 70.67000

2.1 logP: 1.20420

2.1 Appearance: solid

2.2 Color/Form: White cryst.

2.3 pKa: 7.61±0.20(Predicted)

2.4 StorageTemp: room temp

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 2 companies. For more detailed information, please visit ECHA C&L website

Of the 1 notification(s) provided by 1 of 2 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362

3.2 Purification Methods: Crystallise it from aqueous EtOH. It can be sublimed. [Beilstein 18/3 V 202.]. 7,8-DihydroxycoumarinSupplier

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R25

4.1 Safety Statements: S22;S24/25

4.1 Hazard Declaration: H315

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

4.1 WGK Germany: 2

4.1 RTECS: GN6382600

4.1 Specification

The 7,8-Dihydroxycoumarin with cas registry number of 486-35-1, belongs to the following product categorie: (1)Pharmaceutical Raw Materials; (2)Coumarins. It has the systematic name of 7,8-dihydroxy-2H-chromen-2-one.

Physical properties about this chemical are: (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: this chemical can be prepared 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 can be used to produce 7,8-dibenzyloxycoumarin. This reaction will need reagent K2CO3 and solvent nitrobenzene. The reaction time is 13 hour(s) with reaction temperature of 60 ℃.. The yield is about 92%.

When you are using this chemical, please be cautious about it as the following:
The 7,8-Dihydroxycoumarin is toxic if swallowed, so avoid contact with skin and eyes.
The 7,8-Dihydroxycoumarin irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If 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/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;
(4)Std. InChI: InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H;
(5)Std. InChIKey: ATEFPOUAMCWAQS-UHFFFAOYSA-N

The toxicity data is as follows:

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.

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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

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

486-35-1Total: 1 Synthesis Route

110-16-7 327 Suppliers

87-66-1 311 Suppliers

486-35-1 109 Suppliers

Literatures:
Reisch, Johannes; Wickramasinghe, Anura; Kumar, Vijaya Monatshefte fuer Chemie, 1988 , vol. 119, p. 1333 - 1339
Yield: ~20%

8. Precursor and Product

precursor:

110-16-7

87-66-1

product :

21784-71-4

76474-93-6

19492-03-6

477770-79-9

2445-80-9

9. Other Information

9.0 Merck: 14,2817

9.1 Description: Daphnetin, mainly extracted from Yu Ruixiang Changbai Daphne (Daphne Korean Nakai), Daphne giraldii Nitsche bark, and root bark, is the main efficacy component of the plants D.tangutica Maxim and D.retttsa Hemsl. Changbai daphnes has the pharmacological effects of warming the spleen and stomach, relaxing the muscles and joints, and promoting circulation. In TCM, it’s commonly used as medicines for treatment of injuries. Because Changbai daphne is a pungent and warm natured herbal medicine, it was used to warm the spleen and stomach by dispelling cold.

9.2 Physical properties: Appearance: white or off-white powder, odorless, and tasteless; Solubility: slightly soluble in methanol (equilibrium solubility of 485.4? μg/mL), slightly soluble in ethanol (equilibrium solubility of 230.06?μg/mL), and insoluble in water (equilibrium solubility of 176.7?μg/mL) ; Melting point: 262–264?°C.

9.3 History: Changbai daphne, a Chinese traditional medicine in clinic, is mainly used for treatment of coronary heart disease, rheumatoid arthritis, thromboangiitis obliterans, etc. Changbai daphne belongs to the first-class protective plants in Jilin province in China, and the rarity restricted the drug development. Scientists tried to find the effective components of Changbai daphne. In 1977, scientists of phytochemistry research group in the Traditional Chinese Medicine research laboratory from Jilin institute of Chinese medicine first successfully isolated the crystalline monomer?– daphnetin?– from the plant. Pharmacological results show that the pharmacological activities of this crystal are equal to Changbai daphne, which suggested the crystal is the main active ingredient . Through the condensation reaction experiment using equimolecular pyrogallic acid, malic acid, and twice the amount of sulfuric acid, under heating reaction, scientists successfully got pale yellow needle daphnetin crystals. From then on artificially synthesized daphnetin has been successfully implemented . A large-scale industrial production can be acquired. The followup researches on the metabolism and pharmacological activity of daphnetin were carried out. In 2009, the State Food and Drug Administration of China approved daphnetin capsule to be used in the clinical.

9.4 Uses: Daphnetin is a natural coumarin derivative providing anti-inflammatory and protective properties to those suffering from lung injury.

9.5 Indications: This product is contained in national standards for chemical drugs, mainly used in Buerger’s disease, occlusive vascular disease, and coronary heart disease.

9.6 General Description: This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

10. Computational chemical data

Molecular Weight: 178.143g/mol
Molecular Formula: C₉H₆O₄
Compound Is Canonicalized: True
XLogP3-AA: 1.2
Exact Mass: 178.02660867
Monoisotopic Mass: 178.02660867
Complexity: 248
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 66.8
Heavy Atom Count: 13
Defined Atom Stereocenter Count: 0
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: AAADcYBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwQAAAAAAAAACBAAAAGgAACAAADASAmAAwDoAABgCIAiDSCAACCAAgIAAIiAAGiMgNJyKGMRqCeiOlwBULuYeA4DwOIAABCAAIQABAAAIQABCAAAAAAAAAAA==

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Daphnetin