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4-Hydroxycoumarin

4-Hydroxycoumarin structure

CAS No:
1076-38-6
Formula:
C9H6O3
Chemical Name:
4-Hydroxycoumarin
Synonyms:
2H-1-Benzopyran-2-one,4-hydroxy-;Coumarin,4-hydroxy-;4-Hydroxy-2H-1-benzopyran-2-one;Benzotetronic acid;4-Coumarinol;4-Hydroxycoumarin;4-Hydroxy-2H-benzo[b]pyran-2-one;NSC 11889;4-Hydroxychromen-2-one;4-Hydroxycoumariin;4-Hydroxy-2H-chromen-2-one;4-Hydroxy-2H-benzopyran-2-one;Naian
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Yellow powder or chunksChEBI: A hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group.

4-hydroxycoumarin is a hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group. It is a conjugate acid of a 4-hydroxycoumarin(1-).

4-Hydroxycoumarin Basic Attributes

Molecular Weight：

162.14

Exact Mass：

162.14

BRN：

129768

EC Number：

214-060-2

UNII：

X954ZLL2RD

NSC Number：

11889

DSSTox ID：

DTXSID8061472

HScode：

29322980

Characteristics

PSA：

46.5

XLogP3：

1.3

Appearance：

Clear colorless to slightly yellow Liquid

Density：

1.1734 (rough estimate)

Melting Point：

206 °C @ Solvent: Water

Boiling Point：

228.82°C (rough estimate)

Flash Point：

165.4±20.7 °C

Refractive Index：

1.4500 (estimate)

Water Solubility：

PRACTICALLY INSOLUBLE

Storage Conditions：

Store below +30°C.

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

26-36

RTECS Number：

DJ3100000

Marks：

Xn,Xi

Hazard note：

Irritant

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (94.9%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 205 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

4-hydroxycoumarin

4-Hydroxycoumarin Use and Manufacturing

Methods of Manufacturing

STR39 Method C--Option 1 (Method 'C-1') A mixture of malonic acid monophenyl ester (10) (1 mmol) and Eaton’s reagent (4 ml) was refluxed at 70°C for 2 h. Ice-cold waterwas then added to this mixture with continuous stirring. The precipitateswere filtered with suction, washed with water, dried and recrystallized from ethanol to afford 4-hydroxy coumarin (11).Yield and mp: 63percent, 217–18 C.42A mixture of phenol (19.8 g, 0.21 mol), anhydrous ZnCl2 (84.8 g, 0.62 mol), POC13 (97 g, 0.63 mol), and malonic acid (22 g, 0.21 mol) was heated at 60-65 °C for 40 h, then the mixture was cooled. After the mixture was decomposed with water, the solid was filtered. The solid was dissolved with 10percent aqueous Na2CO3, then acidified with diluted hydrochloric acid. The crystal was filtered to give the product 2a. 4-Hydroxycoumarin (2a) Yellow solid; yield 41percent, mp 211-213 °C. 1H NMR (300 MHz, DMSO) δ 12.57 (s, 1H, OH), 7.84 (d, J = 7.7 Hz, 1H, coumarin-5-H), 7.67 (dd, J = 11.4, 4.1 Hz, 1H, coumarin-7-H), 7.39-7.29 (m, 2H, coumarin-6, 8-H), 5.62 (s, 1H, coumarin-3-H).Test tube in a nitrogen atmosphere under a tetrahydrofuran (2 mL) and the solvent in the acetylacetonate screen third iron {Fe (acac) 3 5.30 mg, 0.015 mmol} existing under 4-sulfamate coumarin (134.64 mg, 0.5 mmol) and DMPU (576 mg, 9eq) and 1, 3-dimethyl -3, 4, 5, 6-tetrahydro -2 (1H) - pyrimidyl dinon (576.76 mg, 4.5 mmol) and then mixed at 0 normal- It was added butyl magnesium chloride (116.87 mg, 1.0 mmol) slowly to give. If after 10 minutes the starting material is exhausted, then terminate the reaction with 1N HCl and extracted with diethyl ether, and after removing the solvent was separated by column chromatography to give the title compound, 4-butyl-coumarin (70percent).

Uses

4-Hydroxy Coumarin is a plant derived antioxidant, protecting against lipid peroxidation, as well as a potential inhibitor of HIV-1 Integrase.

Manufacturing Info：

2H-1-Benzopyran-2-one, 4-hydroxy-: ACTIVE

Computed Properties

Molecular Weight:162.14
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:162.031694049
Monoisotopic Mass:162.031694049
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:232
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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