4-Hydroxycoumarin (HCID 54682930)

概要

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-).

名称と識別子

優先名称: 4-Hydroxycoumarin
IUPAC: 4-hydroxychromen-2-one
現地名: 4-ヒドロキシクマリン
英語名: 4-Hydroxycoumarin
分子式: C9H6O3
分子量: 162.14

名称と別名

4-Hydroxycoumarin1076-38-64-CoumarinolBenzotetronic acid4-hydroxychromen-2-oneCoumarin, 4-hydroxy-4-Hydroxy-2H-1-benzopyran-2-one2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-4-hydroxy-2-chromenoneX954ZLL2RDNSC-11889DTXSID8061472

名称をさらに表示

4-ヒドロキシクマリンベンゾテトロン酸4-クマリノール4-ヒドロキシ-2H-1-ベンゾピラン-2-オン4‐ヒドロキシクマリン4-ヒドロキシクマリン, 98+%ヒドロキシクマリン, 4-HydroxyCoumarin4-Coumaryl alcohol4-hydroxy-2h-1-benzopyran-2-onCOUMARINOL4-(3-hydroxyprop-1-enyl)phenolCOUMARIN KIT4-HydroxycouMa

4-hydroxy-2H-benzo[b]pyran-2-oneCHEBI:400704-hydroxy-2H-benzo(b)pyran-2-one4-OH coumarinRefChem:388756DTXCID1033086214-060-24-Hydroxy-2H-chromen-2-one

データベース識別子

CAS: 1076-38-6、22105-09-5
PubChem CID: 54682930
DTXSID: DTXSID8061472
ChEMBL: CHEMBL301141
ChEBI: CHEBI:40070
UNII: X954ZLL2RD
EC Number: 214-060-2
Nikkaji: J12.175D、J942.074F

物性

構造計算による物性

XLogP: 1.3
極性表面積: 46.5 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 0
重原子数: 12
形式電荷: 0
複雑度: 232

実験および物理化学的性質

Chemical ClassesBiological Agents -> Plant Toxins

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesChemical shift

LogP1.42

Physical DescriptionBeige powder; [Sigma-Aldrich MSDS]

物理化学的性質

融点: 211 · 211-213 °C (lit.)
沸点: 228.82 °C · 228.82°C (rough estimate)
比重(密度): 1.1734 · 1.1734 (rough estimate)
蒸気圧: 0.02 Pa · 0.02Pa at 25℃
屈折率: 1.45 · 1.4500 (estimate)
貯蔵温度: 30 °C · Store below +30°C.
溶解性: DMSO（微量）、メタノール（微量）
酸解離定数(Pka): 4.5 · 4.50±1.00(Predicted)
外見: 液体
色: 無色透明～微黄色透明
臭い (Odor): Very faint woody-medicinal odor with a with Aluminum chloride. nut-like, hcrbaccous tone
水溶解度: 実質的に不溶
BRN: 129768 · 129768
InChI: 1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
InChIKey: VXIXUWQIVKSKSA-UHFFFAOYSA-N
SMILES: OC1=CC(=O)Oc2ccccc12
LogP: 1.6 · 1.6-2.31 at 21.2℃
CAS データベース: 1076 · 1076-38-6(CAS DataBase Reference)
NISTの化学物質情報: 4 · 4-Hydroxycoumarin(1076-38-6)
EPAの化学物質情報: 2 H-1-Benzopyran-2-one, · 2H-1-Benzopyran-2-one, 4-hydroxy- (1076-38-6)

化学的性質

化学的特性Yellow powder or chunks or Slightly yellow needle-like crystals. freely soluble in ethanol, ether and hot water. brown in color with ferric chloride.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 5.1% (13 of 254) of reports.

Warning

H302 (90.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 254 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 3 件

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

Status: Active Update: 07-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32315

2H-1-Benzopyran-2-one, 4-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Closely related to coumarin, the parent compound of anticoagulants such as warfarin; Studies using frog embryo assays demonstrated half the potency of coumarin in producing teratogenic effects; [REPROTOX] Causes somnolence and muscle contraction or spasticity in subcutaneous lethal-studies of mice; Causes effects on inflammation in 4-day intermittent oral studies rats; [RTECS] An irritant; Harmful by ingestion; [Sigma-Aldrich MSDS] See Coumarin.

Hazard Classes and CategoriesAcute Tox. 4 (90.9%)

安全データ

wgk: 3
tsca: TSCA listed
rtecs: DJ3100000
hs_code: 29322980
risk_code: 22-36/37/38
化審法: 新規公示化学物質（2011年3月31日以前届出）
hazard_code: Xn,Xi
hazard_note: Irritant
safety_code: 26-36
Hazard Classifications: Acute Tox. 4 Oral
ストレージクラス: 11 - Combustible Solids

化学と産業

用途と製造

General Manufacturing Information2H-1-Benzopyran-2-one, 4-hydroxy-: ACTIVE

応用分野 · 3 件

用途有機合成原料。

使用4-Hydroxycoumarin is a plant derived antioxidant, protecting against lipid peroxidation, as well as a potential inhibitor of HIV-1 Integrase. 4-Hydroxycoumarins are a very important class of biologically active drugs which are widely used as anticoagulants-Warfarin and Acenocoumarol.

使用4-Hydroxycoumarin may be regarded as a phenylenetetronic acid , and like tetronic acid forms condensation products with aldehydes. Synthesis of biscoumarin derivatives by the reaction of aldehydes and 4-hydroxycoumarin using ruthenium(III) chloride hydrate as a versatile homogeneous catalyst.

調製方法

純化方法Crystallise 4-hydroxycoumarin from water and dry it in a vacuum desiccator over pKEst Sicapent. [Beilstein 18/1 V 378.]

サプライヤー50 社

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補足説明

定義ChEBI: 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-ヒドロキシクマリン

基本情報

概要