4-メチルウンベリフェロン

4-Methylumbelliferone

HCID 5280567

基本情報

CAS
90-33-5
標準SMILES
Cc1cc(=O)oc2cc(O)ccc12
InChIKey
HSHNITRMYYLLCV-UHFFFAOYSA-N
分子式
C10H8O3
平均分子量
176.17 g/mol
単同位体質量
176.04734412

概要

Beta-methylumbelliferone appears as colorless crystals. Insoluble in water. (NTP, 1992)

名称と識別子

優先名称
4-Methylumbelliferone
IUPAC
7-hydroxy-4-methylchromen-2-one
現地名
4-メチルウンベリフェロン
英語名
4-Methylumbelliferone
分子式
C10H8O3
分子量
176.17

名称と別名

4-methylumbelliferoneHymecromone90-33-57-Hydroxy-4-methyl-2H-chromen-2-oneImecromoneCantabilineCrodimonCholonertonHymecromonHimecromonaHymecromonumResocyanine
名称をさらに表示
4-メチルウンベリフェロン7-ヒドロキシ-4-メチル-2H-1-ベンゾピラン-2-オンカンタビリン4-メチル-7-ヒドロキシ-2H-1-ベンゾピラン-2-オンパイロット447ヒメコールイメクロモンオメガ1277-ヒドロキシ-4-メチルクマリンハイメクロモン4-メチル-7-ヒドロキシクマリンコレスチルクロディモントリデモンエーデシン·Cメチルウンベリフェロンヒメクロモンメンジアキソンβ-メチルウンベリフェロンクマリン47-HYDROXY-4-METHYLCOUMARIN4-MU4-METHYL-7-HYDROXYCOUMARIN7-HYDROXY-4-METHYL-CHROMEN-2-ONE4-MethylumbelliferonBMUMedillaBilcolic
2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-7-Hydroxy-4-methyl-2H-1-benzopyran-2-one7-hydroxy-4-methylchromen-2-one7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyranLM-947-hydroxy-4-methyl-coumarin7-Hydroxy-4-methyl-2-oxo-3-chromeneDTXSID8025670

データベース識別子

CAS
90-33-5
PubChem CID
5280567
DTXSID
DTXSID8025670
ChEMBL
CHEMBL12208
ChEBI
CHEBI:17224
UNII
3T5NG4Q468
EC Number
201-986-7
Nikkaji
J1.763.999D、J3.914D

物性

構造計算による物性

XLogP
1.9
極性表面積
46.5 Ų
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
13

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Other Aromatic Compounds

Industrial compound

Drugs · 2 件

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

SpringerMaterials PropertiesAngular frequency
LogP1.9
SolubilityInsoluble (NTP, 1992)
Melting Point381 to 383 °F (NTP, 1992)

物理化学的性質

融点
188.5 · 188.5-190 °C(lit.)
沸点
267.77 °C · 267.77°C (rough estimate)
比重(密度)
1.1958 · 1.1958 (rough estimate)
屈折率
1.5036 · 1.5036 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
水にほとんど溶けず、エタノール、エーテル、クロロホルムに溶けにくく、メタノールに溶ける。

化学的性質

化学的特性Off-white to yellow crystals. Soluble in ethanol, acetic acid, alkali solutions, and ammonia. Slightly soluble in hot water, ether, and chloroform. Exhibits blue fluorescence when exposed to concentrated sulfuric acid.

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 340 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

Chemical: 2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-

2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include local irritation of the skin, eyes and mucous membranes.
Hazards Summary · 1 件

An irritant; [NTP] Causes tearing, ptosis, and altered sleep time in oral lethal-dose studies of mice and rats; Causes changes in liver and pituitary weights in 26-week constant oral studies of rats; [RTECS] An irritant; Harmful by inhalation and skin absorption; [Acros Organics MSDS]

Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Air and Water ReactionsInsoluble in water.

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 件

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

安全データ

wgk
2
tsca
TSCA listed
rtecs
GN7000000
毒性
LD50 oral in rat: 3850mg/kg
hs_code
29329990
risk_code
36/37/38-20/21/22

化学と産業

薬理情報

ATC Code · 2 件

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Metabolism/Metabolites4-Methylumbelliferone has known human metabolites that include 4-Methylumbelliferone O-glucuronide.
MeSH Pharmacological Classification · 1 件

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

用途と製造

Uses · 2 件

Used as an analytical reagent, fluorescent indicator, and antispasmodic drug; [Merck Index] Used in tunable lasers; [NTP]

Use (kg; approx.) in Germany (2009): >2500

General Manufacturing Information2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-: ACTIVE
応用分野 · 3 件

用途硝酸イオンの比色定量試薬。蛍光指示薬。

使用4-methylumbelliferone (4-MU) is a dietary supplement that inhibits hyaluronic acid (HA) synthesis. HA is a prominent component of the extracellular matrix at many sites of chronic inflammation, including type 1 diabetes (T1D), multiple sclerosis, and numerous malignancies. 4-MU is an already approved drug in Europe and Asia called “hymecromone” where it is used to treat biliary spasm.

一般的な説明4-Methylumbelliferone is a useful indicator for nitric acid determination and enzyme activity investigation. It emits fluorescence in alkaline solution and Standard for the fluorometric determination of enzyme activity. Highly fluorescent in alkaline solution. Fluorescence: max Abs. l = 360nm, max. Em. l = 449nm; pH > 9.

調製方法 · 2 件

製造方法4-Methylumbelliferone is obtained by the cyclization reaction between resorcinol and ethyl acetate. Concentrated sulfuric acid is cooled to below 10 ° C, and a solution prepared from resorcinol and ethyl acetate is slowly added to the stirring solution. After dropping it completely, let it stand for 12 hours. Then, the reaction mixture is added into ice-cold water. The precipitate is filtered out and purified with a dilute sodium hydroxide solution and dilute sulfuric acid to obtain the final product.

純化方法Purify it by recrystallisation from EtOH. It is very slightly soluble in cold H2O (solubility at 37o is 0.22%), slightly soluble in Et2O and CHCl3, but soluble in MeOH and AcOH. It has a blue fluorescence in aqueous EtOH and has UV: 221, max 251 and 322.5nm (MeOH). The IR has 3077 br, 1667, 1592, 1385, 1267, 1156, 1130 and 1066 cm-1.max The acetate has m 153-154o. [Woods & Sapp J Org Chem 27 3703 1962, Beilstein 18 III/IV 332, 18/1 V 439.]

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上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
補足説明 · 1 件

定義ChEBI: 4-methylumbelliferone is a hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4. It has a role as an antineoplastic agent and a hyaluronic acid synthesis inhibitor. It is functionally related to an umbelliferone.

関連反応

54 件

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