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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 257
実験および物理化学的性質
Chemical Classes
Other Classes -> Other Aromatic Compounds
Industrial compound
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
Physical Description
Beta-methylumbelliferone appears as colorless crystals. Insoluble in water. (NTP, 1992)
Colorless solid; [CAMEO] Off-white powder; [Acros Organics MSDS]
Solid
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。
- 外見
- 結晶性粉末
- 酸解離定数(Pka)
- 7.79 · 7.79(at 25℃)
- 色
- オフホワイトからイエロー
- 水溶解度
- わずかに溶ける
- Merck
- 14 · 14,4854
- BRN
- 142217 · 142217
- 安定性
- 安定。可燃性。強力な酸化剤とは相容れない。
- 主な用途
- カラーフィルター、エレクトロルミネッセンスディスプレイ、文書セキュリティプロセス、レーザー、集積回路、液晶ディスプレイ、表面光沢組成物、油性製品、歯のホワイトニング剤、リソソーム酵素アッセイ、リパーゼ基質、生細胞におけるタンパク質間相互作用の決定、抗トリパノソーマ薬、抗リーシュマニア薬、抗がん剤、抗HIV薬、抗マラリア薬、抗菌剤、抗真菌剤
- InChI
- 1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
- InChIKey
- HSHNITRMYYLLCV-UHFFFAOYSA-N
- SMILES
- CC1=CC(=O)Oc2cc(O)ccc12
- LogP
- 2.37 · 2.370 (est)
- CAS データベース
- 90 · 90-33-5(CAS DataBase Reference)
- NISTの化学物質情報
- 7 · Coumarin, 7-hydroxy-4-methyl-(90-33-5)
- EPAの化学物質情報
- 4 · 4-Methylumbelliferone (90-33-5)
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
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
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
Hazards Summary
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]
安全と保護具
First Aid
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
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)
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
- 化審法
- (9)-1048
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 26-37/39-36
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
MeSH Pharmacological Classification
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
Used as an analytical reagent, fluorescent indicator, and antispasmodic drug; [Merck Index] Used in tunable lasers; [NTP]
Use (kg; approx.) in Germany (2009): >2500
応用分野
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
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー100 社
補足説明
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
化合物ノート
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