フザリン酸
5-ブチルピコリン酸 · フサリニン酸 · 5-ブチルピリジン-2-カルボン酸 · 5-ブチル-2-ピリジンカルボン酸 · フサリン酸 · フサル酸 · フザリン酸 · Fusaric
識別子と物理属性
| CAS No. | 536-69-6 |
|---|---|
| 分子式 | C10H13NO2 |
| 平均分子量 | 179.22 g/mol |
| 単同位体質量 | 179.09462866 g/mol |
| SMILES | CCCCc1ccc(C(=O)O)nc1 |
| InChIKey | DGMPVYSXXIOGJY-UHFFFAOYSA-N |
| PubChem CID | 3442 |
| ChEMBL | CHEMBL24510 |
| ChEBI | CHEBI:5199 |
| EC No. | 208-643-0 |
| DTXSID | DTXSID5023085 |
| 現地名 | フザリン酸 |
化学・物理的性質
| XLogP | 2.6 |
|---|---|
| 極性表面積 | 50.2 |
| 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 | 4 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 170 |
| Color/Form | COLORLESS CRYSTALS |
| 融点 | 96-98 °C96-100 °C |
| 沸点 | 311.75°C (rough estimate) |
| 密度 | 1.1248 (rough estimate) |
| 屈折率 | 1.5710 (estimate) |
| 貯蔵条件 | Inert atmosphere,Store in freezer, under -20°C |
| 溶解度 | エタノール: 50 mg/mL、透明、微黄色 |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | 1.11±0.50(Predicted) |
| 色 | オフホワイトからかすかな黄色 |
| Merck | 14,4314 |
| BRN | 125804 |
| InChI | 1S/C10H13NO2/c1-2-3-4-8-5-6-9(10(12)13)11-7-8/h5-7H,2-4H2,1H3,(H,12,13) |
| InChIKey | DGMPVYSXXIOGJY-UHFFFAOYSA-N |
| SMILES | CCCCc1ccc(nc1)C(O)=O |
| LogP（分配係数） | 1.960 (est) |
| CAS データベース | 536-69-6(CAS DataBase Reference) |
| EPAの化学物質情報 | 2-Pyridinecarboxylic acid, 5-butyl- (536-69-6) |
化学的特性
off-white to faint yellowish crystalline powder
安全性と法規制
| GHS 分類 | WarningH302 (98.6%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 2 notifications to the ECHA C&L Inventory.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. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Special Reports | A REVIEW WITH 28 REFERENCES OF THE ROLE OF FUSARIC ACID AS A PLANT TOXIN.[KALYANASUNDARAM RMODE OF ACTION OF FUSARIC ACIDPLANT DIS PROBL PROC INT SYMP 1ST: 142 (1970)] |
| Hazard Classes and Categories | Acute Tox. 4 (98.6%) |
| Treatment | Natamycin ophthalmic suspension is the drug of choice for filamentous fungal infections such as mycotic keratitis. (L1964) |
| 相互作用 | WHEN FUSARIC ACID (100 MG/KG, IP) WAS ADMIN TO MALE MICE 6 HR AFTER ALCOHOL WITHDRAWAL, BRAIN NORADRENALINE, DOPAMINE, & SEROTONIN CONCN WERE 112.8, 186.4, & 652.8 NG/G 4 HR LATER. FUSARIC ACID ADMIN DECREASED BRAIN NORADRENALINE LEVEL ACCOMPANIED BY AN ENHANCED ALCOHOL WITHDRAWAL SYNDROME. |
| 健康影響 | Fusaric acid can contribute to mycotic keratitis infections. It also has developmental and neurological effects. (A3021, A3023) |
| 暴露経路 | Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) |
| 毒性の概要 | Fusaric acid affects neurotransmitter levels by acting as a partial inhibitor on tyrosine-hydroxylase and an inhibitor on dopamine-beta-hydroxylase. This has been shown to cause elevated serotonin, 5-hydroxyindoleacetic acid, tyrosine, and dopamine levels in the brain, as well as decreased norepinephrine levels. These changes in neurotransmitter levels may be responsible for effects such as hypotension, altered behavior and locomotive activity, neurological disorders, and developmental problems. (A3020, A3021, A3022, A3023) |
| Signs and Symptoms | Fusaric acid can cause vomiting, hypotension, and alterations in behavioral and locomotive activity. (A3020, A3022, A3023) |
用途
解説
5-butyl-2-pyridinecarboxylic acid．C10H13NO2(179.12)．フザリン酸は，イネの馬鹿苗病菌Gibberella fujikuroiの代謝産物．無色の板状晶．融点108 ℃．イネ苗の無秩序な伸長を抑制する作用があり，またチフス菌に対して発育阻止作用がある．最近，ドーパミン-β-ヒドロキシラーゼの阻害作用があり，組織中のノルアドレナリンを減少させ，動物に顕著な血圧降下作用を示すとともに，ヒトの高血圧症の降圧剤として有効であることが見いだされた．森北出版「化学辞典（第2版）
使用
Fusaric acid may be used as a derivatizing reagent for the quantification of hydroxysteroids and dehydroepiandrosterone (DHEA)and sulfated DHEA in biological samples using liquid chromatography electrospray-ionization-tandem mass spectrometry (LC/ESI-MS/MS) technique.
一般的な説明
Fusaric acid is a novel proton-affinitive derivatizing agent, having an ionization moiety and a hydrophobic moiety. It is commonly used for the derivatization of alcohols and phenols, by liquid chromatography coupled with electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS).
製法・合成法
純化方法
Dissolve it in CHCl3, dry (Na2SO4), filter, evaporate and recrystallise the residue from 50 parts of pet ether (b 40-60o), CHCl3/pet ether or EtOAc, then sublime it in vacuo. The amide crystallises from MeOH with m 128.2-129.0o. The copper salt forms bluish violet crystals from H2O and has m 258-259o. [Hardegger & Nikles Helv Chim Acta 39 505 1956, Schreiber & Adam Chem Ber 93 1848 1960, NMR and MS: Tschesche & Führer Chem Ber 111 3500 1978, Beilstein 22 III/IV 764, 22/2 V 384.]