4-(3-アミノプロピルアミノ)-1-ブタンアミン
スペルミジン · (3-アミノプロピル)(4-アミノブチル)アミン · 4-(3-アミノプロピルアミノ)-1-ブタンアミン · 4-アザ-1,8-オクタンジアミン · N-(3-アミノプロピル)-1,4-ブタンジアミン · 3-アミノプロピル4-アミノブチルアミン · 4-[(3-アミノプロピル)アミノ]ブタン-1-アミン · 4-アザオクタン-1,8-ジアミン
識別子と物理属性
| CAS No. | 124-20-9 |
|---|---|
| 分子式 | C7H19N3 |
| 平均分子量 | 145.25 g/mol |
| 単同位体質量 | 145.15789761 g/mol |
| SMILES | NCCCCNCCCN |
| InChIKey | ATHGHQPFGPMSJY-UHFFFAOYSA-N |
| PubChem CID | 1102 |
| ChEMBL | CHEMBL19612 |
| ChEBI | CHEBI:16610 |
| EC No. | 204-689-0 |
| DTXSID | DTXSID4036645 |
| 現地名 | 4-(3-アミノプロピルアミノ)-1-ブタンアミン |
化学・物理的性質
| XLogP | -1 |
|---|---|
| 極性表面積 | 64.1 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 7 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 56.8 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 香料 | Fragrance Ingredient (1,4-Butanediamine, N-(3-aminopropyl)-) -> IFRA transparency List |
| 融点 | < 25 °C23-25 °C |
| Physical Description | Solid |
| Collision Cross Section | 136.5 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]131.9 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]136.2 Ų [M+Na]+ |
| 沸点 | 128-130 °C (14 mmHg) |
| 密度 | 1.00 g/mL at 20 °C |
| 屈折率 | n20/D 1.479(lit.) |
| 引火点 | >230 °F |
| 貯蔵条件 | room temp |
| 溶解度 | H2O: 1M at20℃、透明、無色水、エタノール、エーテルと混和します。 |
| 外観・状態 | 融解後の液体 |
| pKa（酸解離定数） | 10.53±0.19(Predicted) |
| 色 | 無色透明 |
| 比重 | 0.925 |
| pH | 12.0-13.5 (25℃, 1M in H2O) |
| 臭い | イクティアル、アンモニア性 |
| 由来生物 | synthetic |
| Merck | 14,8742 |
| BRN | 1698591 |
| 安定性 | 安定していますが、空気に敏感で吸湿性が高く、アルゴン下で保管してください。酸、酸塩化物、酸無水物、および酸化剤とは混和しません。 |
| 化粧品成分の機能 | 抗酸化物質ヘアコンディショニング |
| InChI | 1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2 |
| InChIKey | ATHGHQPFGPMSJY-UHFFFAOYSA-N |
| SMILES | NCCCCNCCCN |
| CAS データベース | 124-20-9(CAS DataBase Reference) |
| EPAの化学物質情報 | 1,4-Butanediamine, N-(3-aminopropyl)- (124-20-9) |
化学的特性
Spermidine solution is a colorless clear liquid with very hygroscopic and oxidizable. It is soluble in water (50 mg/ml), ethanol, and ether.
安全性と法規制
| GHS 分類 | DangerH314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 83 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Spermidine: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Corr. 1A (100%) |
| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
| 健康影響 | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| 暴露経路 | Endogenous, Ingestion, Dermal (contact) |
| 毒性の概要 | Uremic toxins such as spermidine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869). |
| Signs and Symptoms | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 3-10-34 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | EJ7000000 |
| 輸送番号（UN） | UN 2735 8/PG 2 |
| 税関コード | 29212900 |
| 危険文句（R） | 34 |
| 危険表示 | C |
| 安全措置（S） | 26-36/37/39-45-27 |
| 危険等級 | 8Eye Dam. 1Skin Corr. 1B |
| 包装等級 | III |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
用途
解説
すべての生体中に存在するポリアミンの一種．N-(3-アミノプロピル)-1,4-ブタンジアミン．DNA二重らせん構造の安定化と変化，RNAの安定化，RNAやDNAポリメラーゼの活性化などの生理作用を示す．
説明
Spermidine is an endogenous polyamine. It is formed from putrescine by spermidine synthase.
製法・合成法
製造方法
The linker resin 2 was used in the synthesis of spermidine. In order to initiate the preparation the 2-nitrossulfonamide was anchored on the resin 2 by reaction in THF under reflux. The resulting resin 3 then reacted with 4-bromobutylphthalimide in acetonitrile in the presence of Cs2CO3 as base, generating the resin 4. Protected spermidine 5 was cleaved from resin 4 after treatment with hydrate hydrazine at room temperature. Spermidine 5 was previously prepared by our group in solution system utilizing Fukuyama's sulfonamide.Synthesis and Characterization of a Linker for Primary Amines used in the Solid Phase Organic Synthesis of SpermidineJ. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011DOI: 10.1590/S0103-50532011000100011