基本情報
- CAS
124-20-9- 標準SMILES
NCCCCNCCCN- InChIKey
ATHGHQPFGPMSJY-UHFFFAOYSA-N- 分子式
- C7H19N3
- 平均分子量
- 145.25 g/mol
- 単同位体質量
- 145.15789761
概要
Spermidine is a triamine that is the 1,5,10-triaza derivative of decane. It has a role as an autophagy inducer, a geroprotector and a fundamental metabolite. It is a triamine and a polyazaalkane. It is a conjugate base of a spermidine(3+).
名称と識別子
- 優先名称
- Spermidine
- IUPAC
- N'-(3-aminopropyl)butane-1,4-diamine
- 現地名
- 4-(3-アミノプロピルアミノ)-1-ブタンアミン
- 英語名
- Spermidine
- 分子式
- C7H19N3
- 分子量
- 145.25
名称と別名
名称をさらに表示
データベース識別子
- CAS
124-20-9- PubChem CID
- 1102
- DTXSID
DTXSID4036645- ChEMBL
CHEMBL19612- ChEBI
CHEBI:16610- UNII
- U87FK77H25
- EC Number
- 204-689-0
- Nikkaji
- J10.054D
物性
構造計算による物性
- XLogP
- -1
- 極性表面積
- 64.1 Ų
- 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
実験および物理化学的性質
Melting Point
< 25 °C
< 25 °C
Collision Cross Section
136.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
131.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
136.2 Ų [M+Na]+
物理化学的性質
- 融点
- 23 · 23-25 °C
- 沸点
- 128 · 128-130 °C (14 mmHg)
- 比重(密度)
- 1 g/mL · 1.00 g/mL at 20 °C
- 屈折率
- 20 · n20/D 1.479(lit.)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- room temp
- 溶解性
- 2 O: · H2O: 1M at20℃、透明、無色
- 外見
- 融解後の液体
- 酸解離定数(Pka)
- 10.53 · 10.53±0.19(Predicted)
- 色
- 無色透明
- 比重
- 0.925 · 0.925
- PH
- 12 · 12.0-13.5 (25℃, 1M in H2O)
- 臭い (Odor)
- イクティアル、アンモニア性
- 由来生物
- synthetic
- 水溶解度
- 水、エタノール、エーテルと混和します。
- Merck
- 14 · 14,8742
- BRN
- 1698591 · 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 · 124-20-9(CAS DataBase Reference)
- EPAの化学物質情報
- 1 · 1,4-Butanediamine, N-(3-aminopropyl)- (124-20-9)
化学的性質
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.
安全と法規制
GHS分類
GHS Classification
Danger
H314 (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.
危険有害性情報
毒性情報
Toxicity Summary
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.
安全データ
- F
- 3-10-34
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- EJ7000000
- ridadr
- UN 2735 8/PG 2
- hs_code
- 29212900
- risk_code
- 34
- hazard_code
- C
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- packing_group
- III
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
- ストレージクラス
- 8A - Combustible corrosive hazardous materials
化学と産業
薬理情報
用途と製造
応用分野
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.
調製方法
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
上流・下流製品情報
上流原料
サプライヤー100 社
補足説明
定義ChEBI: Spermidine is a triamine that is the 1,5,10-triaza derivative of decane. It is a polyamine that is routinely included in restriction enzyme digestions to improve the cleavage efficacy of the DNA. Spermidine counteracts the inhibitory effects of contaminants coisolated with DNA and consequently permits complete digestion of the DNA at lower enzyme concentrations.
関連反応
化合物ノート
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