ジペンテンT

Spermine

HCID 1103CAS 68956-56-9

基本情報

標準SMILES
NCCCNCCCCNCCCN
InChIKey
PFNFFQXMRSDOHW-UHFFFAOYSA-N
分子式
C10H26N4
平均分子量
202.34 g/mol
単同位体質量
202.21574683

概要

Spermine is a polyazaalkane that is tetradecane in which the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine has broad actions on cellular metabolism. It has a role as an antioxidant, an immunosuppressive agent and a fundamental metabolite. It is a tetramine and a polyazaalkane. It is a conjugate base of a spermine(4+).

名称と識別子

優先名称
Spermine
IUPAC
N,N'-bis(3-aminopropyl)butane-1,4-diamine
現地名
ジペンテンT
英語名
Dipentene
分子式
C10H16
分子量
136.24

名称と別名

spermine71-44-3musculamineneuridinegerontineSperminN,N'-Bis(3-aminopropyl)-1,4-butanediamineDiaminopropyltetramethylenediamine4,9-Diaza-1,12-dodecanediamineN,N'-Bis(3-aminopropyl)butane-1,4-diamineSpermine, puriss1,4-Bis(aminopropyl)butanediamine
名称をさらに表示
ジペンテンTDipenteneDIPENTENE-CDipentene NOGLIDSOL(R) 175GLIDSOL(R) 140THYME TERPENESGLIDSOL(R) 66-2GLIDSOL(R) 5140RHODINYL TERPENESLIME OIL TERPENES
1,4-Butanediamine, N,N'-bis(3-aminopropyl)-4,9-DiazadodecamethylenediamineGerotineSpermina4,9-Diazadodecane-1,12-diamine2FZ7Y3VOQXActilip sp-911,5,10,14-Tetraazatetradecane

データベース識別子

CAS
68956-56-9、71-44-3
PubChem CID
1103
DTXSID
DTXSID9058781
ChEMBL
CHEMBL23194
ChEBI
CHEBI:15746
UNII
2FZ7Y3VOQX
EC Number
200-754-2
Nikkaji
J5.246I

物性

構造計算による物性

XLogP
-1.1
極性表面積
76.1 Ų
水素結合供与体数
4
水素結合受容体数
4
回転可能結合数
11
重原子数
14

実験および物理化学的性質

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Solubility> 100 mg/mL
Boiling Point150-150 °C
Melting Point29 °C
Physical Description · 2 件

Solid; Absorbs carbon dioxide from air; [Merck Index] Colorless solidified mass or fragments; mp = 28-30 deg C; [Sigma-Aldrich MSDS]

Solid

物理化学的性質

沸点
173 · 173-190°C
比重(密度)
0.85 · 0.850
蒸気圧
6.9 hPa · 6.9hPa at 20℃
屈折率
20 · n20/D 1.469
闪点
42 °C · 42°C
貯蔵温度
Flammables area
化学的性質 · 1 件

化学的特性Dipentene is a terpene clear liquid found in various volatile oils such as cardamon, mace, nutmeg , turpentine oil. Dipentene is mainly composed of limonene, beta phellandrene, myrcene and other terpenes. It is used as a solvent for resins, alkyds and waxes and to make paints, enamels, lacquers and polishes.

安全と法規制

GHS分類

GHS Classification · 4 件

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 76 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

Regulatory Information4,9-Diazadodecamethylenediamine: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary · 1 件

Corrosive; [Merck Index] Oral LD30 (mouse) = 650 mg/kg; Causes lung changes, renal tubular changes, and dehydration in intraperitoneal lethal-dose studies of rats; Causes somnolence and convulsions in oral and subcutaneous lethal-dose studies of mice; Causes hypoglycemia and effects on enzymes and lipids in repeated-dose oral studies of rats; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesSkin Corr. 1C (100%)

毒性情報

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 件

Uremic toxins such as spermine 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). Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation.

Signs and Symptoms · 1 件

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

wgk
3
tsca
TSCA listed
ridadr
UN 2052
毒性
The acute oral LD50 value in rats was reported as 5.3 g/kg (4.6-6.0 g/kg) (Moreno, 1972a). The acute dermal LD50 value for d-limonene was reported as > 5 g/kg (Moreno, 1972b).
hs_code
29021900
risk_code
10-38-43-50/53-65

化学と産業

薬理情報

PharmacodynamicsSpermine is a polyamine. It is an organic molecule that is involved in cellular metabolism.
Mechanism of Action · 1 件

Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation.

Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysSpermidine and Spermine Biosynthesis

用途と製造

Uses · 2 件

Used as a tool in biochemical research; [Merck Index]

For nutritional supplementation, also for treating dietary shortage or imbalance

General Manufacturing Information1,4-Butanediamine, N1,N4-bis(3-aminopropyl)-: ACTIVE
応用分野 · 2 件

天然物の起源Found in a very large number of oils, including oils of lemongrass, citronella, palmarosa, cardamon and bergamot, Siberian pine needle oil and several other essential oils including turpentine oils of various origin (Guenther, 1949).

使用Dipentene (Limonene) is a monoterpene olefin having potential applications in polymer and fuel chemistry. It is also widely used as flavoring and fragrance agent. Dipentene (limonene) is a promising green solvent. Kinetics of the reactions of limonene with OH and OD radicals has been investigated in a low pressure flow tube reactor coupled with a quadrupole mass spectrometer.

調製方法 · 1 件

製造方法Dipentene is a by-product in the manufacture of terpineol and in various synthetic products made from α-pinene or turpentine oil (Arctander, 1969). Dipentene is mainly composed of terpene hydrocarbons. because of its refreshing pine, lime aroma and low cost, dipentene is mainly used as cost effective ingredient for household products.

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

補足説明

定義本品は、次の化学式で表されるテルペンである。

関連反応

23 件

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