기본 정보
- 표준 SMILES
NCCCNCCCCNCCCN- InChIKey
PFNFFQXMRSDOHW-UHFFFAOYSA-N- 분자식
- C10H26N4
- 평균 분자량
- 202.34 g/mol
- 단동위원소 질량
- 202.21574683
개요
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+).
이름 및 식별자
- 우선 이름
- Spermine
- IUPAC
- N,N'-bis(3-aminopropyl)butane-1,4-diamine
- 현지명
- 파라-멘타디엔
- 영어명
- Dipentene
- 분자식
- C10H16
- 분자량
- 136.24
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- 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
물성
구조 계산 물성
- XLogP
- -1.1
- 극성 표면적
- 76.1 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 11
- 무거운 원자 수
- 14
- 형식 전하
- 0
- 복잡도
- 86.1
실험 및 물리화학적 성질
Physical Description
Solid; Absorbs carbon dioxide from air; [Merck Index] Colorless solidified mass or fragments; mp = 28-30 deg C; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
154.57 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
151.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
148.2 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
151.4 Ų [M+Na]+
물리화학적 성질
- 끓는 점
- 173 · 173-190°C
- 밀도
- 0.85 · 0.850
- 증기압
- 6.9 hPa · 6.9hPa at 20℃
- 굴절률
- 20 · n20/D 1.469
- 인화점
- 42 °C · 42°C
- 저장 조건
- Flammables area
- 물리적 상태
- 액체
- 색상
- 투명한
- 냄새
- 100 %에서 · 100.00%에서. 소나무 감귤류 허브 그린
- 냄새 유형
- 소나무
- 수용성
- 2.75 mg/L · 2.75mg/L at 20℃
- 비열
- 1.83 J/ · Cp(liquid): 1.83 J/(g·K), at 25℃
- Dielectric constant
- 2.3 · 2.3(20℃)
- 화장품 원료 기능
- 향수
- LogP
- 4.46 at · 4.46 at 20℃
- EPA
- Hydrocarbons, terpene processing by-products (68956-56-9)
화학적 성질
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.
안전 및 규제
GHS 분류
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 76 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazards Summary
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]
독성 정보
Toxicity Summary
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
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.
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2052
- 독성
- 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 번호
- 29021900
- risk_code
- 10-38-43-50/53-65
- hazard_code
- Xi,N
- safety_code
- 24-37-60-61-2
- 포장분류
- III
- 위험 등급
- 3
- 기존화학 물질
- KE-20100
화학 및 산업
약리 정보
Mechanism of Action
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.
용도 및 제조
Uses
Used as a tool in biochemical research; [Merck Index]
For nutritional supplementation, also for treating dietary shortage or imbalance
응용 분야
출처Found 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).
용도Dipentene (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.
제조 방법
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.
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