스페르미딘

스페르미딘
스페르미딘 구조식 이미지
카스 번호:
124-20-9
한글명:
스페르미딘
동의어(한글):
스페르미딘
상품명:
Spermidine
동의어(영문):
SperMidin;N1-(3-AMINOPROPYL)BUTANE-1,4-DIAMINE;Spermidine-Rich Wheat Germ Extract;1,4-Butanediamine, N-(3-aminopropyl)-;3.2 Kg;Spermidie;Spemidine;SPERMIDINE;SPERMIDINE(RG);Spermidine,99%
CBNumber:
CB2165662
분자식:
C7H19N3
포뮬러 무게:
145.25
MOL 파일:
124-20-9.mol
MSDS 파일:
SDS

스페르미딘 속성

녹는점
23-25 °C
끓는 점
128-130 °C (14 mmHg)
밀도
1.00 g/mL at 20 °C
굴절률
n20/D 1.479(lit.)
인화점
>230 °F
저장 조건
room temp
용해도
H2O: 1 M at 20 °C, 투명, 무색
산도 계수 (pKa)
10.53±0.19(Predicted)
물리적 상태
녹은 후에 액체
색상
무색의
Specific Gravity
0.925
수소이온지수(pH)
12.0-13.5 (25℃, 1M in H2O)
냄새
익티알, 암모니아성
수용성
물, 에탄올, 에테르와 혼합 가능.
감도
Air Sensitive
최대 파장(λmax)
λ: 260 nm Amax: 0.1
λ: 280 nm Amax: 0.05
Merck
14,8742
BRN
1698591
안정성
안정적이지만 공기에 민감하고 흡습성이 매우 높으므로 아르곤 상태로 보관하십시오. 산, 산 염화물, 산 무수물, 산화제와 호환되지 않습니다.
InChIKey
ATHGHQPFGPMSJY-UHFFFAOYSA-N
CAS 데이터베이스
124-20-9(CAS DataBase Reference)
EPA
1,4-Butanediamine, N-(3-aminopropyl)- (124-20-9)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 C
위험 카페고리 넘버 34
안전지침서 26-36/37/39-45-27
유엔번호(UN No.) UN 2735 8/PG 2
WGK 독일 3
RTECS 번호 EJ7000000
F 고인화성물질 3-10-34
TSCA Yes
위험 등급 8
포장분류 III
HS 번호 29212900
기존화학 물질 KE-01572
그림문자(GHS): GHS hazard pictograms
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H314 피부에 심한 화상과 눈에 손상을 일으킴 피부부식성 또는 자극성물질 구분 1A, B, C 위험 GHS hazard pictograms P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
예방조치문구:
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P303+P361+P353 피부(또는 머리카락)에 묻으면 오염된 모든 의복은 벗거나 제거하시오 피부를 물로 씻으시오/샤워하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P363 다시 사용전 오염된 의류는 세척하시오.
P405 밀봉하여 저장하시오.
NFPA 704
1
3 1

스페르미딘 C화학적 특성, 용도, 생산

개요

Spermidine is an endogenous polyamine. It is formed from putrescine by spermidine synthase.

화학적 성질

Spermidine solution is a colorless clear liquid with very hygroscopic and oxidizable. It is soluble in water (50 mg/ml), ethanol, and ether.

Source

Spermidine is found in fresh green pepper, wheat germ, cauliflower, broccoli, mushrooms, and a variety of cheeses. Even higher amounts are found in soybean products such as natto, shitake mushrooms, amaranth grain and durian. Some of these ingredients are particularly common in a Mediterranean diet, which may explain why some believe eating like the Spanish can prolong your life.

주요 응용

Spermidine serves as a precursor of spermine and essential for both normal and neoplastic tissue growth. It was first detected in human sperm, but occurs widely in nature. It is essential in both normal and neoplastic tissue growth. Spermidine has a role in cell growth processes and the formation and interconversion of spermidine in mammalian cells has been reported. It has been studied in the regulation of tRNA methyltransferase activity and stimulates T4 polynucleotide kinase activity.

정의

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.

제조 방법

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 of spermidine
Synthesis and Characterization of a Linker for Primary Amines used in the Solid Phase Organic Synthesis of Spermidine
J. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011
DOI: 10.1590/S0103-50532011000100011

Origin

Spermidine was first discovered in 1678 by Dutch scientist Anton Van Leeuwenhoek in a sample of human semen. Shortly after, spermidine was discovered in human sperm. In the body, spermidine is created from its precursor putrescine.

benefits

The biggest benefit of spermidine is its ability to reduce age-related diseases. It benefits cardioactive, spermidine can reduce the development of atherosclerosis in mice by reducing inflammation and improving cellular (mitochondria) function. It can reduce the formation of blood clots (platelet aggregation) and improve the normal dilation of cells lining blood vessels. Spermidine lowers blood pressure, improves energy use, and reduces heart cell death. It prevents neurologic diseases, and spermidine helps reduce cognitive, memory, and functional impairment associated with aging. It can also Decrease blood sugar levels, Increase autophagy, Increase bone strength, and have Anti-inflammatory effects.

Mode of action

Spermidine's main mechanism of action is its ability to induce autophagy, a self-preservation process which clears out toxic, damaged and dysfunctional cells, resulting in lower levels of inflammation in the body. Autophagy is the main mechanism of spermidine in delaying aging and prolonging the lifespan. In addition, spermidine exerts its effects through other mechanisms, including anti-inflammation, histone acetylation reduction, lipid metabolism and regulation of cell growth and signaling pathways.

참고 문헌

Madeo, F., Eisenberg, T., Pietrocola, F., et al. Spermidine in health and disease. Science 359(6374), eaan2788 (2018).
Lopatin, A.N., Makhina, E.N., and Nichols, C.G. Potassium channel block by cytoplasmic polyamines as the mechanism of intrinsic rectification. Nature 372(6504), 366-369 (1994).
Eisenberg, T., Knauer, H., Schauer, A., et al. Induction of autophagy by spermidine promotes longevity. Nat. Cell Biol. 11(11), 1305-1314 (2009).
Guo, X., Harada, C., Namekata, K., et al. Spermidine alleviates severity of murine experimental autoimmune encephalomyelitis. Invest. Ophthalmol. Vis. Sci. 52(5), 2696-2703 (2011).
Eisenberg, T., Abdellatif, M., Schroeder, S., et al. Cardioprotection and lifespan extension by the natural polyamine spermidine. Nat. Med. 22(12), 1428-1438 (2016).

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