스핑가닌

한글명:스핑가닌

카스 번호3102-56-5

상품명:DL-erythro-Dihydrosphingosine

CBNumberCB6139144

분자식C18H39NO2

포뮬러 무게301.51

MOL 파일3102-56-5.mol

동의어(한글)

스핑가닌

화학적 성질

녹는점	70-72°C
끓는 점	446.2±25.0 °C(Predicted)
밀도	0.927±0.06 g/cm3(Predicted)
저장 조건	−20°C
용해도	클로로포름/메탄올(9:1): 20mg/mL, 투명, 무색 ~ 희미한 노란색
물리적 상태	고체
물리적 상태	단단한 모양
산도 계수 (pKa)	12.57±0.45(Predicted)
색상	하얀색
수용성	물에 용해됨(일부 혼화성), 클로로포름, 100% 따뜻한 에탄올(25mg/ml), 따뜻한 DMSO(25mg/ml) 및 메탄올.
InChI	InChI=1/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/s3
InChIKey	OTKJDMGTUTTYMP-LHIQYTEENA-N
SMILES	C(O)[C@@H](N)[C@@H](O)CCCCCCCCCCCCCCC \|&1:2,4,r\|
CAS 데이터베이스	3102-56-5(CAS DataBase Reference)

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스핑가닌 화학적 특성, 용도, 생산

개요
DL-erythro Sphinganine (d18:0) is a precursor of ceramide and sphingosine as well as a substrate of sphingosine kinases, which generate sphinganine-1-phosphate . Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins as well as in some cancers. This product is a mixture of sphinganine (d18:0) , L-erythro sphinganine (d18:0) , D-threo sphinganine (d18:0) , and L-threo sphinganine (d18:0). [Matreya, LLC. Catalog No. 1324]
화학적 성질
White Powder
용도
DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.
Biological Functions
Sphingosine (Sph) is emerging as an intracellular regulator of cellular differentiation and apoptosis. Three stereoisomers,d-erythro-Sph,l-threo-Sph, and dl-erythro-dihydrosphingosine, were tested in the induction of apoptosis and inhibition of MAPK activity in three different kinds of solid tumour cell lines. d-erythro-Sph was strongest in these effects among the three compounds. l-threo-Sphingosine was partly active. On the other hand,dl-erythro-dihydrosphingosine was inactive[1].
생물학적 활성
Protein kinase C inhibitor.
Purification Methods
Purify it by recrystallisation from pet ether/EtOAc or CHCl3. The (±)-N-dichloroacetyl derivative has m 142-144o (from MeOH). [Shapiro et al. J Am Chem Soc 80 2170 1958, Shapiro & Sheradsky J Org Chem 28 2157 1963.] The D-isomer crystallises from pet ether/Et2O and has m 78.5-79o, [] 28 +6o (CHCl3/MeOH, 10:1). [Grob & Jenny Helv Chim Acta 35 2106 1953, Jenny & Grob Helv Chim Acta 36 1454 1953, Beilstein 4 I 448, 4 II 757, 4 III 854, 4 IV 1887.]

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