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(2S,3R,E)-2-Amino-4-heptadecene-1,3-diol

Product Name(2S,3R,E)-2-Amino-4-heptadecene-1,3-diol
CAS6918-48-5
MFC17H35NO2
MW285.47
EINECS
MOL File6918-48-5.mol

Chemical Properties

Boiling point	432.9±45.0 °C(Predicted)
Density	0.944±0.06 g/cm3(Predicted)
storage temp.	-20°C
solubility	DMF: 10 mg/ml; DMSO: 2 mg/ml; Ethanol: Miscible
form	A crystalline solid
pka	11.80±0.45(Predicted)
color	White to off-white
InChI	1S/C17H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)16(18)15-19/h13-14,16-17,19-20H,2-12,15,18H2,1H3/b14-13+/t16-,17+/m0/s1
InChIKey	RBEJCQPPFCKTRZ-LHMZYYNSSA-N
SMILES	OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCC

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Sphingosine is an amino alcohol most commonly characterized by an 18-carbon unsaturated hydrocarbon chain sphingosine (d18:1) . However, the hydrocarbon chain length of sphingosine, and the related dihydrosphingosine, can vary from 12-26 carbons in mammalian tissues. Sphingosine (d17:1) is a naturally-occurring but uncommon form of sphingosine, accounting for approximately 13% of the sphingosine in human skin. It can be phosphorylated by sphingosine kinases to produce C-17 sphingosine-1-phosphate. More commonly, sphingosine C-17 is used as an internal standard in the analysis of sphingoid compounds by chromatographic or spectrometric methods.

Uses

D-erythro-Sphingosine-C17 is a substrate for sphingosine kinase.

Uses

Sphingosine (d17:1) has been used as a lipid standard in the analysis of sphingolipids by liquid chromatography-mass spectrometry (LC-MS) and tandem mass spectrometry.

Definition

ChEBI: C17 sphingosine is a sphingoid that is the C17 analogue of sphingosine. It is an aminodiol and a sphingoid. It is a conjugate base of a C17 sphingosine(1+).

General Description

Sphingosine (d17:1) or D-erythro-sphingosine is a 17-carbon sphingolipid, found in human skin. It has one carbon less than naturally occurring C18-sphingosine.

Biochem/physiol Actions

Sphingosine acts a precursor for sphingosine-1-phosphate (S1P). Sphingosine C-17 is used as an internal standard in the analysis of sphingolipids by spectrometric methods.

References

[1] MARY ELLEN STEWART Donald T D. Free Sphingosines of Human Skin Include 6-Hydroxysphingosine and Unusually Long-Chain Dihydrosphingosines[J]. Journal of Investigative Dermatology, 1995, 105 4: Pages 613-618. DOI: 10.1111/1523-1747.ep12323736
[2] JEONG HEE HONG . K6PC-5, a Direct Activator of Sphingosine Kinase 1, Promotes Epidermal Differentiation Through Intracellular Ca2+ Signaling[J]. Journal of Investigative Dermatology, 2008, 128 9: Pages 2166-2178. DOI: 10.1038/jid.2008.66
[3] CHANG-HWAN CHOI. Sphingosine 1-Phosphate and Sphingosine Kinase Activity during Chicken Embryonic Development[J]. Archives of Pharmacal Research, 2007, 30 4: 502-506. DOI: 10.1007/bf02980226
[4] STEVEN W PAUGH. A selective sphingosine kinase 1 inhibitor integrates multiple molecular therapeutic targets in human leukemia.[J]. Blood, 2008: 1382-1391. DOI: 10.1182/blood-2008-02-138958
[5] KAZUAKI TAKABE. Estradiol induces export of sphingosine 1-phosphate from breast cancer cells via ABCC1 and ABCG2.[J]. The Journal of Biological Chemistry, 2010: 10477-10486. DOI: 10.1074/jbc.m109.064162

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