| Identification | Back Directory | [Name]
(2S,3R,E)-2-Amino-4-heptadecene-1,3-diol | [CAS]
6918-48-5 | [Synonyms]
C17-Sphingosine
Sphingosine (d17:1)
C17-D-erythro-Sphingosine
D-erythro-Sphingosine C-17
D-erythro-sphingosine (C17 base)
D-erythro-Heptadecasphing-4-enine
(2S,3R,E)-2-Amino-4-heptadecene-1,3-diol
D-ERYTHRO-SPHINGOSINE (C17 BASE);SPHINGOSINE (D17:1) | [Molecular Formula]
C17H35NO2 | [MDL Number]
MFCD18427933 | [MOL File]
6918-48-5.mol | [Molecular Weight]
285.47 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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