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D-erythro-Sphingosine C-17

Cayman Chemical Item Number 10007902

(CAS 6918-48-5)

D-erythro-Sphingosine C-17 (CAS 6918-48-5)

See more	Mass Spectrometry (253) Ceramides/Sphingolipids (55) Lipids (167)

Description

Sphingosine is an amino alcohol most commonly characterized by an 18-carbon unsaturated hydrocarbon chain D-erythro-Sphingosine C-18 (Item No. 10007907). However, the hydrocarbon chain length of sphingosine, and the related dihydrosphingosine, can vary from 12-26 carbons in mammalian tissues.^1,2 D-erythro-Sphingosine C-17 is a naturally-occurring but uncommon form of sphingosine, accounting for approximately 13% of the sphingosine in human skin.¹ It can be phosphorylated by sphingosine kinases to produce C-17 sphingosine-1-phosphate.³ More commonly, sphingosine C-17 is used as an internal standard in the analysis of sphingoid compounds by chromatographic or spectrometric methods.^4,5,6

1 Stewart, M.E., and Downing, D.T. Free sphingosines of human skin include 6-hydroxysphingosine and unusually long-chain dihydrosphingosines. J Invest Dermatol 105 613-618 (1995).

2 Pruett, S.T., Bushnev, A., Hagedorn, K., et al. Biodiversity of sphingoid bases (“sphingosines”) and related amino alcohols. J Lipid Res 49 1621-1639 (2008).

3 Hong, J.H., Youm, J., Kwon, M.J., et al. K6PC-5, a direct activator of sphingosine kinase 1, promotes epidermal differentiation through intracellular Ca2+ signaling. J Invest Dermatol 128 2166-2178 (2008).

4 Choi, C., Jeong, J., Yoo, B., et al. Sphingosine 1-phosphate and sphingosine kinase activity during chicken embryonic development. Arch Pharm Res 30(4) 502-506 (2007).

5 Paugh, S.W., Paugh, B.S., Rahmani, M., et al. A selective sphingosine kinase 1 inhibitor integrates multiple molecular therapeutic targets in human leukemia. Blood 112 1382-1391 (2008).

6 Takabe, K., Kim, R.H., Allegood, J.C., et al. Estradiol induces export of sphingosine 1-phosphate from breast cancer cells via ABCC1 and ABCG2. J Biol Chem 285(14) 10477-10486 (2010).

Formal Name	2S-amino-4E-heptadecene-1,3R-diol
CAS Number	6918-48-5
Molecular Formula	C₁₇H₃₅NO₂
Formula Weight	285.5
Formulation	A crystalline solid
Purity	≥98%
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCC

Background Reading

Paugh, S.W., Paugh, B.S., Rahmani, M., et al. A selective sphingosine kinase 1 inhibitor integrates multiple molecular therapeutic targets in human leukemia. Blood 112 1382-1391 (2008).

Stewart, M.E., and Downing, D.T. Free sphingosines of human skin include 6-hydroxysphingosine and unusually long-chain dihydrosphingosines. J Invest Dermatol 105 613-618 (1995).

Choi, C., Jeong, J., Yoo, B., et al. Sphingosine 1-phosphate and sphingosine kinase activity during chicken embryonic development. Arch Pharm Res 30(4) 502-506 (2007).

Hong, J.H., Youm, J., Kwon, M.J., et al. K6PC-5, a direct activator of sphingosine kinase 1, promotes epidermal differentiation through intracellular Ca2+ signaling. J Invest Dermatol 128 2166-2178 (2008).

Pruett, S.T., Bushnev, A., Hagedorn, K., et al. Biodiversity of sphingoid bases (“sphingosines”) and related amino alcohols. J Lipid Res 49 1621-1639 (2008).

Takabe, K., Kim, R.H., Allegood, J.C., et al. Estradiol induces export of sphingosine 1-phosphate from breast cancer cells via ABCC1 and ABCG2. J Biol Chem 285(14) 10477-10486 (2010).

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Size	Price	Quantity	Subtotal
1 mg	$20.00		$0.00
5 mg	$90.00		$0.00
10 mg	$160.00		$0.00
25 mg	$350.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-12. Prices are subject to change without notice.

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