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D-erythro-C20-Dihydrosphingosine

Product NameD-erythro-C20-Dihydrosphingosine
CAS24006-62-0
MFC20H43NO2
MW329.56
EINECS
MOL File24006-62-0.mol

Chemical Properties

Boiling point	471.9±25.0 °C(Predicted)
Density	0.920±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	Chloroform:Methanol (5:1): soluble; Ethanol: soluble, warmed
form	A solid
pka	12.57±0.45(Predicted)
InChI	1S/C20H43NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(21)18-22/h19-20,22-23H,2-18,21H2,1H3/t19-,20+/m0/s1
InChIKey	UFMHYBVQZSPWSS-VQTJNVASSA-N
SMILES	OC[C@@](N)([H])[C@]([H])(O)CCCCCCCCCCCCCCCCC

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Sphinganine (d20:0) is a natural isomer of dihydro-D-erythro-sphinganine (sphinganine (d18:0); ) that is a precursor of ceramide and sphingosine as well as a substrate for sphingosine kinases, which generate sphingosine-1-phosphate (d18:1) . In S. cerevisiae, the amount of sphinganine (d20:0) increases 10.8-fold in response to heat stress, indicating it is involved in heat stress adaptation. Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins as well as in some cancers. Sphinganine can block protein kinase C activation in some cases but not others. [Matreya, LLC. Catalog No. 1845]

Uses

Sphinganine-C20 is a sphingolipid that plays an important role in the regulation of central cellular processes, including cell growth, survival and differentiation.

Definition

ChEBI: A 2-aminoicosane-1,3-diol having (2S,3R)-configuration.

References

[1] G M JENKINS. Involvement of yeast sphingolipids in the heat stress response of Saccharomyces cerevisiae.[J]. The Journal of Biological Chemistry, 1997, 272 51: 32566-32572. DOI: 10.1074/jbc.272.51.32566
[2] JUN YIN . Altered sphingolipid metabolism induced by tumor hypoxia – New vistas in glycolipid tumor markers[J]. FEBS Letters, 2010, 584 9: Pages 1872-1878. DOI: 10.1016/j.febslet.2009.11.019
[3] SARAH T PRUETT. Biodiversity of sphingoid bases (“sphingosines”) and related amino alcohols.[J]. Journal of Lipid Research, 2008, 49 8: 1621-1639. DOI: 10.1194/jlr.r800012-jlr200
[4] G S SHEPHARD V S L Van Der Westhuizen. Biomarkers of exposure to fumonisin mycotoxins: a review.[J]. Food additives and contaminants, 2007, 24 10: 1196-1201. DOI: 10.1080/02652030701513818
[5] A. MERRILL. Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases.[J]. The Journal of Biological Chemistry, 1986, 1 1: 12610-12615. DOI: 10.1016/s0021-9258(18)67134-0
[6] JR. A H M. Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds[J]. Biochemistry Biochemistry, 1989, 28 8: 3138-3145. DOI: 10.1021/bi00434a004

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