Long chain base and Ceramide

DATA No : DLB0010 INFORMANT : Akira Hayashi

NAME : D(+)-Sphinganine/D(+)- Erythro-1,3-dihydroxy-2-aminooctadecane/D(+)-2S, 3R-1, 3-dihydroxy-2-aminooctadecane

COMMON NAME	:
SYMBOL	:	d18:0
FORMULA	:	C₁₈H₃₉O₂N₁ MOL.WT (average) : 301.508

Download ChemDraw structure data

BIOLOGICAL ACTIVITY

Effect on phorbol-dependent differentiation of HL-60 cell(Ref. 0037)

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:	143-145C(tribenzoyldihydrosphingosine) (Ref. 0034)/122-123 C/79C (Ref. 0261)/124-125C (N-acetyl-D(+)-sphinganine) (Ref. 0261)/ 96-97C (Triacetyl deriv.) (Ref. 0261)

BOILING POINT	:

REFRACTIVE INDEX	:	[a]²²_D=+19.2 (Erythro-triacetyl) (Ref. 0023)

OPTICAL ROTATION	:	[a]²⁸₅₄₆ = +6.0 (in CHCl3-MeOH, 10:1) (Ref. 0261)/[a]²⁸₅₄₆ = +7.7 (in Hexeane-EtOH, 10:1) (N-acetyl deriv.) (Ref. 0261) [a]²⁸₅₄₆ =+21 in hexane-EtOH(10:1) (Triacetyl deriv.) (Ref. 0261)

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:	Racem. Threo-triacetyl-dihydrosphingosine (Ref. 0024)/Optically active triacetyldihydrosphingosine (Ref. 0024)/Raswm. Erythro-triacetyl-dihydrosphingosine(Ref. 0024)

NMR SPECTRA	:	¹H-NMR (Ref. 0260)

MASS SPECTRA	:	EI-MS of N-acetyl-O-TMS-LCB shows no molecular ion, but shows [M-15 ] ion (m/z 472) and [M-103] ion. (Ref. 0025)

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Ceramide phospholipid obtained from CR2A strain of anaerobic bacteria, Bacteroides melaninogenicus (Ref. 0025)/Milk sphingomyelin (5.9 mole %) (Ref. 0016)

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

GC data (column: 2% OV-1) of N-Acetyl-O-TMS-LCB (Ref. 0025)

REFERENCES

[0016]

AUTHOR	:	Morrison, W. R.
TITLE	:	Polar lipids in bovine milk. I. Long-chain bases in sphingomyelin PubMed ID:5816447
JOURNAL	:	Biochim Biophys Acta.
VOL	:	176 PAGE : 537-546 (1969)

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[0023]

AUTHOR	:	Carter, H.E. and Shapiro, D.
TITLE	:	Configuration of dihydrosphingosine.
JOURNAL	:	J. Amer. Chem. Soc.
VOL	:	75 PAGE : 5131 -5132 (1953)

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[0024]

AUTHOR	:	Jenny, E.F. and Grob, C.A.
TITLE	:	Die Synthese von Erythro-Dihydrosphingosin aus Trans-2-Octadecene-1-asure
JOURNAL	:	Helv. Chim. Acta
VOL	:	36 PAGE : 1936 -1944 (1953)

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[0025]

AUTHOR	:	White, D. C., Tucker, A. N., and Sweeley, C. C.
TITLE	:	Characterization of the iso-branched sphinganines from the ceramide phospholipids of Bacteroides melaninogenicus PubMed ID:5364262
JOURNAL	:	Biochim Biophys Acta.
VOL	:	187 PAGE : 527-532 (1969)

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[0034]

AUTHOR	:	Carter, H.E., Glick, F.J., Norris, W.P., and Phillips, G.E.
TITLE	:	Biochemistry of the sphingosine III. Structure of sphingosine
JOURNAL	:	J. Biol. Chem.
VOL	:	170 PAGE : 285 -294 (1947)

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[0037]

AUTHOR	:	Merrill, A. H., Jr., Sereni, A. M., Stevens, V. L., Hannun, Y. A., Bell, R. M., and Kinkade, J. M., Jr.
TITLE	:	Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases PubMed ID:3462189
JOURNAL	:	J Biol Chem.
VOL	:	261 PAGE : 12610-12615 (1986)

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[0260]

AUTHOR	:	Ando, S.
TITLE	:	Recent progress in the structural stdies of glycolipids (in Japanese)
JOURNAL	:	J. Jpn. Oil Chem. Soc.
VOL	:	21 PAGE : 243 -256 (1972)

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[0261]

AUTHOR	:	Stoffel, W.
TITLE	:	Chemistry and biochemistry of sphingosine bases PubMed ID:4772653
JOURNAL	:	Chem Phys Lipids.
VOL	:	11 PAGE : 318-334 (1973)

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