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

BOILING POINT:

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

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

[0023]
AUTHOR:Carter, H.E. and Shapiro, D.
TITLE:Configuration of dihydrosphingosine.
JOURNAL:J. Amer. Chem. Soc.
VOL:75 PAGE : 5131 -5132 (1953)
[TOP]

[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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[0261]
AUTHOR:Stoffel, W.
TITLE:Chemistry and biochemistry of sphingosine bases PubMed ID:4772653
JOURNAL:Chem Phys Lipids.
VOL:11 PAGE : 318-334 (1973)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.