Sphingosine
Title: Sphingosine
CAS Registry Number: 123-78-4
CAS Name: (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol
Additional Names: (E)-D-erythro-4-octadecene-1,3-diol; 1,3-dihydroxy-2-amino-4-octadecene; 4-sphingenine
Molecular Formula: C18H37NO2
Molecular Weight: 299.49
Percent Composition: C 72.19%, H 12.45%, N 4.68%, O 10.68%
Literature References: Important membrane component; long-chain amino-dialcohol; moiety of certain phosphatides, such as sphingomyelins, cerebrosides, and gangliosides. Natural sphingosine is D-(+)-erythro-1,3-dihydroxy-2-amino-4-trans-octadecene. Does not exist in the free state in animals, plants or microorganisms. First obtained by hydrolysis of cerebrosides from brains: J. L. W. Thudichum, Die Konstitution des Gehirns des Menschen und der Tiere (Tübingen, 1901). Separation procedures: Carter et al., J. Biol. Chem. 170, 269 (1947); Wittenberg, ibid. 216, 379 (1955); Tipton, Biochem. Prep. 9, 127 (1962). Stereospecific synthesis of DL-erythro-trans-form and isomers: C. A. Grob, F. Gadient, Helv. Chim. Acta 40, 1145 (1957). Stereoselective synthesis: H. Newman, J. Am. Chem. Soc. 95, 4098 (1973); B. Bernet, A. Vasella, Tetrahedron Lett. 24, 5491 (1983). Comprehensive review: C. A. Grob, Record Chem. Progr. (Kresge-Hooker Sci. Lib.) 18, 55-66 (1957); D. Shapiro, Chemistry of Sphingolipids (Hermann, Paris, 1969) 111 pp. Bibliography: Rodd's Chemistry of Carbon Compounds Vol. I, part E, S. Coffey, Ed. (Elsevier, New York, 2nd ed., 1976) pp 394-397.
 
Derivative Type: DL-Sphingosine
Properties: Waxy crystals from ether + pentane, mp 67°.
Melting point: mp 67°
 
Derivative Type: DL-Triacetylsphingosine
Molecular Formula: C24H43NO5
Molecular Weight: 425.60
Percent Composition: C 67.73%, H 10.18%, N 3.29%, O 18.80%
Properties: Crystals from pentane + ether, mp 91-92°.
Melting point: mp 91-92°
 
Derivative Type: Triacetyl derivative of natural sphingosine
Molecular Formula: C24H43NO5
Molecular Weight: 425.60
Percent Composition: C 67.73%, H 10.18%, N 3.29%, O 18.80%
Properties: Crystals, mp 101-102°. [a]D25 -11.7° (chloroform).
Melting point: mp 101-102°
Optical Rotation: [a]D25 -11.7° (chloroform)

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