|
| COMMON NAME | : | Squalene / Spinacene / Supraene |
| SYMBOL | : | |
| FORMULA | : | C30H50 MOL.WT (average) : 410.718 |
| BIOLOGICAL ACTIVITY |
| PHYSICAL AND CHEMICAL PROPERTIES |
| MELTING POINT | : | about -75 (Ref. 0547) |
| BOILING POINT | : | bp/25=285, bp/2=240, bp/0.15=203 (Ref. 0547) |
| REFRACTIVE INDEX | : | |
| OPTICAL ROTATION | : | n20/D=1.4965 (Ref. 0547) |
| DENSITY | : | |
| SOLUBILITY | : | Insol in water. Sol in ether, petroleum ether, carbon tetrachloride, acetone. Sparingly sol in glacial acetic acid, alcohol. (Ref. 0547) |
| SPECTRAL DATA |
| UV SPECTRA | : | |
| IR SPECTRA | : | Comparison between natural and synthetic compounds. Identification of characteristic peaks at around 9-11m,12m (Ref. 0553) |
| NMR SPECTRA | : | |
| MASS SPECTRA | : | |
| OTHER SPECTRA | : | Molar refraction 139.6, 139.8, 139.9 (Ref. 0547) |
| CHROMATOGRAM DATA |
| SOURCE |
| CHEMICAL SYNTHESIS |
| METABOLISM |
| GENETIC INFORMATION |
| NOTE |
C. (Ref. 0547) The flashing point, about 200C. (Ref. 0547) Intermediate for synthesis of drugs. (Ref. 0547) Intermediate for organic pigments, synthetic rubber, aroma, surfactants. (Ref. 0551/0552) Iodine value 377.6 (Ref. 0547) Occupied 50-80% of liver oil. (Ref. 0547) Crystal structure (Ref. 0555) | REFERENCES |
| AUTHOR | : | Heilbron,I.M.,Kamm,E.D.,and Owens,W.M. |
| TITLE | : | The unsaponifiable matter from the oils of Elasmobranch fish. Part I. A contribution to the study of the constitution of squalene (spinacene). |
| JOURNAL | : | J. Chem. Soc. |
| VOL | : | 1926 PAGE : 1630 -1644 (1926) |
| AUTHOR | : | Heilbron,I.M.,Owens,W.M.,and Simpson,I.A. |
| TITLE | : | The unsaponifiable matter from the oils of Elasmobranch fish. Part V. The constitution of squalene as deduced from its degradation products. |
| JOURNAL | : | J. Chem. Soc. |
| VOL | : | 1929 PAGE : 873 -883 (1929) |
| AUTHOR | : | Karrer,P.,and Helfenstein,A. |
| TITLE | : | Synthese des Squalens. |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 14 PAGE : 78 -84 (1931) |
| AUTHOR | : | Karrer,P.,Helfenstein,A.,Pieper,B.,and Wettstein,A. |
| TITLE | : | Pflanzenfarbstoffe XXIX. Die Symmetrische Lycopinformel. Perhydro-lycopin. |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 14 PAGE : 435 -438 (1931) |
| AUTHOR | : | Dicker,D.W.,and Whiting,M.C. |
| TITLE | : | Synthetical studies on terpenoids. Part I. The Synthesis of Squalene. |
| JOURNAL | : | J. Chem. Soc. |
| VOL | : | 1958 PAGE : 1994 -2000 (1958) |
| AUTHOR | : | Cornforth,J.W.,Cornforth,R.H.,and Mathew,K.K. |
| TITLE | : | A stereoselective synthesis of squalene. |
| JOURNAL | : | J. Chem. Soc. |
| VOL | : | 1959 PAGE : 2539 -2547 (1959) |
| AUTHOR | : | Ernst,J.,Sheldrick,W.S.,and Fuhrhop,J.-H. |
| TITLE | : | The crystal structure of squalene. |
| JOURNAL | : | Angew. Chem. Int. Ed. |
| VOL | : | 15 PAGE : 778 -778 (1976) |
| AUTHOR | : | Johnson,W.S.,Werthemann,L.,Bartlett,W.R.,Brocksom,T.J.,Li,T.-T.,Faulkner,D.J.,and Petersen,M.R. |
| TITLE | : | A simple stereoselective version of the claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 92 PAGE : 741 -743 (1970) |
| AUTHOR | : | Hirai,K.,Matsuda,H.,And Kishida,Y. |
| TITLE | : | A new synthesis of squalene using 2-alkenylthio-thiazolinelithium derivatives. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 1971 PAGE : 4359 -4362 (1971) |
| AUTHOR | : | Grieco,P.A.,and Masaki,Y. |
| TITLE | : | A general 1,5-diene synthesis. Application to the synthesis of squalene. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 39 PAGE : 2135 -2136 (1974) |
| AUTHOR | : | Biellmann,J.F.,and Ducep,J.B. |
| TITLE | : | Synthèse du squalène et d'analogues. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 27 PAGE : 5861 -5872 (1971) |