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Steroid


DATA No : SST0122 INFORMANT : Hideaki Nishino

NAME : 2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene

COMMON NAME: Squalene / Spinacene / Supraene
SYMBOL:
FORMULA: C30H50 MOL.WT (average) : 410.718


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BIOLOGICAL ACTIVITY
Synthesis using geraniol. (Ref. 0553) Stereoisomer-specific synthesis. (all-trans-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene). (Ref. 0554/0556) Synthesis from 2-farnesylthiothiazoline. (Ref. 0557) Application of general synthetic method of 1,5-diene. (Ref. 0558) Synthesis of trans-cis-trans-trans isomer, and preparation of tritium-labeled squalene. (Ref. 0559)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:about -75deg (Ref. 0547)

BOILING POINT:bp/25=285deg, bp/2=240deg, bp/0.15=203deg (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
Shark liver oil. (Ref. 0547) Centrophorus granulosus, Spinax niger, Scymnorhinus lichia. (Ref. 0548)
CHEMICAL SYNTHESIS
Intermediate in cholesterol biosynthesis. (Ref. 0554)
METABOLISM
Sterilizer. (Ref. 0547)
GENETIC INFORMATION

NOTE
Somewhat stinks in oily state. (Ref. 0547) 12cps.viscosity at 25degC. (Ref. 0547) The flashing point, about 200degC. (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
[0547]
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)
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[0548]
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)
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[0551]
AUTHOR:Karrer,P.,and Helfenstein,A.
TITLE:Synthese des Squalens.
JOURNAL:Helv. Chim. Acta
VOL:14 PAGE : 78 -84 (1931)
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[0552]
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)
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[0553]
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)
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[0554]
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)
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[0555]
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)
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[0556]
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)
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[0557]
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)
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[0558]
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)
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[0559]
AUTHOR:Biellmann,J.F.,and Ducep,J.B.
TITLE:Synthèse du squalène et d'analogues.
JOURNAL:Tetrahedron
VOL:27 PAGE : 5861 -5872 (1971)
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