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Steroid


DATA No : SST0081 INFORMANT : Hideaki Nishino

NAME : Cholest-5-ene-3,25-diol / D5-Cholestene-3b,25-diol

COMMON NAME: 25-Hydroxycholesterol
SYMBOL:
FORMULA: C27H46O2 MOL.WT (average) : 402.653


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BIOLOGICAL ACTIVITY
Preparation by treatment of 3b-acetoxy-5-cholestene-25-one with methylmagnesium. (Ref. 0425/0426) Not product of biogenesis, but oxidation of cholesterol in the air. (Ref. 0422) Efficient and simple synthesis. Regioselective protocol without forming 24-hydroxyisomer. (Ref. 0433) Synthesis of 25-hydroxycholesteryl 3b-acetate by UV-irradiation of 3b-acetoxycholestane. (Ref. 0434) Generally available synthesis method from pregnenolone and the acetate (Ref. 0428) Synthesis from 2-lithiodithian (Ref. 0428)Synthesis from stigmasterol (Ref. 0432) Synthesis from 5b-cholestan-3a,25-diol derived from lithocholic acid. (Ref. 0435) Synthesis by using (h3-allyl)palladium. (Ref. 0429)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:178-180degC (Ref. 0425/0426)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]25/D=-39.0deg (c=1.05 in chloroform) (Ref. 0425/0426)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:(CHCl3) 3620(OH), 1050, 1020, 960, 930, 910/cm (Ref. 0427/0428)

NMR SPECTRA:(CDCl3) d 5.33(m, H-6); 3.48(m, -CH-O); 1.19(s,H3C-C(26) and H3C-C(27)); 1.00(s,H3C-C(19)); 0.92(d,J=7Hz,CH3); 0.67(s,H3C-C(18)).

MASS SPECTRA:Molecular ion m/e 402 (Ref. 0427/0428/0429)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Contamination as a trace component in cholesterol preparation. (Ref. 0422)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
Useful for synthesis of vitamin D3 intermediates, 25-hydroxycholecalciferol and 1,25-dihydroxycholecalciferol (Ref. 0427/0428/0430/0431/0432)
REFERENCES
[0422]
AUTHOR:Fieser,L.F.,Huang,W.-Y.,and Bhattacharyya,B.K.
TITLE:Cholesterol and companions. X. The diol fraction.
JOURNAL:J. Org. Chem.
VOL:22 PAGE : 1380 -1384 (1957)
[TOP]

[0425]
AUTHOR:Ryer,A.I.,Gebert,W.H.,and Murrill,N.M.
TITLE:The preparation of cholesterol from 25-ketonorcholesterol.
JOURNAL:J. Am. Chem. Soc.
VOL:72 PAGE : 4247 -4248 (1950)
[TOP]

[0426]
AUTHOR:Dauben,W.G.,and Bradlow,H.L.
TITLE:The preparation of cholesterol from D5-norcholestene-3b-ol-25-one.
JOURNAL:J. Am. Chem. Soc.
VOL:72 PAGE : 4248 -4250 (1950)
[TOP]

[0427]
AUTHOR:Partridge, J. J., Faber, S., and Uskokovic, M. R.
TITLE:Vitamin D3 metabolites. I. Synthesis of 25-hydroxycholesterol PubMed ID:4364576
JOURNAL:Helv Chim Acta.
VOL:57 PAGE : 764-771 (1974)
[TOP]

[0428]
AUTHOR:Narwid, T. A., Cooney, K. E., and Uskokovic, M. R.
TITLE:Vitamin D3 metabolites. II. Further syntheses of 25-hydroxycholesterol PubMed ID:4364577
JOURNAL:Helv Chim Acta.
VOL:57 PAGE : 771-781 (1974)
[TOP]

[0429]
AUTHOR:Riediker,M.,and Schwartz,J.
TITLE:A new synthesis of 25-hydroxycholesterol.
JOURNAL:Tetrahedron Lett.
VOL:22 PAGE : 4655 -4658 (1981)
[TOP]

[0430]
AUTHOR:Salmond,W.G.,and Maisto,K.D.
TITLE:A synthesis of 25-hydroxycholesterol.
JOURNAL:Tetrahedron Lett.
VOL:1977 PAGE : 987 -988 (1977)
[TOP]

[0431]
AUTHOR:Salmond,W.G.,Sobala,M.C.,and Maisto,K.D.
TITLE:A synthesis of 25-hydroxycholesterol.
JOURNAL:Tetrahedron Lett.
VOL:14 PAGE : 1237 -1238 (1966)
[TOP]

[0432]
AUTHOR:Salmond,W.G.,and Sobala,W.C.
TITLE:An efficient synthesis of 25-hydroxycholesterol from stigmasterol.
JOURNAL:Tetrahedron Lett.
VOL:20 PAGE : 1695 -1698 (1977)
[TOP]

[0433]
AUTHOR:Morisaki,M.,Rubio-Lightbourn,J.,and Ikekawa,N.
TITLE:Synthesis of active forms of vitamin D. I. A facile synthesis of 25-hydroxycholesterol.
JOURNAL:Chem. Pham. Bull.
VOL:21 PAGE : 457 -458 (1973)
[TOP]

[0434]
AUTHOR:Rotman,A.,and Mazur,Y.
TITLE:C-25 Hydroxylation of cholesterol derivatives.
JOURNAL:Chem. Commun.
VOL:1974 PAGE : 15 -15 (1974)
[TOP]

[0435]
AUTHOR:Ochi,K.,Matsunaga,I.,Shindo,M.,and Kaneko,C.
TITLE:The convenient synthesis of 25-hydroxycholesterol.
JOURNAL:Chem. Pham. Bull.
VOL:27 PAGE : 252 -254 (1979)
[TOP]

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