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Steroid


DATA No : SST0007 INFORMANT : Hideaki Nishino

NAME : Cholesta-5,7-dien-3b-ol

COMMON NAME: 7-Dehydrocholesterol / Provitamin D3
SYMBOL: 7-DHC
FORMULA: C27H44O1 MOL.WT (average) : 384.638


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BIOLOGICAL ACTIVITY
Immediate precursor to cholesterol. (Ref. 0051/0052)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:149-150degC (Ref. 0043)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]20/D=-122.5deg(benzene), -113.6deg(chloroform) (Ref. 0043/0045)

DENSITY:

SOLUBILITY:Sol in ether, chloroform. Slightly sol in methanol. Insol in water (Ref. 0045)
SPECTRAL DATA
UV SPECTRA:nm(e): min. 230 (150), max. 262.5 (740), max. 271 (1,040), min. 276 (883), max. 281.5 (1,075), min. 288 (553), max. 293 (615), max. 321 (36). (Ref. 0008)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:E1%/1cm (l, nm): 39.1 (2,300), 193 (2,625), 271 (2,710), 230 (2,760), 280 (2,815), 144 (2,880), 160 (2,930), 0.9 (3,210). (Ref. 0046)
CHROMATOGRAM DATA

SOURCE
Tissues of animals (Ref. 0047) , pig derma (5 % of total sterols) (Ref. 0048) , Horned snail (Buccinum undatum). (Ref. 0049/0050)
Antirachitic activity as vitamin D3 after conversion to cholecalcipherol by ultraviolet irradiation and hydroxylation. (Ref. 0051/0052)
CHEMICAL SYNTHESIS
Synthesis from cholesterol via 7-bromocholesteryl ester. (Ref. 0053/0054)
METABOLISM

GENETIC INFORMATION
Possibly excess accumulation relates to holoprosencephalic disorder. (Ref. 0055)
NOTE
Precipitable by digitonin. (Ref. 0042)
REFERENCES
[0008]
AUTHOR:Hogness,T.R., Sidwell,Jr.,A.R., and Zscheile,Jr.,F.P.
TITLE:The Absorption Spectra of Compounds Related to the Sterols
JOURNAL:J.Biol.Chem.
VOL:120 PAGE : 239 -256 (1937)
[TOP]

[0042]
AUTHOR:Windaus,A., Lettre,H., and Schenck,Fr.
TITLE:Über das 7-Dehydro-Cholesterin
JOURNAL:Justus Liebigs Ann Chem.
VOL:520 PAGE : 98 -106 (1935)
[TOP]

[0043]
AUTHOR:Boer,A.G., Reerink,E.H., van Wijk,A., and van Niekerk,J.
TITLE:A Naturally Occurring Chicken Provitamin-D.
JOURNAL:Proc.Acad.Sci.Amsterdam
VOL:39 PAGE : 622 -632 (1936)
[TOP]

[0045]
AUTHOR:Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp2857-2858, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0046]
AUTHOR:Loofbourow,J.R.
TITLE:Physical Methods for Identification and Assay of Vitamins and Hormones.
JOURNAL:Vitamins and Hormones
VOL:1 PAGE : 109 -155 (1943)
[TOP]

[0047]
AUTHOR:Deuel,Jr.,H.T.(1951) Distribution, Properties, and Chemistry of the Provitamins D and Vitamins D in the Lipids Their Chemistry and Biochemistry I (Deuel,Jr.,H.J., eds.), pp739-792, Interscience Publishers, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0048]
AUTHOR:Windaus,A., and Bock,F.
TITLE:Über das Provitamin aus dem Sterin der Schweinschwarte.
JOURNAL:Z.Physiol.Chem.
VOL:245 PAGE : 168 -170 (1937)
[TOP]

[0049]
AUTHOR:Bock,F., and Wetter,F.
TITLE:Über die bei Einigen Avertebraten Vorkommenden Antirachitishen Provitamine
JOURNAL:Z.Physiol.Chem.
VOL:256 PAGE : 33 -41 (1938)
[TOP]

[0050]
AUTHOR:Windaus,A.
TITLE:The Antirachitic Provitamins in the Animal Kingdom
JOURNAL:Nachr.Ges.Wiss.Göttingen, Math.-Physk.Klasse, Fachgruppe III
VOL:1 PAGE : 185 -192 (1936)
[TOP]

[0051]
AUTHOR:Windaus,A., Schenck,Fr., and von Werder,F.
TITLE:Über das Antirachitisch Wirksame Bestrahlungsprodukt aus 7-Dehydro-Cholesterin.
JOURNAL:Z.Physiol.Chem.
VOL:241 PAGE : 100 -103 (1936)
[TOP]

[0052]
AUTHOR:Windaus,A., Deppe,N., and Wunderlich,W.
TITLE:Über Einige Bestrahlungsprodukte aus 7-Dehydro-Cholesterin.
JOURNAL:Justus Liebigs Ann Chem.
VOL:533 PAGE : 118 -127 (1938)
[TOP]

[0053]
AUTHOR:Buisman,J.A.K., Stevens,W., and von der Vliet,J.
TITLE:Investigations on Sterols. I. A New Synthesis of 7-Dehydrocholesterol (Provitamin D).
JOURNAL:Rec.Trav.Chim.
VOL:66 PAGE : 83 -92 (1947)
[TOP]

[0054]
AUTHOR:Confalone,P.N., Kulesha,I.D., and Uskokovic,M.R.
TITLE:A New Synthesis of 7-Dehydrocholesterols.
JOURNAL:J.Org.Chem.
VOL:46 PAGE : 1030 -1032 (1981)
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[0055]
AUTHOR:Salen, G., Shefer, S., Batta, A. K., Tint, G. S., Xu, G., Honda, A., Irons, M., and Elias, E. R.
TITLE:Abnormal cholesterol biosynthesis in the Smith-Lemli-Opitz syndrome PubMed ID:8808751
JOURNAL:J Lipid Res.
VOL:37 PAGE : 1169-1180 (1996)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.