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	:	149-150C (Ref. 0043)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	[a]20/D=-122.5(benzene), -113.6(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)

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[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)

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[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)

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[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 : - ()

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[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)

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[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 : - ()

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[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)

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[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)

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[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)

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[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)

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[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)

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[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)

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[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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