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Steroid


DATA No : SST0012 INFORMANT : Hideaki Nishino

NAME : Ergosta-5,7,22-trien-3b-ol

COMMON NAME: Ergosterol / Ergosterin / Provitamin D2
SYMBOL:
FORMULA: C28H44O1 MOL.WT (average) : 396.648


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BIOLOGICAL ACTIVITY
Antirachitic activity as 1,25-dihydroxyergocalciferol. (Ref. 0102)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:168degC (alcohol) (Ref. 0098)

BOILING POINT:bp0.01 = 250degC (Ref. 0098)

REFRACTIVE INDEX:

OPTICAL ROTATION:[a] 20/D=-135deg (c=1.2 in chloroform), [a] 20/546=-171deg(chloroform) (Ref. 0099)

DENSITY:

SOLUBILITY:Sol in heated chloroform, benzene. Slightly sol in methanol, ethanol, ether, petroleum ether. Insol in water. (Ref. 0050)
SPECTRAL DATA
UV SPECTRA:max. nm (e); 262 (6,940); 271 (10,000); 282 (10,600); 293 (6,060). min. nm (e); 230 (1,430); 263 (6,850); 275.5 (8,580); 289 (5,450); 317.5 (35) (Ref. 0008)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:E 1%/1cm: nm(e); 36.1 (2,300); 175 (2,620); 173 (2,630); 253 (2,710); 217 (2,755); 268 (2,820); 138 (2,890); 158 (2,930); 0.8 (3,175) (Ref. 0046)
CHROMATOGRAM DATA

SOURCE
Ergots, yeasts, Chlorella, molds. (Ref. 0100/0101) Trypanosoma, soil amoeba, Lycopodium complanatum. (Ref. 0102)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
Precipitable by digitonin. Positive in Rosenheim reaction. (Ref. 0097)
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]

[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]

[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]

[0097]
AUTHOR:Chung,C.K.
TITLE:Über die Konstitution des Ergosterins.
JOURNAL:Justus Liebigs Ann Chem.
VOL:500 PAGE : 270 -280 (1933)
[TOP]

[0098]
AUTHOR:Bills,C.E., and Honeywell,E.M.
TITLE:Antiricketic Substances. VIII. Studies on Highly Purified Ergosteroles and Its Esters.
JOURNAL:J.Biol.Chem.
VOL:80 PAGE : 15 -23 (1928)
[TOP]

[0099]
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), pp574-574, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0100]
AUTHOR:Bills,C.E.
TITLE:Physiology of the Sterols, Including Vitamin D.
JOURNAL:Physiol.Rev.
VOL:15 PAGE : 1 -97 (1935)
[TOP]

[0101]
AUTHOR:Tanret,C.
TITLE:Ergosterol and Fongisterol.
JOURNAL:Ann.Chim.Phys.
VOL:15 PAGE : 313 -330 (1908)
[TOP]

[0102]
AUTHOR:Bekemeier, H., and Benad, A.
TITLE:[On the annual rhythm of the efficacy of antirachitic and toxic doses of vitamin D] PubMed ID:5321600
JOURNAL:Int Z Vitaminforsch.
VOL:35 PAGE : 247-257 (1965)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.