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Ergosterol CAS Registry Number: 57-87-4 麦角固醇; 麦角甾醇


CAS Name: (3b,22E)-Ergosta-5,7,22-trien-3-ol
Additional Names: ergosta-5:6,7:8,22:23-trien-3-ol; ergosterin
Percent Composition: C 84.78%, H 11.18%, O 4.03%
📌 参考资料/链接:
Literature References: Most important of the provitamins D. Usually obtained from yeast which synthesizes it from simple sugars such as glucose. Damp yeast yields about 2.5% ergosterol, the variety of the yeast being very important. Isoln procedure: Green et al., US 3006932 (1961 to Vitamins Ltd.). When irradiated with uv light, ergosterol develops powerful vitamin D2, q.v., activity. Askew et al., in England and Windaus and collaborators in Germany isolated the antirachitic vitamin D2. The main irradiation products of ergsterol are lumisterol®tachysterol®vitamin D2. Structure: Chuang, Ann. 500, 270 (1933). Oxidation products: Fuerst, Arch. Pharm. 300, 144 (1967).

📄 详细内容


Properties: Small hydrated plates from alcohol, in hydrated needles from ether. The best crystallized form contains 1½ mol H2O, mp 168°: Bills, Honeywell, J. Biol. Chem.
80, 15 (1928). Complete removal of water is almost impossible and results in an amorphous mass, melting range 166-183°. bp0.01 250°. [a]D20 -135° (c = 1.2 in CHCl3 calcd as anhydr). [a]20546 -171° (CHCl3). uv max (ethanol): 262, 271, 282, 293 nm, Hogness et al., ibid.
120, 239 (1937). Practically insol in water. One gram dissolves in 660 ml alcohol, in 45 ml boiling alcohol, in 70 ml ether, in 39 ml boiling ether, in 31 ml chloroform. Precipitated by digitonin. Affected by light and air, turns yellow. Oxygen forms peroxides and hydrogen may form polyhydro compds.
Melting point: mp 168°: Bills, Honeywell, J. Biol. Chem.
80, 15 (1928)
Boiling point: bp0.01 250°
Optical Rotation: [a]D20 -135° (c = 1.2 in CHCl3 calcd as anhydr); [a]20546 -171° (CHCl3)
Absorption maximum: uv max (ethanol): 262, 271, 282, 293 nm, Hogness et al., ibid.
120, 239 (1937)
Derivative Type: Acetate
Percent Composition: C 82.14%, H 10.57%, O 7.29%
Properties: mp 179°, clear at 181°.
Melting point: mp 179°
Derivative Type: Benzoate
Percent Composition: C 83.95%, H 9.66%, O 6.39%
Properties: Plates or needles, mp 169-171°. [a]D23 -71° (c = 1.1 in CHCl3), [a]546 -88° (CHCl3).
Melting point: mp 169-171°
Optical Rotation: [a]D23 -71° (c = 1.1 in CHCl3); [a]546 -88° (CHCl3)
Derivative Type: 22,23-Dihydro analog
Additional Names: 22,23-Dihydroergosterol
Percent Composition: C 84.36%, H 11.63%, O 4.01%
Literature References: Prepn: A. Windhaus, R. Langer, Ann.
508, 105 (1934); D. H. R. Barton et al., J. Chem. Soc. Perkin Trans. 1
1976, 821; D. J. Curry et al., ibid.
1977, 822. uv irradiation gives vitamin D4, q.v.
Properties: Solvated needles from ethyl acetate + methanol, mp 152-153° (dried). [a]D19 -109° (CHCl3) (Windhaus); also reported as needles from chloroform-methanol, mp 128-130°. [a]D19 -121° (c = 0.1). uv max: 262, 272, 282, 294 nm (e 8000, 11200, 11800, 6800) (Barton).
Melting point: mp 152-153° (dried); mp 128-130°
Optical Rotation: [a]D19 -109° (CHCl3) (Windhaus); [a]D19 -121° (c = 0.1)
Absorption maximum: uv max: 262, 272, 282, 294 nm (e 8000, 11200, 11800, 6800) (Barton)
Derivative Type: 22,23-Dihydro analog acetate
Percent Composition: C 81.76%, H 10.98%, O 7.26%
Properties: mp 157-158°. [a]D17 -75° (c = 2.1 in CHCl3).
Melting point: mp 157-158°
Optical Rotation: [a]D17 -75° (c = 2.1 in CHCl3)
Therap-Cat: Vitamin (antirachitic).
Keywords: Vitamin/Vitamin Source; Vitamin D.
产品链接: 57-87-4››