Isolation of brassicasterol from steam deodorizer distillate of rapeseed oil: Some properties of its acetate tetrabromide and its reduction to 22,23-dihydrobrassicasterol

  title={Isolation of brassicasterol from steam deodorizer distillate of rapeseed oil: Some properties of its acetate tetrabromide and its reduction to 22,23-dihydrobrassicasterol},
  author={H. W. Hircher and F. Rosenstein},
Brassicasterol (5,22-ergostadien-3β-ol) was isolated from the steam deodorizer distillate of rapeseed oil and purified by acetylation, bromination, chromatography on 20% AgNO3/SiO2 columns and hydrolysis. Brassicasteryl and stigmasteryl (5,22-stigmastadien-3β-ol) acetates were brominated, and the yields of products and solubilities of the tetrabromides from the two steryl acetates were compared. Stigmasteryl acetate tetrabromide is less soluble than the corresponding brassicasteryl derivative… Expand
9 Citations
Reaction of ergosteryl acetate with maleic anhydride and preparation of 5,7-ergostadien-3β-ol
An improved, large scale synthesis of the ergosteryl acetate-maleic anhydride Diels-Alder adduct and its pyrolysis are described. The complex mixture obtained by reaction of the two constituents wasExpand
Lipase-Catalyzed Esterification of Triterpene Alcohols and Phytosterols with Oleic Acid
Oleic acid esters of phytosterols (PSs) and triterpene alcohols (TAs), derived from rice bran, were synthesized using lipases under mild conditions. Some lipases, especially from Candida rugosa, typeExpand
Titration of sterol double bonds with dibromopyridine sulfate
The cholesterol derivatives absorbed close to the theoretical quantity of bromine, whereas the Δ22-C24-alkylated sterols consumed 0.14 to 0.23 Br2 in excess of the calculated values, which indicates that at least one or two new double bonds are formed in these molecules during the bromination step. Expand
Purification of campesterol and preparation of 7-dehydrocampesterol, 7-campestenol and campestanol
Campesterol was isolated from a soybean sterol mixture and purified on a small scale by column chromatography and on a large scale by crystallization from acetone to 97% purity. Expand
Response ofDrosophila tocis- andtrans-22-dehydrocholesterol II. Ability of sterols other than cholesterol to overcome the toxicity of thetrans isomer
Four species ofDrosophila were tested, for two generations, for viability on media containing 13 different C27, C28 and C29 sterols with and withouttrans-22-dehydrocholesterol. Only cholesterol wasExpand
Separation of pairs of C-24 epimeric sterols by glass capillary gas liquid chromatography
The trimethylsilyl ethers of the epimeric pairs of sterols with saturated side chains and a pair with two double bonds in the side chain were completely separated from each other by GLC. Expand
Response ofDrosophila tocis- andtrans-22-dehydrocholesterol: I. A survey
Trans-22-dehydrocholesterol may be acting as a competitive inhibitor in the metabolism of phytosterols to cholesterol or ecdysone by the insects. Expand
Soapstock and deodorizer distillates from North American vegetable oils: Review on their characterization, extraction and utilization
Soapstock and deodorizer distillates are the major by-products from vegetable oil refining. They have little commercial value and are sold at a fraction of the oil cost. However, theirExpand
Investigation into sterol signalling in Arabidopsis
Correct sterol biosynthesis is not required in all root tissues for correct plant development, and the result may indicate the product of C-14 reductase has a critical role in plant development. Expand


Analysis of mixtures of stigmasterol, stigmastanol and sitosterol
Hydrogenation of stigmasterol yields mixtures of the three title sterols. Stigmasterol was clearly separated from the other two by gas liquid chromatography; a standard curve was constructed relatingExpand
Brassicasterol and 22,23-dihydrobr Jurassicasterol were obtained in an overall yield of 25% and 20%, respectively, from ergosterol via i -ergosterol. Expand
Purification of sitosterol
Sitosterol and stigmastanol are obtained from the Raney nickel catalyzed hydrogenation of stigmasterol. The sitosterol was separated from stigmastanol by silica gel column chromatography of itsExpand
NMR spectra of C-24 isomeric sterols
Abstract Cholesterol and four pairs of C-24 isomeric sterols, campesterol-22,23-dihydrobrassicasterol, α-spinasterol-chondrillasterol, stigmasterol-poriferasterol, andExpand
The Chemistry of the Steroids
In view of the comprehensive article on the sterols by Heilbron & Jones (1), of the treatment by Kendall (2) and by Kamm & Pfiffner elsewhere in this Volume of the various groups of steroid hormones,Expand
Sterol Utilization in the Hide Beetle, Dermestes vulpinus
The hypothesis was advanced that the sterols utilized by the insect as partial replacers of its normal cholesterol requirement were incorporated into its tissues unchanged and performed an essential role in the maintenance of the structural integrity of the cells. Expand
Hydrogenation of stigmasterol
Hydrogenations of stigmasterol over 5% Pd/C, 5% Ru/C, Pt, Raney Ni, Raney Co, Ni/kieselguhr, and tris(triphenylphosphine)chlororhodium catalysts and with diimide generated from hydrazineExpand
Synthesis of campesteryl acetate (24R)-24-methyl-3-beta-acetoxycholesten-5-ene) and its 24S-epimer.
Abstract A synthesis of campesteryl acetate and its 24 S epimer has been accomplished starting from the optically active 3,4-dimethylpentylmagnesium bromides and pregnenolone acetate. The two epimersExpand
Soybean unsaponifiables: Chromatographic investigation of shell drain condensate from a commercial deodorizer
The shell drain condensate from a commercial soybean oil deodorizer was analyzed for nonpolar unsaponifiable constituents by liquid-liquid partition chromatography. A procedure for obtaining largeExpand
Gas chromatographic determination of tocopherols and sterols in soya sludges and residues
A method is described for determining the individual and total sterols and tocopherols of soya sludges and residues through saponification followed by gas chromatographic analysis of the unsaponifiables. Expand