- NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL
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The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy] butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3(Calcifediol) in good yield.
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Page/Page column 18-19
(2020/11/23)
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- Stigmasteryl arachidate constituent from the straw of oryza sativa
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One compound stigmasteryl-3β-arachidate (1) was isolated and identified from the rice straw of Oryza sativa. The structure of the compound was elucidated by 1D and 2D NMR (COSY, HSQC and HMBC) spectroscopic techniques aided by ESI-MS and IR spectra. To be
- Chung, Ill-Min,Yoon, Jae-Yeon,Kim, Seung-Hyun,Ahmad, Ateeque
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p. 3018 - 3020
(2014/06/09)
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- Stigmasterol-3-O-β-D-arabinopyranosyl(1→4)-O-β-D- glucopyranoside from the roots of Limonia crenulata (Roxb.)
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The methanol soluble part of the concentrated ethanolic extract of defatted roots of Limonia crenulata (Roxb) when worked up phytochemically yielded a saponin which on various chemical reactions and spectral analysis was identified as; Stigmasterol-3-O-β- D-arabinopyranosyl (1→4)-O-β-D- glucopyranoside.
- Shrivastava, Archana,Parihar, Sangeeta,Jadhav, Raina
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p. 171 - 175
(2013/07/19)
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- New steroidal glycosides from the stem bark of Mimusops elengi
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Two new steroidal glycosides (1 and 2) have been isolated from the ethanolic extract of the stem bark of Mimusops elengi L. and characterized as stigmasta-5,22-dien-3β-ol-3β-D-glucuropyranosyl-(6'β→1'') -Dglucopyranoside (1) and β-sitosterol-3β-(3''',6'''
- Akhtar,Ali,Alam
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experimental part
p. 549 - 553
(2010/12/25)
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- PROCESS FOR RECOVERING STEROLS FROM A CRUDE SOURCE CONTAINING STEROL ESTERS
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A process of obtaining sterols suitable for human consumption from a crude wood pulping source containing sterol esters is disclosed. The sterols are obtained at high yield and purity. In particular, a process of obtaining sterols at high yield and purity from tall oil pitch (TOP) is disclosed. The sterols obtained can be esterified to sterol esters for use in dietary supplements and as additives for food and beverage products.
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Page/Page column 3
(2008/12/06)
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- Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide
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Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3β-O-acetyl group in the presence of the 6β group in 3β,6β-Di-O-acetyl-5α-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3β,5α,6β-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species.
- Wang, Shao-Min,Zhang, Yan-Bing,Liu, Hong-Min,Yu, Guo-Bin,Wang, Ke-Rang
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- Pentadecanoic acid β-D-glucoside from Clerodendrum inerme
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A new aliphatic glucoside, isolated from the hexane extract of aerial parts of Clerodendrum inerme, has been characterized as pentadecanoic acid-β-D-glucoside, on the basis of spectral data analyses and chemical studies. Stigmasterol glucoside was also isolated from the same extract for the first time from this plant species. The butanol extract afforded acacetin and apigenin.
- Pandey,Verma,Gupta
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p. 2161 - 2163
(2007/10/03)
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- Process for recovery of plant sterols from by-product of vegetable oil refining
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The process for recovery of plant sterols and tocopherols from deodorization distillates formed during chemical or physical refining of vegetable oils consists of the following steps: free fatty acids are removed from the deodorization distillate by vacuum distillation or by continuation solvent saponification, after the removal of free fatty acids, the received material is reacted with an aromatic carboxylic acid anhydride at a temperature of 50-150° C., under reduced pressure, after the treatment with anhydride, tocopherols are removed from the mixture, and crystalline free sterols are recovered from the distillation residue containing sterol esters, di- and triglycerides by transesterification.
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Page/Page column 5-6
(2008/06/13)
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- Preparation of bile acids
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Certain bile acids find use in the pharmaceutical industry. In view of the wide distribution of serious diseases such as HIV, AIDS and Bovine Spongiform Encephalopathy (BSE) it is desirable to avoid—as far as practicable—to have any components of animal origin in medicaments in order to eliminate any danger of infection. The present invention relates to a method of providing bile acids from non-animal starting materials.
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- Method of producing a vitamin product
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A process for producing a nutrient supplement powder is provided. The process forms a powder into a plastic mass which is not completely molten. The plastic mass is then formed into an elongated shape and allowed to cool to set to a solid state. The solid is then comminuted to obtain a powder having a desirable particle size, e.g. not more than 5% by weight through a 120-mesh sieve and not more than 5% by weight retained on a 14-mesh sieve.
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- Solvolysis of sterol tosylates in aqueous dimethylformamide
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It has been established that the heating of the sterol tosylates (1a - c) in aqueous dimethylformamide in the presence of sodium acetate leads to the formation of the 3α,5-cyclo-6β-alcohols (2), the sterols (3), the 3,5-dienes (4), and the sterol formates (5).
- Kovganko,Survilo
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p. 324 - 327
(2007/10/03)
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- 1-[2-(Trimethylsilyl)ethoxy]ethyl (SEE): A novel hybrid hydroxy-protecting group between 1-(ethoxy)ethyl (EE) and 2-(trimethylsilyl)ethoxymethyl (SEM)
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The highly versatile 1-[(2-trimethylsilyl)ethoxy]ethyl (SEE) group, readily obtainable from an alcohol and 2-(trimethylsilyl)ethyl vinyl ether in the presence of a catalytic amount of PPTS, has been developed for the protection of hydroxyl groups. Its deprotection can be achieved under virtually neutral conditions with the use of a fluoride ion source, thus allowing for effective protection of hydroxyl groups of compounds that contain acid- and/or base-sensitive functional groups.
- Wu, Junjun,Shull, Brian K.,Koreeda, Masato
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p. 3647 - 3650
(2007/10/03)
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- Process for the preparation of alcohols
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The present invention relates to a method to set free sterols from organic materials containing esters of such sterols, generally enriched distillation residues, or desodorisates by treating said organic material with ammonia and/or an amine and/or compound releases ammonia and/or amines while heated, the treament being carried out preferably at an elevated temperature, and under an elevated pressure.
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- REDUCTIVE CLEAVAGE OF t-BUTYLDIMETHYLSILYL ETHERS WITH SODIUM HYDRIDE
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t-Butyldimethylsilyl ethers are cleaved with sodium hydride in hexamethylphosphoric triamide (HMPA) or N,N'-dimethylpropyleneurea (DMPU).
- Shekhani, Mohammed Saleh,Khan, Mohammed Khalid,Mahmood, Khalid
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p. 6161 - 6162
(2007/10/02)
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- Sterols in Marine Invertebrates. Part 57. Stereostructure, Synthesis, and Acid-catalysed Isomerization of Hebesterol - A Biosynthetically Significant Cyclopropyl-containing Marine Sterol
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Three new cyclopropane-containing sterols hebesterol (11), petrostanol (8), and 23,24-dihydro-5α-calystanol (10) have been isolated from the sponge, Petrosia hebes, together with the principal sterol, petrosterol (7), and 21 known sterols.The structure elucidation of the new trace sterols was accomplished by spectroscopic methods and partial synthesis.Hebesterol (11) and its trans-diastereoisomers (31)-(33) have been synthesized and their acid-catalysed cyclopropane ring-opening studied.Each hebesterol isomer (11), (31)-(33) was correlated with the recently synthesized ficisterol isomers (5), (53), (56), and (58) of known absolute stereochemistry, thus leading to an unambiguous assignment of the absolute stereochemistry of hebesterol.The other products from the acid-catalysed isomerizations were characterized by spectroscopic methods, synthesis, and mechanistic considerations.Two of these products, (23R)-23-ethyldesmosterol (51) and (23S)-23-ethyldesmosterol (59), provided a relay to the absolute stereochemistry of the 23-ethylcholestanols, which had previously been synthesized without assignment of absolute stereochemistry.Hebesterol (11) is the key 'missing link' with the predicted stereochemistry in a proposed biosynthetic sequence encompassing the unusual marine sterols dihydrocalysterol (9), petrosterol (7), and ficisterol (5).
- Cho, Jin-Ho,Djerassi, Carl
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p. 1307 - 1318
(2007/10/02)
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- Side Chain Structural Requirement for Utilization of Sterols by the Silkworm for Growth and Development. Non-stereoselective Utilization of the 24-Stereoisomeric Pairs of 24-Alkylsterols
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Four C-24 epimeric pairs of 24-alkylsterols 1-8 were stereoselectively synthesized via orthoester Claisen rearrangement of the (22)R or (22S)-Δ23Z steroid derivatives (11 and 12).These compounds were tested on the silkworm larvae, Bombyx mori, in order to examine the relationship of the C-24 stereochemical arrangement and utilizability as a nutrient sterol.All of the tested sterols effectively supported the growth and development of the insect and were converted into cholesterol regardless of the C-24 configuration.Keywords - 24-alkylcholesterol; 24-alkyl-22-dehydrocholesterol; orthoester Claisen rearrangement; stereoselective synthesis; insect sterol; silkworm
- Fujimoto, Yoshinori,Kimura, Miki,Khalifa, Fathy A. M.,Ikekawa, Nobuo
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p. 4372 - 4381
(2007/10/02)
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- Constituents from Adina cordifolia
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Four compounds isolated from the stem of Adina cordifolia were identified as stigmasta-5,22-diene-3β-O-α-L-rhamnopyranosyl-(1 -> 4)-β-D-xylopyranoside, α-amyrin, octacosanol, and naringenin-7-methylether-4'-O-α-L-rhamnopyranoside on the basis of spectral and chemical evidence.
- Srivastava, Santosh K.
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p. 1827 - 1830
(2007/10/02)
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- Preparation of 3β-hydroxy-27-norcholest-5-ene-25-one and intermediates thereof
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A process for preparing 3β-hydroxy-27-norcholest-5-ene-25-one, a useful intermediate in the synthesis of 25-acetoxy vitamin D3, novel intermediates, and preparation thereof are disclosed.
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