BE447605A

BE447605A -

Info

Publication number: BE447605A
Authority: BE; Belgium
Prior art keywords: sterols; adducts; adduct; water; salt
Prior art date

Application number

Other languages

English (en)

French (fr)

Publication of BE447605A publication Critical patent/BE447605A/fr

Links

229910001868 water Inorganic materials 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
150000003432 sterols Chemical class 0.000 claims description 31
235000003702 sterols Nutrition 0.000 claims description 31
239000011780 sodium chloride Substances 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
238000000034 method Methods 0.000 claims description 19
210000002268 Wool Anatomy 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
238000003756 stirring Methods 0.000 claims description 14
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
239000000463 material Substances 0.000 claims description 10
239000002994 raw material Substances 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 6
235000014113 dietary fatty acids Nutrition 0.000 claims description 6
239000000194 fatty acid Substances 0.000 claims description 6
150000004665 fatty acids Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
238000000746 purification Methods 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
238000007792 addition Methods 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
238000005755 formation reaction Methods 0.000 claims description 5
GLFNIEUTAYBVOC-UHFFFAOYSA-L MANGANESE CHLORIDE Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
230000001476 alcoholic Effects 0.000 claims description 4
-1 aliphatic alcohols Chemical class 0.000 claims description 4
239000011565 manganese chloride Substances 0.000 claims description 4
235000002867 manganese chloride Nutrition 0.000 claims description 4
229940099607 manganese chloride Drugs 0.000 claims description 4
239000000344 soap Substances 0.000 claims description 4
239000011592 zinc chloride Substances 0.000 claims description 4
235000005074 zinc chloride Nutrition 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
150000002989 phenols Chemical class 0.000 claims description 3
150000002696 manganese Chemical class 0.000 claims description 2
159000000007 calcium salts Chemical class 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
230000000737 periodic Effects 0.000 claims 1
HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 72
229940107161 Cholesterol Drugs 0.000 description 36
235000012000 cholesterol Nutrition 0.000 description 36
235000019441 ethanol Nutrition 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
150000001298 alcohols Chemical class 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
NHTMVDHEPJAVLT-UHFFFAOYSA-N isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 7
KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000001110 calcium chloride Substances 0.000 description 5
229910001628 calcium chloride Inorganic materials 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000005712 crystallization Effects 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 3
210000004556 Brain Anatomy 0.000 description 3
NNBZCPXTIHJBJL-UHFFFAOYSA-N Decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 3
DNVPQKQSNYMLRS-APGDWVJJSA-N Ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 description 3
DNVPQKQSNYMLRS-LNHMRCHQSA-N Ergosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3C([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)=CC=2)CC1 DNVPQKQSNYMLRS-LNHMRCHQSA-N 0.000 description 3
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
235000015500 sitosterol Nutrition 0.000 description 3
229950005143 sitosterol Drugs 0.000 description 3
KZJWDPNRJALLNS-VJSFXXLFSA-N β-Sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N Cetyl alcohol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
UVYVLBIGDKGWPX-SPPYGRLSSA-N Digitonin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@H]2[C@@H](O)C[C@]3(C)[C@@H]4[C@H]([C@@H]5[C@H](O)[C@@H]6O[C@]7([C@@H](C)[C@@H]6[C@@]5(C)CC4)OC[C@H](C)CC7)CC[C@H]3C2)O[C@H]1CO)[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)[C@H](O)[C@@H](CO)O2)[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](O)CO2)[C@H](O)[C@@H](CO)O1 UVYVLBIGDKGWPX-SPPYGRLSSA-N 0.000 description 2
CCGKOQOJPYTBIH-UHFFFAOYSA-N Ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
229940032091 Stigmasterol Drugs 0.000 description 2
HCXVJBMSMIARIN-MFBJGPNFSA-N Stigmasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 HCXVJBMSMIARIN-MFBJGPNFSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
235000015278 beef Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
UVYVLBIGDKGWPX-KUAJCENISA-N digitonin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](O[C@H]5[C@@H]([C@@H](O)[C@@H](O[C@H]6[C@@H]([C@@H](O[C@H]7[C@@H]([C@@H](O)[C@H](O)CO7)O)[C@H](O)[C@@H](CO)O6)O[C@H]6[C@@H]([C@@H](O[C@H]7[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O7)O)[C@@H](O)[C@@H](CO)O6)O)[C@@H](CO)O5)O)C[C@@H]4CC[C@H]3[C@@H]2[C@@H]1O)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 UVYVLBIGDKGWPX-KUAJCENISA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 2
235000016831 stigmasterol Nutrition 0.000 description 2
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
JLDSOYXADOWAKB-UHFFFAOYSA-N Aluminium nitrate Chemical compound [Al+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O JLDSOYXADOWAKB-UHFFFAOYSA-N 0.000 description 1
239000005996 Blood meal Substances 0.000 description 1
YKYOUMDCQGMQQO-UHFFFAOYSA-L Cadmium chloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 1
OTVRYZXVVMZHHW-DPAQBDIFSA-N Cholesteryl chloride Chemical compound C1C=C2C[C@@H](Cl)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 OTVRYZXVVMZHHW-DPAQBDIFSA-N 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L Cobalt(II) chloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
210000002969 Egg Yolk Anatomy 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
TZIHFWKZFHZASV-UHFFFAOYSA-N Methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 1
241000611009 Nematalosa come Species 0.000 description 1
210000004940 Nucleus Anatomy 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
210000000278 Spinal Cord Anatomy 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
240000008529 Triticum aestivum Species 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052925 anhydrite Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium Chemical class [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
150000004653 carbonic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000013345 egg yolk Nutrition 0.000 description 1
230000002349 favourable Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Chemical class 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
230000001264 neutralization Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
238000005201 scrubbing Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910052718 tin Chemical class 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
235000021307 wheat Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Chemical class 0.000 description 1