GB489623A - Improvements in high vacuum distillation of materials containing sterols and related compounds - Google Patents
Improvements in high vacuum distillation of materials containing sterols and related compoundsInfo
- Publication number
- GB489623A GB489623A GB2624/37A GB262437A GB489623A GB 489623 A GB489623 A GB 489623A GB 2624/37 A GB2624/37 A GB 2624/37A GB 262437 A GB262437 A GB 262437A GB 489623 A GB489623 A GB 489623A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oil
- sterols
- cholesterol
- oils
- saponins
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229930182558 Sterol Natural products 0.000 title abstract 7
- 150000003432 sterols Chemical class 0.000 title abstract 7
- 235000003702 sterols Nutrition 0.000 title abstract 7
- 150000001875 compounds Chemical class 0.000 title abstract 5
- 238000005292 vacuum distillation Methods 0.000 title abstract 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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 abstract 12
- KZJWDPNRJALLNS-VJSFXXLFSA-N 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 abstract 8
- 235000012000 cholesterol Nutrition 0.000 abstract 6
- 239000003921 oil Substances 0.000 abstract 6
- 235000019198 oils Nutrition 0.000 abstract 6
- 239000002994 raw material Substances 0.000 abstract 6
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 abstract 4
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 abstract 4
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 abstract 4
- 239000003613 bile acid Substances 0.000 abstract 4
- -1 cinchocerotin Chemical class 0.000 abstract 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 4
- 229910052753 mercury Inorganic materials 0.000 abstract 4
- 229930182490 saponin Natural products 0.000 abstract 4
- 150000007949 saponins Chemical class 0.000 abstract 4
- 235000017709 saponins Nutrition 0.000 abstract 4
- 229950005143 sitosterol Drugs 0.000 abstract 4
- 239000010698 whale oil Substances 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 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 abstract 2
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 abstract 2
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 abstract 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 abstract 2
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 abstract 2
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 abstract 2
- 241000221751 Claviceps purpurea Species 0.000 abstract 2
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 abstract 2
- QRLVDLBMBULFAL-UHFFFAOYSA-N Digitonin Natural products CC1CCC2(OC1)OC3C(O)C4C5CCC6CC(OC7OC(CO)C(OC8OC(CO)C(O)C(OC9OCC(O)C(O)C9OC%10OC(CO)C(O)C(OC%11OC(CO)C(O)C(O)C%11O)C%10O)C8O)C(O)C7O)C(O)CC6(C)C5CCC4(C)C3C2C QRLVDLBMBULFAL-UHFFFAOYSA-N 0.000 abstract 2
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- 241000418087 Physostigma venenosum Species 0.000 abstract 2
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 abstract 2
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 abstract 2
- 239000010775 animal oil Substances 0.000 abstract 2
- 239000012164 animal wax Substances 0.000 abstract 2
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 abstract 2
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 abstract 2
- 239000012174 chinese wax Substances 0.000 abstract 2
- 150000001829 cholanes Chemical class 0.000 abstract 2
- QYIXCDOBOSTCEI-NWKZBHTNSA-N coprostanol Chemical compound C([C@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-NWKZBHTNSA-N 0.000 abstract 2
- 239000002385 cottonseed oil Substances 0.000 abstract 2
- 235000012343 cottonseed oil Nutrition 0.000 abstract 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 abstract 2
- UVYVLBIGDKGWPX-UHFFFAOYSA-N digitonine Natural products CC1C(C2(CCC3C4(C)CC(O)C(OC5C(C(O)C(OC6C(C(OC7C(C(O)C(O)CO7)O)C(O)C(CO)O6)OC6C(C(OC7C(C(O)C(O)C(CO)O7)O)C(O)C(CO)O6)O)C(CO)O5)O)CC4CCC3C2C2O)C)C2OC11CCC(C)CO1 UVYVLBIGDKGWPX-UHFFFAOYSA-N 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 abstract 2
- DNVPQKQSNYMLRS-SOWFXMKYSA-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-SOWFXMKYSA-N 0.000 abstract 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003925 fat Substances 0.000 abstract 2
- 229940084434 fungoid Drugs 0.000 abstract 2
- 230000012010 growth Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229940068065 phytosterols Drugs 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- 235000015500 sitosterol Nutrition 0.000 abstract 2
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 abstract 2
- 238000000638 solvent extraction Methods 0.000 abstract 2
- 229940031439 squalene Drugs 0.000 abstract 2
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 abstract 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 abstract 2
- 235000016831 stigmasterol Nutrition 0.000 abstract 2
- 229940032091 stigmasterol Drugs 0.000 abstract 2
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 2
- 239000008158 vegetable oil Substances 0.000 abstract 2
- 239000003039 volatile agent Substances 0.000 abstract 2
- 239000010497 wheat germ oil Substances 0.000 abstract 2
- RPKLZQLYODPWTM-KBMWBBLPSA-N cholanoic acid Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(O)=O)C)[C@@]1(C)CC2 RPKLZQLYODPWTM-KBMWBBLPSA-N 0.000 abstract 1
- 150000001841 cholesterols Chemical class 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
Raw material containing a compound having a cholane nucleus such as sterols, saponins and bile acids, is subjected to short-path high-vacuum distillation to separate the substance therefrom, the compound then being purified. The raw materials specified comprise animal oils and waxes, such as whale oil, faecal fats and oils and chinese wax; vegetable oils, such as soya bean oil, cotton-seed oil, wheat germ oil and calabar bean oil; and fungoid growths, such as ergot of rye, each of which groups are sources of zoösterols, phytosterols and mycosterols respectively. Particular sterols which may thus be isolated comprise cholesterols, cinchol, coprosterol, stigmasterol, sitosterol, and ergosterol. Other sterols such as cinchocerotin, quebrachol and rhamnol, saponins, such as digitonin, and bile acids, such as cholanic acid may also be separated from the raw materials containing them. In a preferred apparatus the distilling surface comprises an internally-heated hollow vertical dome with a spirally - corrugated surface. The distance between distilling and condensing surfaces may vary between ,25 inch and 10 feet and the degree of vacuum correspondingly between 8 microns and ,01 micron of mercury. Temperatures may range between 70 and 325 DEG C. In an example, clarified whale oil was distilled at temperatures of 90 to 220 DEG C. and pressures of ,001 to ,003 mm. of mercury. A first fraction containing free acids, squalene and other volatiles was withdrawn, and at 120-160 DEG C. a mixture of cholesterol and cholesteryl esters distilled over. The cholesterol was extracted with acetoacetic ester and recrystallized. Purification may comprise saponification of the fraction followed by solvent extraction and distillation of the latter. Specification 487,697 is referred to.ALSO:Raw material containing a compound having a cholane nucleus such as sterols, saponins, and bile acids is subjected to short path high vacuum distillation to separate the substance therefrom, the compound then being purified. The raw materials specified comprise animal oils and waxes such as whale oil, faecal fats and oils and chinese wax; vegetable oils, such as soya bean oil, cotton-seed oil, wheat germ oil and calabar bean oil; and fungoid growths, such as ergot of rye, each of which groups are sources of zoösterols, phytosterols and mycosterols respectively. Particular sterols which may thus be isolated comprise cholesterol, cinchol, coprosterol, stigmasterol, sitosterol and ergosterol. Other sterols such as cinchocerotin, quebrachol and rhamnol, saponins, such as digitonin, and bile acids such as chelanic acid may also be separated from the raw materials containing them. The distance between distilling and condensing surfaces may vary between ,25 inches and 10 feet and the degree of vacuum correspondingly between 8 microns and ,01 microns of mercury. Temperatures may range between 70 and 325 DEG C. In an example, clarified whale oil was distilled at temperatures of 90 to 220 DEG C. and pressures of ,001 to ,003 millimetres of mercury. A first fraction containing free acids, squalene and other volatiles was withdrawn, and at 120-160 DEG C. a mixture of cholesterol and cholesteryl esters distilled over. The cholesterol was extracted with acetoacetic ester and recrystallized. Purification may comprise saponification of the fraction followed by solvent extraction and distillation of the latter. Specification 487,697 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US489623XA | 1936-02-06 | 1936-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB489623A true GB489623A (en) | 1938-07-29 |
Family
ID=21957365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2624/37A Expired GB489623A (en) | 1936-02-06 | 1937-01-29 | Improvements in high vacuum distillation of materials containing sterols and related compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB489623A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7632530B2 (en) | 2005-11-08 | 2009-12-15 | Council Of Scientific And Industrial Research | Process for the preparation of high purity phytosterols |
| WO2016096989A1 (en) * | 2014-12-19 | 2016-06-23 | Dsm Ip Assets B.V. | Method of extracting cholesterol from fish oil residue |
| US10190074B1 (en) | 2018-02-14 | 2019-01-29 | Golden Omega S.A. | Composition comprising cholesterol |
| US10196586B1 (en) | 2018-02-14 | 2019-02-05 | Golden Omega S.A. | Feed ingredient |
| US10196583B1 (en) | 2018-02-14 | 2019-02-05 | Alejandro Markovits Rojas | Fish oil cholesterol |
| WO2022069923A1 (en) | 2020-09-30 | 2022-04-07 | Naturmega S.A. | Method for obtaining cholesterol present in fish oil |
-
1937
- 1937-01-29 GB GB2624/37A patent/GB489623A/en not_active Expired
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7632530B2 (en) | 2005-11-08 | 2009-12-15 | Council Of Scientific And Industrial Research | Process for the preparation of high purity phytosterols |
| WO2016096989A1 (en) * | 2014-12-19 | 2016-06-23 | Dsm Ip Assets B.V. | Method of extracting cholesterol from fish oil residue |
| WO2019159028A1 (en) | 2018-02-14 | 2019-08-22 | Golden Omega S.A. | Composition comprising cholesterol |
| US10196586B1 (en) | 2018-02-14 | 2019-02-05 | Golden Omega S.A. | Feed ingredient |
| US10196583B1 (en) | 2018-02-14 | 2019-02-05 | Alejandro Markovits Rojas | Fish oil cholesterol |
| WO2019159027A1 (en) | 2018-02-14 | 2019-08-22 | Golden Omega S.A. | Feed ingredient |
| US10190074B1 (en) | 2018-02-14 | 2019-01-29 | Golden Omega S.A. | Composition comprising cholesterol |
| CN110150474A (en) * | 2018-02-14 | 2019-08-23 | 金欧米茄公司 | Feed ingredient |
| CN110150473A (en) * | 2018-02-14 | 2019-08-23 | 金欧米茄公司 | Include cholesteric composition |
| EP3666867A1 (en) | 2018-02-14 | 2020-06-17 | Alejandro Markovits Rojas | Fish oil cholesterol |
| CN110150474B (en) * | 2018-02-14 | 2022-12-09 | 金欧米茄公司 | Feed ingredient |
| CN110150473B (en) * | 2018-02-14 | 2022-12-13 | 金欧米茄公司 | Composition comprising cholesterol |
| WO2022069923A1 (en) | 2020-09-30 | 2022-04-07 | Naturmega S.A. | Method for obtaining cholesterol present in fish oil |
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