IL26591A - Process for the manufacture of tocopherol and derivatives thereof - Google Patents
Process for the manufacture of tocopherol and derivatives thereofInfo
- Publication number
- IL26591A IL26591A IL26591A IL2659166A IL26591A IL 26591 A IL26591 A IL 26591A IL 26591 A IL26591 A IL 26591A IL 2659166 A IL2659166 A IL 2659166A IL 26591 A IL26591 A IL 26591A
- Authority
- IL
- Israel
- Prior art keywords
- cyclization
- symbol
- hydrogen
- group
- member selected
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 title description 12
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 title description 8
- 229930003799 tocopherol Natural products 0.000 title description 5
- 239000011732 tocopherol Substances 0.000 title description 5
- 235000010384 tocopherol Nutrition 0.000 title description 2
- 229960001295 tocopherol Drugs 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000007363 ring formation reaction Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003016 chromanyl group Chemical class O1C(CCC2=CC=CC=C12)* 0.000 claims 3
- 150000004820 halides Chemical class 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- -1 for example Substances 0.000 description 6
- 229930003427 Vitamin E Natural products 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 5
- 239000011709 vitamin E Substances 0.000 description 5
- 235000019165 vitamin E Nutrition 0.000 description 5
- 229940046009 vitamin E Drugs 0.000 description 5
- 150000001843 chromanes Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000020071 rectified spirit Nutrition 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 235000019149 tocopherols Nutrition 0.000 description 3
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 150000003611 tocopherol derivatives Chemical class 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- QIXDHVDGPXBRRD-UHFFFAOYSA-N trimethyl-p-benzoquinone Natural products CC1=CC(=O)C(C)=C(C)C1=O QIXDHVDGPXBRRD-UHFFFAOYSA-N 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1404965A CH475977A (de) | 1965-10-12 | 1965-10-12 | Verfahren zur Herstellung eines Chromanderivates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL26591A true IL26591A (en) | 1970-07-19 |
Family
ID=4397512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL26591A IL26591A (en) | 1965-10-12 | 1966-09-28 | Process for the manufacture of tocopherol and derivatives thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3455959A (OSRAM) |
| BE (1) | BE687927A (OSRAM) |
| BR (1) | BR6683553D0 (OSRAM) |
| CH (1) | CH475977A (OSRAM) |
| DK (2) | DK128075B (OSRAM) |
| ES (1) | ES332169A1 (OSRAM) |
| FR (1) | FR1502907A (OSRAM) |
| GB (1) | GB1102199A (OSRAM) |
| IL (1) | IL26591A (OSRAM) |
| SE (1) | SE323084B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6020388B2 (ja) * | 1974-07-18 | 1985-05-21 | エーザイ株式会社 | ビタミンｅ脂肪族カルボン酸エステルの合成法 |
| JPS607993B2 (ja) * | 1978-01-12 | 1985-02-28 | 株式会社クラレ | ｄｌ−α−トコフエロ−ルの製造方法 |
| DE3044109A1 (de) * | 1980-11-24 | 1982-06-24 | Basf Ag, 6700 Ludwigshafen | Chromanderivate sowie verfahren zu deren herstellung |
| JPS57136582A (en) * | 1981-02-19 | 1982-08-23 | Eisai Co Ltd | Preparation of optically active alpha-tocopherol |
| US11679341B2 (en) * | 2020-04-30 | 2023-06-20 | Waters Technologies Corporation | Differentiation of natural vitamin E from synthetic vitamin E and quantification of tocopherols by supercritical fluid chromatography |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH376898A (de) * | 1958-08-07 | 1964-04-30 | Hoffmann La Roche | Verfahren zur Herstellung von in 6-Stellung substituierten 2,3-Dimethoxy-5-methyl-benzohydrochinonen-(1,4) bzw.-benzochinonen-(1,4) |
| US3064012A (en) * | 1960-07-20 | 1962-11-13 | Merck & Co Inc | Derivatives of coenzyme q10 |
| DE1300571B (de) * | 1963-12-20 | 1969-08-07 | Merck & Co Inc | Verfahren zur Herstellung von 7, 8-Dimethoxy-2, 5-dimethyl-6-oxy-2-(4', 8', 12'-trimethyltridecyl)-chroman |
-
1965
- 1965-10-12 CH CH1404965A patent/CH475977A/de not_active IP Right Cessation
-
1966
- 1966-04-07 BE BE687927D patent/BE687927A/xx unknown
- 1966-09-21 US US580877A patent/US3455959A/en not_active Expired - Lifetime
- 1966-09-28 IL IL26591A patent/IL26591A/en unknown
- 1966-10-10 FR FR79271A patent/FR1502907A/fr not_active Expired
- 1966-10-11 BR BR183553/66A patent/BR6683553D0/pt unknown
- 1966-10-11 ES ES0332169A patent/ES332169A1/es not_active Expired
- 1966-10-11 GB GB45454/66A patent/GB1102199A/en not_active Expired
- 1966-10-12 SE SE13795/66A patent/SE323084B/xx unknown
- 1966-10-12 DK DK527466AA patent/DK128075B/da unknown
-
1970
- 1970-04-09 DK DK178670AA patent/DK128004B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1543669B2 (de) | 1976-01-02 |
| DK128004B (da) | 1974-02-18 |
| DK128075B (da) | 1974-02-25 |
| DE1543669A1 (de) | 1969-10-09 |
| GB1102199A (en) | 1968-02-07 |
| BE687927A (OSRAM) | 1967-04-07 |
| BR6683553D0 (pt) | 1973-12-04 |
| ES332169A1 (es) | 1967-07-16 |
| CH475977A (de) | 1969-07-31 |
| US3455959A (en) | 1969-07-15 |
| SE323084B (OSRAM) | 1970-04-27 |
| FR1502907A (fr) | 1967-11-24 |
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