CH529713A - Verfahren zur Herstellung von Crocetinestern - Google Patents
Verfahren zur Herstellung von CrocetinesternInfo
- Publication number
- CH529713A CH529713A CH520572A CH520572A CH529713A CH 529713 A CH529713 A CH 529713A CH 520572 A CH520572 A CH 520572A CH 520572 A CH520572 A CH 520572A CH 529713 A CH529713 A CH 529713A
- Authority
- CH
- Switzerland
- Prior art keywords
- esters
- crocetine
- ester
- crocetin
- alkyl
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 17
- 238000004040 coloring Methods 0.000 title abstract description 5
- 235000013305 food Nutrition 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- PANKHBYNKQNAHN-MQQNZMFNSA-N crocetin Chemical class OC(=O)C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)C(O)=O PANKHBYNKQNAHN-MQQNZMFNSA-N 0.000 claims description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QXJSYJRWEUENRT-PSAUJTBTSA-N 4,9-dimethyldodeca-2,4,6,8,10-pentaenedial Chemical compound O=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=O QXJSYJRWEUENRT-PSAUJTBTSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- -1 palmitoyl ascorbate sodium salt Chemical class 0.000 abstract description 8
- 235000013736 caramel Nutrition 0.000 abstract description 2
- 239000003995 emulsifying agent Substances 0.000 abstract description 2
- 235000015243 ice cream Nutrition 0.000 abstract description 2
- 239000008268 mayonnaise Substances 0.000 abstract description 2
- 235000010746 mayonnaise Nutrition 0.000 abstract description 2
- 235000013618 yogurt Nutrition 0.000 abstract description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 2
- 235000015203 fruit juice Nutrition 0.000 abstract 2
- 239000004150 EU approved colour Substances 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- 229960005070 ascorbic acid Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- PANKHBYNKQNAHN-JTBLXSOISA-N Crocetin Natural products OC(=O)C(\C)=C/C=C/C(/C)=C\C=C\C=C(\C)/C=C/C=C(/C)C(O)=O PANKHBYNKQNAHN-JTBLXSOISA-N 0.000 description 5
- PANKHBYNKQNAHN-JUMCEFIXSA-N carotenoid dicarboxylic acid Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C(=O)O)C=CC=C(/C)C(=O)O PANKHBYNKQNAHN-JUMCEFIXSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000021466 carotenoid Nutrition 0.000 description 4
- 150000001747 carotenoids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- FDSDTBUPSURDBL-LOFNIBRQSA-N canthaxanthin Chemical compound CC=1C(=O)CCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)CCC1(C)C FDSDTBUPSURDBL-LOFNIBRQSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- SEBIKDIMAPSUBY-ARYZWOCPSA-N Crocin Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)OC(=O)C(C)=CC=CC(C)=C\C=C\C=C(/C)\C=C\C=C(C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1)O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SEBIKDIMAPSUBY-ARYZWOCPSA-N 0.000 description 1
- SEBIKDIMAPSUBY-JAUCNNNOSA-N Crocin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C(=O)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C=CC=C(/C)C(=O)OC3OC(COC4OC(CO)C(O)C(O)C4O)C(O)C(O)C3O SEBIKDIMAPSUBY-JAUCNNNOSA-N 0.000 description 1
- 244000124209 Crocus sativus Species 0.000 description 1
- 235000015655 Crocus sativus Nutrition 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- OOUTWVMJGMVRQF-DOYZGLONSA-N Phoenicoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C(=O)C(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)C(=O)CCC2(C)C OOUTWVMJGMVRQF-DOYZGLONSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000012682 canthaxanthin Nutrition 0.000 description 1
- 239000001659 canthaxanthin Substances 0.000 description 1
- 229940008033 canthaxanthin Drugs 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RXTSHIDRCASANN-UHFFFAOYSA-N dodecyl 2-bromopropanoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)Br RXTSHIDRCASANN-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 235000015201 grapefruit juice Nutrition 0.000 description 1
- LOGGHEZVYPCZGT-UHFFFAOYSA-N hexadecyl 2-bromopropanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)Br LOGGHEZVYPCZGT-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 235000015122 lemonade Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000013974 saffron Nutrition 0.000 description 1
- 239000004248 saffron Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/47—Addition of dyes or pigments, e.g. in combination with optical brighteners using synthetic organic dyes or pigments not covered by groups A23L5/43 - A23L5/46
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/602—Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Biochemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Non-Alcoholic Beverages (AREA)
- Confectionery (AREA)
- Luminescent Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH520572A CH529713A (de) | 1969-10-31 | 1969-10-31 | Verfahren zur Herstellung von Crocetinestern |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1624469A CH539677A (de) | 1969-10-31 | 1969-10-31 | Verfahren zur Herstellung von wasserdispergierbaren Färbepräparaten |
| CH520572A CH529713A (de) | 1969-10-31 | 1969-10-31 | Verfahren zur Herstellung von Crocetinestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH529713A true CH529713A (de) | 1972-10-31 |
Family
ID=4415634
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1624469A CH539677A (de) | 1969-10-31 | 1969-10-31 | Verfahren zur Herstellung von wasserdispergierbaren Färbepräparaten |
| CH520572A CH529713A (de) | 1969-10-31 | 1969-10-31 | Verfahren zur Herstellung von Crocetinestern |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1624469A CH539677A (de) | 1969-10-31 | 1969-10-31 | Verfahren zur Herstellung von wasserdispergierbaren Färbepräparaten |
Country Status (15)
| Country | Link |
|---|---|
| AT (2) | AT298210B (fr) |
| BE (1) | BE758244A (fr) |
| CA (1) | CA966147A (fr) |
| CH (2) | CH539677A (fr) |
| DE (1) | DE2053381A1 (fr) |
| ES (2) | ES385045A1 (fr) |
| FR (1) | FR2066721A5 (fr) |
| GB (1) | GB1284350A (fr) |
| HU (1) | HU166240B (fr) |
| IE (1) | IE34667B1 (fr) |
| IL (1) | IL35408A (fr) |
| IT (1) | IT1003009B (fr) |
| NL (1) | NL7013551A (fr) |
| TR (1) | TR16822A (fr) |
| ZA (1) | ZA706636B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3610191A1 (de) * | 1986-03-26 | 1987-10-01 | Basf Ag | Verfahren zur herstellung von feinteiligen, wasserdispergierbaren carotinoid-praeparationen |
| EP1511811A2 (fr) * | 2002-05-30 | 2005-03-09 | Phares Pharmaceutical Research N.V. | Compositions de pigments solubles dans l'huile |
| ES2602812T3 (es) * | 2008-12-01 | 2017-02-22 | Aquanova Ag | Protección contra la oxidación integrada micelarmente para colorantes naturales |
-
0
- BE BE758244D patent/BE758244A/fr unknown
-
1969
- 1969-10-31 CH CH1624469A patent/CH539677A/de not_active IP Right Cessation
- 1969-10-31 CH CH520572A patent/CH529713A/de not_active IP Right Cessation
-
1970
- 1970-09-14 NL NL7013551A patent/NL7013551A/xx unknown
- 1970-09-16 HU HUHO1325A patent/HU166240B/hu unknown
- 1970-09-29 ZA ZA706636*A patent/ZA706636B/xx unknown
- 1970-10-07 IL IL35408A patent/IL35408A/xx unknown
- 1970-10-17 IT IT31105/70A patent/IT1003009B/it active
- 1970-10-20 TR TR16822A patent/TR16822A/xx unknown
- 1970-10-27 CA CA096,655A patent/CA966147A/en not_active Expired
- 1970-10-28 IE IE1377/70A patent/IE34667B1/xx unknown
- 1970-10-29 FR FR7039065A patent/FR2066721A5/fr not_active Expired
- 1970-10-29 GB GB51514/70A patent/GB1284350A/en not_active Expired
- 1970-10-30 ES ES385045A patent/ES385045A1/es not_active Expired
- 1970-10-30 AT AT978670A patent/AT298210B/de not_active IP Right Cessation
- 1970-10-30 AT AT181471A patent/AT303695B/de not_active IP Right Cessation
- 1970-10-30 DE DE19702053381 patent/DE2053381A1/de active Pending
-
1972
- 1972-05-17 ES ES402817A patent/ES402817A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE34667B1 (en) | 1975-07-09 |
| IL35408A (en) | 1974-11-29 |
| FR2066721A5 (fr) | 1971-08-06 |
| IE34667L (en) | 1971-04-30 |
| DE2053381A1 (de) | 1971-05-06 |
| CA966147A (en) | 1975-04-15 |
| ZA706636B (en) | 1971-06-30 |
| ES385045A1 (es) | 1973-03-16 |
| AT303695B (de) | 1972-12-11 |
| IL35408A0 (en) | 1970-12-24 |
| CH539677A (de) | 1973-07-31 |
| ES402817A1 (es) | 1975-04-16 |
| GB1284350A (en) | 1972-08-09 |
| IT1003009B (it) | 1976-06-10 |
| TR16822A (tr) | 1973-07-01 |
| HU166240B (fr) | 1975-02-28 |
| NL7013551A (fr) | 1971-05-04 |
| AT298210B (de) | 1972-04-25 |
| BE758244A (fr) | 1971-04-01 |
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