JP3547741B2 - 高シス−β−カロチン組成物 - Google Patents
高シス−β−カロチン組成物 Download PDFInfo
- Publication number
- JP3547741B2 JP3547741B2 JP50003894A JP50003894A JP3547741B2 JP 3547741 B2 JP3547741 B2 JP 3547741B2 JP 50003894 A JP50003894 A JP 50003894A JP 50003894 A JP50003894 A JP 50003894A JP 3547741 B2 JP3547741 B2 JP 3547741B2
- Authority
- JP
- Japan
- Prior art keywords
- carotenoid
- cis
- carotene
- composition
- composition according
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 239000011648 beta-carotene Substances 0.000 title claims abstract description 56
- 229960002747 betacarotene Drugs 0.000 title claims abstract description 47
- 235000021466 carotenoid Nutrition 0.000 claims abstract description 55
- 150000001747 carotenoids Chemical class 0.000 claims abstract description 52
- 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 claims abstract description 36
- OENHQHLEOONYIE-BVZAMQQESA-N 9-cis-beta-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-BVZAMQQESA-N 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 18
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- 239000003921 oil Substances 0.000 claims description 12
- 235000019198 oils Nutrition 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 241000195633 Dunaliella salina Species 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 7
- 241000196324 Embryophyta Species 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- 239000003549 soybean oil Substances 0.000 claims description 5
- 235000012424 soybean oil Nutrition 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002199 base oil Substances 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 2
- 241000219104 Cucurbitaceae Species 0.000 claims description 2
- 239000004258 Ethoxyquin Substances 0.000 claims description 2
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 2
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 2
- 240000007472 Leucaena leucocephala Species 0.000 claims description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 claims description 2
- 244000018633 Prunus armeniaca Species 0.000 claims description 2
- 235000009827 Prunus armeniaca Nutrition 0.000 claims description 2
- 235000010385 ascorbyl palmitate Nutrition 0.000 claims description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical group COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 claims description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 235000019285 ethoxyquin Nutrition 0.000 claims description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940093500 ethoxyquin Drugs 0.000 claims description 2
- 235000021323 fish oil Nutrition 0.000 claims description 2
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- 239000012528 membrane Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
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- 235000010388 propyl gallate Nutrition 0.000 claims description 2
- 239000000473 propyl gallate Substances 0.000 claims description 2
- 229940075579 propyl gallate Drugs 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- 229930003799 tocopherol Natural products 0.000 claims description 2
- 239000011732 tocopherol Substances 0.000 claims description 2
- 239000000341 volatile oil Substances 0.000 claims description 2
- -1 trans-isomer carotenoid Chemical class 0.000 claims 3
- 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 claims 1
- 235000010384 tocopherol Nutrition 0.000 claims 1
- 229960001295 tocopherol Drugs 0.000 claims 1
- 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 claims 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 abstract description 37
- 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 abstract description 37
- 235000013734 beta-carotene Nutrition 0.000 abstract description 35
- 239000013078 crystal Substances 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- ANVAOWXLWRTKGA-XHGAXZNDSA-N all-trans-alpha-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=CC1C(C)=CCCC1(C)C ANVAOWXLWRTKGA-XHGAXZNDSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000005445 natural material Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 241000195493 Cryptophyta Species 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 150000001746 carotenes Chemical class 0.000 description 3
- 235000005473 carotenes Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 3
- YVLPJIGOMTXXLP-UHFFFAOYSA-N 15-cis-phytoene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CC=CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C YVLPJIGOMTXXLP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- 235000015872 dietary supplement Nutrition 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- YVLPJIGOMTXXLP-UUKUAVTLSA-N 15,15'-cis-Phytoene Natural products C(=C\C=C/C=C(\CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)/C)(\CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)/C YVLPJIGOMTXXLP-UUKUAVTLSA-N 0.000 description 1
- YVLPJIGOMTXXLP-BAHRDPFUSA-N 15Z-phytoene Natural products CC(=CCCC(=CCCC(=CCCC(=CC=C/C=C(C)/CCC=C(/C)CCC=C(/C)CCC=C(C)C)C)C)C)C YVLPJIGOMTXXLP-BAHRDPFUSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000008238 biochemical pathway Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 230000004060 metabolic process Effects 0.000 description 1
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- 210000003463 organelle Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 235000011765 phytoene Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
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- 230000003134 recirculating effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
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- 238000002798 spectrophotometry method Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 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 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/15—Vitamins
- A23L33/155—Vitamins A or D
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
- A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
-
- 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
- A61K31/01—Hydrocarbons
- A61K31/015—Hydrocarbons carbocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Mycology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPL278992 | 1992-06-04 | ||
| PCT/AU1993/000267 WO1993024454A1 (en) | 1992-06-04 | 1993-06-04 | High cis beta-carotene composition |
| AU2789 | 1998-04-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07506837A JPH07506837A (ja) | 1995-07-27 |
| JP3547741B2 true JP3547741B2 (ja) | 2004-07-28 |
Family
ID=3776206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50003894A Expired - Fee Related JP3547741B2 (ja) | 1992-06-04 | 1993-06-04 | 高シス−β−カロチン組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5612485A (enExample) |
| EP (1) | EP0643692B1 (enExample) |
| JP (1) | JP3547741B2 (enExample) |
| AT (1) | ATE186905T1 (enExample) |
| DE (1) | DE69327100T2 (enExample) |
| WO (1) | WO1993024454A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06501695A (ja) * | 1990-10-01 | 1994-02-24 | ブリガム・アンド・ウイメンズ・ホスピタル | 主要血管事象を抑制するためのベータ−カロテン及びビタミンｅ療法 |
| US6132790A (en) * | 1991-09-06 | 2000-10-17 | Betatene Limited | Carotenoid composition |
| ES2149264T3 (es) * | 1993-03-22 | 2000-11-01 | Cognis Australia Pty Ltd | Agente terapeutico para el tratamiento de melanomas. |
| ES2178651T3 (es) * | 1993-03-22 | 2003-01-01 | Cognis Australia Pty Ltd | Compuestos carotenoides terapeuticos deispersables en agua. |
| ES2061401B1 (es) * | 1993-04-02 | 1995-06-16 | Francisco Tejedor Garcia S A | Embutidos enriquecidos, especialmente sobrasada. |
| IL119224A (en) * | 1996-09-09 | 2002-11-10 | Hadasit Med Res Service | Medicament for protection from effects of irradiation |
| JPH11187894A (ja) * | 1997-12-26 | 1999-07-13 | Oyo Seikagaku Kenkyusho | 高純度 ９−シス−β−カロチン含有組成物及びその製法 |
| JP2004038515A (ja) * | 2002-07-03 | 2004-02-05 | Sanyo Electric Co Ltd | データ記録装置 |
| CN101845009B (zh) | 2002-07-29 | 2012-10-03 | 卡达克斯药物公司 | 用于抑制和改善疾病的类胡萝卜素结构类似物 |
| US20050026874A1 (en) * | 2002-07-29 | 2005-02-03 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for the inhibition and amelioration of liver disease |
| US20050059659A1 (en) * | 2002-07-29 | 2005-03-17 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for controlling C-reactive protein levels |
| US20050148517A1 (en) * | 2002-07-29 | 2005-07-07 | Lockwood Samuel F. | Carotenoid ether analogs or derivatives for controlling connexin 43 expression |
| US20050059635A1 (en) * | 2002-07-29 | 2005-03-17 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for controlling C-reactive protein levels |
| US20050009788A1 (en) * | 2002-07-29 | 2005-01-13 | Lockwood Samuel Fournier | Carotenoid ester analogs or derivatives for controlling connexin 43 expression |
| US20050049248A1 (en) * | 2002-07-29 | 2005-03-03 | Lockwood Samuel Fournier | Carotenoid ether analogs or derivatives for controlling C-reactive protein levels |
| US7320997B2 (en) * | 2002-07-29 | 2008-01-22 | Cardax Pharmaceuticals, Inc. | Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease |
| US7763649B2 (en) * | 2002-07-29 | 2010-07-27 | Cardax Pharmaceuticals, Inc. | Carotenoid analogs or derivatives for controlling connexin 43 expression |
| US7521584B2 (en) * | 2002-07-29 | 2009-04-21 | Cardax Pharmaceuticals, Inc. | Carotenoid analogs or derivatives for the inhibition and amelioration of disease |
| US7345091B2 (en) * | 2002-07-29 | 2008-03-18 | Cardax Pharmaceuticals, Inc. | Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
| US7375133B2 (en) * | 2002-07-29 | 2008-05-20 | Cardax Pharmaceuticals, Inc. | Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
| US20050143475A1 (en) * | 2002-07-29 | 2005-06-30 | Lockwood Samuel F. | Carotenoid analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury |
| US7723327B2 (en) * | 2002-07-29 | 2010-05-25 | Cardax Pharmaceuticals, Inc. | Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease |
| US20050004235A1 (en) * | 2002-07-29 | 2005-01-06 | Lockwood Samuel Fournier | Carotenoid analogs or derivatives for the inhibition and amelioration of liver disease |
| US7264813B2 (en) | 2003-09-24 | 2007-09-04 | Nikken Sohonsha Corporation | Therapeutic uses of Dunaliella powder |
| EP1716210B1 (en) * | 2004-02-10 | 2016-10-05 | Nestec S.A. | Compositions containing cis-isomers of carotenoids and corresponding method |
| US20060058269A1 (en) * | 2004-04-14 | 2006-03-16 | Lockwood Samuel F | Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation |
| CA2564066A1 (en) * | 2004-04-14 | 2005-11-03 | Hawaii Biotech, Inc. | Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation |
| US7691158B2 (en) * | 2004-06-25 | 2010-04-06 | Oryxe Energy International, Inc. | Hydrocarbon fuel additives and fuel formulations exhibiting improved combustion properties |
| US20060096165A1 (en) * | 2004-06-25 | 2006-05-11 | Oryxe Energy International, Inc. | Novel hydrocarbon fuel additives and fuel formulations exhibiting improved combustion properties |
| WO2006039685A2 (en) | 2004-10-01 | 2006-04-13 | Hawaii Biotech, Inc. | Methods for synthesis of chiral intermediates of carotenoids, carotenoid analogs, and carotenoid derivatives |
| JP2010502572A (ja) * | 2006-08-08 | 2010-01-28 | ネステク ソシエテ アノニム | カロテノイド異性体の安定で生物学的に利用可能な皮膚及び毛髪用組成物 |
| EP2687103B2 (en) * | 2012-07-20 | 2024-07-24 | Basf Se | Process for manufacturing an aqueous transparent oil-in-water emulsion comprising a carotenoid and emulsion produced |
| US20140023712A1 (en) * | 2012-07-20 | 2014-01-23 | Basf Se | Aqueous Transparent Oil-In-Water Emulsion Comprising an Emulsified Carotenoid |
| IL245847A0 (en) | 2016-05-25 | 2016-08-02 | Ramot At Tel-Aviv Univ Ltd | A method for the synthesis of 9-cis-beta-carotene and preparations including it |
| GB201718822D0 (en) | 2017-11-14 | 2017-12-27 | Univ Greenwich | Production of dunaliella |
| GB202114072D0 (en) | 2021-10-01 | 2021-11-17 | Givaudan Sa | Method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3039877A (en) * | 1961-03-02 | 1962-06-19 | Nopco Chem Co | Stabilized carotene compositions |
| US3367985A (en) * | 1966-04-18 | 1968-02-06 | Hoffmann La Roche | Process for the manufacture of polyene compounds |
| US3441623A (en) * | 1967-03-24 | 1969-04-29 | Hoffmann La Roche | Process for the preparation of beta-carotene and intermediates thereof from waste mother liquors |
| US3492202A (en) * | 1967-12-12 | 1970-01-27 | Pfizer & Co C | Process for the production of beta-carotene |
| US3989757A (en) * | 1973-08-29 | 1976-11-02 | Hoffmann-La Roche Inc. | Isomerizing cis-carotenoids to all-trans-carotenoids |
| US4199895A (en) * | 1977-05-25 | 1980-04-29 | Yeda Research And Development Co. Ltd. | Production of glycerol, carotenes and algae meal |
| EP0052777A1 (de) * | 1980-11-20 | 1982-06-02 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Extraktion von beta-Carotin aus Algen |
| US4713398A (en) * | 1985-08-30 | 1987-12-15 | Microbio Resources, Inc. | Naturally-derived carotene/oil composition |
| US4851339A (en) * | 1986-04-01 | 1989-07-25 | Hills Christopher B | Extraction of anti-mutagenic pigments from algae and vegetables |
| US5019668A (en) * | 1988-06-14 | 1991-05-28 | Palm Oil Research & Development Board | Recovery of carotenoids |
| US5206025A (en) * | 1989-05-24 | 1993-04-27 | Rhone-Poulenc Sante | Porous pharmaceutical form and its preparation |
| DE4031094A1 (de) * | 1990-10-02 | 1992-04-09 | Basf Ag | Verfahren zur herstellung von stabilen injizierbaren (beta)-carotin-solubilisaten |
| US5245095A (en) * | 1991-04-12 | 1993-09-14 | Humanetics Corporation | Extraction of carotenoids from natural sources |
| DE4112272A1 (de) * | 1991-04-15 | 1992-10-22 | Basf Ag | 2,5-bis-(1',1'-dialkoxy-2'-propyl)-2,5- dihydrofurane, verfahren zu deren herstellung sowie deren verwendung zur herstellung von carotinoiden |
| US5310554A (en) * | 1992-10-27 | 1994-05-10 | Natural Carotene Corporation | High purity beta-carotene |
-
1993
- 1993-06-04 WO PCT/AU1993/000267 patent/WO1993024454A1/en not_active Ceased
- 1993-06-04 JP JP50003894A patent/JP3547741B2/ja not_active Expired - Fee Related
- 1993-06-04 EP EP93912417A patent/EP0643692B1/en not_active Expired - Lifetime
- 1993-06-04 DE DE69327100T patent/DE69327100T2/de not_active Expired - Fee Related
- 1993-06-04 AT AT93912417T patent/ATE186905T1/de not_active IP Right Cessation
- 1993-06-04 US US08/347,458 patent/US5612485A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69327100T2 (de) | 2000-04-13 |
| US5612485A (en) | 1997-03-18 |
| DE69327100D1 (de) | 1999-12-30 |
| EP0643692A4 (enExample) | 1995-04-05 |
| EP0643692A1 (en) | 1995-03-22 |
| WO1993024454A1 (en) | 1993-12-09 |
| JPH07506837A (ja) | 1995-07-27 |
| EP0643692B1 (en) | 1999-11-24 |
| ATE186905T1 (de) | 1999-12-15 |
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