GB1064645A - Production in pure form of compounds of the carotenoid and vitamin-a series - Google Patents
Production in pure form of compounds of the carotenoid and vitamin-a seriesInfo
- Publication number
- GB1064645A GB1064645A GB28515/64A GB2851564A GB1064645A GB 1064645 A GB1064645 A GB 1064645A GB 28515/64 A GB28515/64 A GB 28515/64A GB 2851564 A GB2851564 A GB 2851564A GB 1064645 A GB1064645 A GB 1064645A
- Authority
- GB
- United Kingdom
- Prior art keywords
- water
- vitamin
- polyoxyethylated
- acid
- purified
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 5
- 235000021466 carotenoid Nutrition 0.000 title abstract 4
- 150000001747 carotenoids Chemical class 0.000 title abstract 4
- 229940045997 vitamin a Drugs 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 10
- 239000004094 surface-active agent Substances 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 4
- 159000000000 sodium salts Chemical class 0.000 abstract 4
- -1 polyoxyethylene Polymers 0.000 abstract 3
- LPMBTLLQQJBUOO-KTKRTIGZSA-N (z)-n,n-bis(2-hydroxyethyl)octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(CCO)CCO LPMBTLLQQJBUOO-KTKRTIGZSA-N 0.000 abstract 2
- KYZKCQBBHSPHOB-UHFFFAOYSA-M 1-dodecyl-1-methylimidazol-1-ium methyl sulfate Chemical compound S(=O)(=O)(OC)[O-].C(CCCCCCCCCCC)[N+]1(C=NC=C1)C KYZKCQBBHSPHOB-UHFFFAOYSA-M 0.000 abstract 2
- KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 abstract 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 2
- 229920001214 Polysorbate 60 Polymers 0.000 abstract 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 abstract 2
- 239000003963 antioxidant agent Substances 0.000 abstract 2
- 230000003078 antioxidant effect Effects 0.000 abstract 2
- 235000006708 antioxidants Nutrition 0.000 abstract 2
- IDMGVRDNZFQORW-JWBAUCAFSA-N axerophthene Chemical compound C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C IDMGVRDNZFQORW-JWBAUCAFSA-N 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 235000019438 castor oil Nutrition 0.000 abstract 2
- 239000003240 coconut oil Substances 0.000 abstract 2
- 235000019864 coconut oil Nutrition 0.000 abstract 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Polymers C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- 238000005406 washing Methods 0.000 abstract 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Polymers CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 abstract 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 abstract 1
- VJWGHGJYLCJIEK-UHFFFAOYSA-N 1,4-bis(6-methylheptoxy)-1,4-dioxobutane-2-sulfonic acid Chemical compound CC(C)CCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCC(C)C VJWGHGJYLCJIEK-UHFFFAOYSA-N 0.000 abstract 1
- GNPSDJOWGWWXSS-UHFFFAOYSA-M 1-benzylpyridin-1-ium;chloride Chemical compound [Cl-].C=1C=CC=C[N+]=1CC1=CC=CC=C1 GNPSDJOWGWWXSS-UHFFFAOYSA-M 0.000 abstract 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 abstract 1
- PWFBXQPPJCAUMR-UHFFFAOYSA-N 2,4,6-trimethyl-4-octadecylmorpholin-4-ium Chemical compound CC1C[N+](CC(O1)C)(CCCCCCCCCCCCCCCCCC)C PWFBXQPPJCAUMR-UHFFFAOYSA-N 0.000 abstract 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Polymers CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 abstract 1
- FVIMRJIDRHUTQP-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCN(CCO)CCO FVIMRJIDRHUTQP-UHFFFAOYSA-N 0.000 abstract 1
- HEBVQLXISFQBCP-UHFFFAOYSA-N C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1.CN(C1=CC=CC=C1)C Chemical compound C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1.CN(C1=CC=CC=C1)C HEBVQLXISFQBCP-UHFFFAOYSA-N 0.000 abstract 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 abstract 1
- NCYCYZXNIZJOKI-OVSJKPMPSA-N Retinaldehyde Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 abstract 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 abstract 1
- 235000019169 all-trans-retinol Nutrition 0.000 abstract 1
- 239000011717 all-trans-retinol Substances 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 abstract 1
- 229960001484 edetic acid Drugs 0.000 abstract 1
- 150000002191 fatty alcohols Chemical class 0.000 abstract 1
- 229940070765 laurate Drugs 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- 235000020945 retinal Nutrition 0.000 abstract 1
- 239000011604 retinal Substances 0.000 abstract 1
- 229930002330 retinoic acid Natural products 0.000 abstract 1
- 229960000342 retinol acetate Drugs 0.000 abstract 1
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 abstract 1
- 235000019173 retinyl acetate Nutrition 0.000 abstract 1
- 239000011770 retinyl acetate Substances 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 229950004959 sorbitan oleate Drugs 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- 150000002266 vitamin A derivatives Chemical class 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
Classifications
-
- 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
- C07F9/54—Quaternary phosphonium compounds
-
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- 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
- C07C403/02—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 containing only carbon and hydrogen atoms
-
- 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
- C07C403/06—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 singly-bound oxygen atoms
- C07C403/08—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 singly-bound oxygen atoms by hydroxy groups
-
- 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
- C07C403/06—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 singly-bound oxygen atoms
- C07C403/12—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 singly-bound oxygen atoms by esterified hydroxy groups
-
- 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
- C07C403/14—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 doubly-bound oxygen atoms
-
- 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
- C07C403/20—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 carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB72746A DE1199258B (de) | 1963-07-19 | 1963-07-19 | Verfahren zur Reindarstellung von Verbindungen der Carotinoid- und Vitamin A-Reihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1064645A true GB1064645A (en) | 1967-04-05 |
Family
ID=6977573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28515/64A Expired GB1064645A (en) | 1963-07-19 | 1964-07-10 | Production in pure form of compounds of the carotenoid and vitamin-a series |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3356753A (https=) |
| CH (1) | CH433269A (https=) |
| DE (1) | DE1199258B (https=) |
| GB (1) | GB1064645A (https=) |
| NL (2) | NL6408209A (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998003480A1 (en) * | 1996-07-19 | 1998-01-29 | Gist-Brocade B.V. | PROCESS FOR THE RECOVERY OF CRYSTALLINE β-CAROTENE FROM A NATURAL SOURCE |
| WO1998050574A1 (en) * | 1997-05-02 | 1998-11-12 | Dsm N.V. | Isolation of carotenoid crystals from microbial biomass |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6606913A (https=) * | 1966-05-19 | 1967-11-20 | ||
| US4962275A (en) * | 1990-02-21 | 1990-10-09 | United States Of America As Represented By The Secretary Of Commerce | Method and apparatus for supercritical fluid extraction solution separation |
-
0
- NL NL126583D patent/NL126583C/xx active
-
1963
- 1963-07-19 DE DEB72746A patent/DE1199258B/de active Pending
-
1964
- 1964-06-18 CH CH799064A patent/CH433269A/de unknown
- 1964-07-06 US US380656A patent/US3356753A/en not_active Expired - Lifetime
- 1964-07-10 GB GB28515/64A patent/GB1064645A/en not_active Expired
- 1964-07-17 NL NL6408209A patent/NL6408209A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998003480A1 (en) * | 1996-07-19 | 1998-01-29 | Gist-Brocade B.V. | PROCESS FOR THE RECOVERY OF CRYSTALLINE β-CAROTENE FROM A NATURAL SOURCE |
| WO1998050574A1 (en) * | 1997-05-02 | 1998-11-12 | Dsm N.V. | Isolation of carotenoid crystals from microbial biomass |
| US6812001B2 (en) | 1997-05-02 | 2004-11-02 | Dsm N.V. | Isolation of carotenoid crystals from microbial biomass |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6408209A (https=) | 1965-01-20 |
| NL126583C (https=) | |
| CH433269A (de) | 1967-04-15 |
| US3356753A (en) | 1967-12-05 |
| DE1199258B (de) | 1965-08-26 |
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