CN110897165A - Conjugated zinc linoleate preparation and preparation method thereof - Google Patents
Conjugated zinc linoleate preparation and preparation method thereof Download PDFInfo
- Publication number
- CN110897165A CN110897165A CN201911404782.4A CN201911404782A CN110897165A CN 110897165 A CN110897165 A CN 110897165A CN 201911404782 A CN201911404782 A CN 201911404782A CN 110897165 A CN110897165 A CN 110897165A
- Authority
- CN
- China
- Prior art keywords
- zinc
- preparation
- linoleic acid
- conjugated
- conjugated linoleic
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 56
- ODNJVAVDJKOYFK-GRVYQHKQSA-L zinc;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Zn+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O ODNJVAVDJKOYFK-GRVYQHKQSA-L 0.000 title claims abstract description 18
- 229940108924 conjugated linoleic acid Drugs 0.000 claims abstract description 74
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims abstract description 74
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 claims abstract description 73
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000011701 zinc Substances 0.000 claims abstract description 28
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 28
- 150000003751 zinc Chemical class 0.000 claims abstract description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 11
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 239000012266 salt solution Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 239000000243 solution Substances 0.000 claims description 35
- 238000003756 stirring Methods 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 20
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 18
- 239000011592 zinc chloride Substances 0.000 claims description 14
- 235000005074 zinc chloride Nutrition 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- 239000008367 deionised water Substances 0.000 claims description 12
- 229910021641 deionized water Inorganic materials 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 12
- 229960001763 zinc sulfate Drugs 0.000 claims description 12
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 229940102001 zinc bromide Drugs 0.000 claims description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- 239000011591 potassium Substances 0.000 claims description 9
- 239000004246 zinc acetate Substances 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 238000001291 vacuum drying Methods 0.000 claims description 8
- 229960001939 zinc chloride Drugs 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 claims description 7
- -1 conjugated linoleic acid zinc salt Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229960004063 propylene glycol Drugs 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000005714 functional activity Effects 0.000 claims description 2
- 239000013538 functional additive Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000002086 nanomaterial Substances 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 239000008149 soap solution Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 9
- 230000008827 biological function Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- 238000005303 weighing Methods 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 206010048259 Zinc deficiency Diseases 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 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 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 230000001502 supplementing effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 206010006956 Calcium deficiency Diseases 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 206010013883 Dwarfism Diseases 0.000 description 1
- 206010024419 Libido decreased Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010025476 Malabsorption Diseases 0.000 description 1
- 208000004155 Malabsorption Syndromes Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 description 1
- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 206010003883 azoospermia Diseases 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 230000008175 fetal development Effects 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229940070818 glycyrrhizate Drugs 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229940082629 iron antianemic preparations Drugs 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 208000008634 oligospermia Diseases 0.000 description 1
- 230000036616 oligospermia Effects 0.000 description 1
- 231100000528 oligospermia Toxicity 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 230000035938 sexual maturation Effects 0.000 description 1
- WYPBVHPKMJYUEO-NBTZWHCOSA-M sodium;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Na+].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O WYPBVHPKMJYUEO-NBTZWHCOSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- 229960000314 zinc acetate Drugs 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- 239000011670 zinc gluconate Substances 0.000 description 1
- 235000011478 zinc gluconate Nutrition 0.000 description 1
- 229960000306 zinc gluconate Drugs 0.000 description 1
- 239000011576 zinc lactate Substances 0.000 description 1
- 235000000193 zinc lactate Nutrition 0.000 description 1
- 229940050168 zinc lactate Drugs 0.000 description 1
- 229940120347 zinc preparations Drugs 0.000 description 1
Classifications
-
- 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
- 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
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- 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
- 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
- A23L33/16—Inorganic salts, minerals or trace elements
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/30—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Epidemiology (AREA)
- Food Science & Technology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a conjugated linoleic acid zinc preparation and a preparation method thereof. The preparation is prepared from the following raw materials in molar ratio: conjugated linoleic acid: soluble zinc salt 2: 1.00-1.50; the preparation method is that under room temperature or near room temperature, conjugated linoleic acid with biological function activity is firstly saponified with alkali metal alcoholate or alkali metal hydroxide and then reacted with soluble zinc salt solution to obtain conjugated zinc linoleate; the method of the invention is homogeneous reaction, has simple process, simple and convenient operation, high product purity and stable property, and is particularly suitable for the application field with higher requirements on product quality.
Description
Technical Field
The invention relates to the technical field of nutrition supplementing preparations, in particular to a conjugated zinc linoleate preparation and a preparation method thereof.
Background
Conjugated linoleic acid was discovered in the end of the 80's 20 th century as a natural fatty acid with many important biological activities. Animal experiments show that the conjugated linoleic acid has the functions of reducing fat, increasing muscle, resisting cancer and atherosclerosis, enhancing the immunity of the body, improving the metabolism of bone tissues and the like. Conjugated linoleic acid, as a newly discovered nutrient, does not have the so-called homology problem because it is a secondary metabolite of animals, does not have the upper limit problem of use in principle, and is beneficial and harmless to the body when being frequently eaten. The conjugated linoleic acid with a certain dosage is added into the food, so that the deficiency of human body intake can be made up, the capability of resisting a plurality of diseases of the human body can be enhanced, and the immunity of the human body can be improved. At present, conjugated linoleic acid has become one of the research hotspots in the fields of medicines, functional foods and the like, and has been developed into health care products for reducing human body fat and increasing muscles abroad, and some capsule preparation products are put on the market, but the comprehensive development and deep processing utilization of the conjugated linoleic acid at home are blank, the raw materials of the products are easy to obtain, and the market prospect is wide.
Chinese patent CN1357406A discloses a microcapsule of conjugated linoleic acid. The product is composed of conjugated linoleic acid salt, other fatty acid salt, wall material, solvent and antioxidant, but the conjugated linoleic acid is difficult to be completely converted, and free conjugated linoleic acid or unreacted free alkali can be mixed in the product, so that the product is impure, and the quality stability of the product is influenced.
According to the research report of the Chinese disease prevention and control center nutrition and food safety institute, the zinc element is an indispensable trace element for human bodies and plays a vital role in life bodies. It is known that zinc is a component of more than 100 enzymes in the human body, and related biological enzymes play an important role in tissue respiration and metabolism of proteins, fats, sugars, nucleic acids, and the like; zinc deficiency can cause dwarfism, difficulty in healing of damaged tissues and influence on fetal development; can cause slow taste, anorexia, sexual maturation retardation, sexual organ hypoplasia, sexual hypofunction, hyposexuality, oligospermia, and abnormal menstruation; the zinc deficiency can cause the reduction of the proliferation of immune cells, the reduction of the activity of thymus and the change of cell surface receptors. In addition, zinc is helpful for removing cholesterol in vivo, preventing and treating atherosclerosis, and inhibiting canceration of cells. The causes of zinc deficiency can be summarized as congenital poor storage, intake deficiency and malabsorption. The zinc deficiency of the adolescent children is particularly common because the human body needs a large amount of zinc. Therefore, scientifically and effectively maintaining the zinc element balance of the human body is of great importance to the life body.
Inorganic zinc and small molecular organic zinc preparations in the current market have poor effect as food and drug supplement preparations, stimulate intestines and stomach, produce related side effects, and further need to improve quality and upgrade for generations. The absorption and utilization rate of inorganic zinc (zinc sulfate, zinc chloride, zinc nitrate and the like) is low (only 7%), and the gastrointestinal tract is easily stimulated to cause adverse reaction; the organic acid zinc (zinc gluconate, zinc glycyrrhizate, zinc acetate, zinc citrate, zinc amino acid, zinc lactate, etc.) has high zinc content, and can inhibit absorption of other microelements such as calcium and iron, and can cause calcium deficiency and anemia.
The bioaffinity zinc is the multifunctional conjugated zinc linoleate developed by the patent, has low zinc content which is almost equivalent to the zinc content of food, is absolutely safe, has no side effect on human bodies, and can be taken before meals. The food has high activity, can effectively promote the absorption and utilization of various nutrients by a human body, and can not antagonize the absorption of the nutrients such as calcium, iron and the like, thereby finally achieving the effect of supplementing various nutrients from diet of the human body. The biological affinity zinc, pure biological agent, high activity, easy absorption and quick effect. And is safe without any hormone and toxic and side effects, thereby being very beneficial to the absorption of calcium and other trace elements. After the zinc is biologically functionalized, the oxidation stability of the conjugated linoleic acid is improved, the stability and the usability are enhanced, and the functionality is increased. The composite high-grade nutriment, namely the conjugated linoleic acid is a novel multifunctional high-grade nutriment and can also be used as an important component preparation of food and medicines.
Disclosure of Invention
The invention aims to solve the technical problems and provide a conjugated zinc linoleate preparation with high product purity and stable product quality and a preparation method thereof.
In order to solve the technical problems, the technical scheme provided by the invention is as follows: a conjugated zinc linoleate preparation is prepared from the following raw materials in molar ratio: conjugated linoleic acid: soluble zinc salt 2: 1.00-1.50;
the conjugated linoleic acid zinc preparation is prepared by the steps of firstly saponifying a pure product of conjugated linoleic acid with biological functional activity with alkali metal alcoholate or alkali metal hydroxide at room temperature or near room temperature, and then reacting with soluble zinc salt.
As an improvement, the conjugated linoleic acid is a pure product of the conjugated linoleic acid or a mixed fatty acid of the conjugated linoleic acid.
As a refinement, the alkali metal is lithium, potassium or sodium; the alcohol solution is any one or any two or any three of methanol, ethanol, ethylene glycol, propanol, isopropanol, 1, 2-propylene glycol, 1, 3-propylene glycol and glycerol or a mixture of any two or any three of the above and water.
The soluble zinc salt is any one of zinc chloride, zinc bromide, zinc sulfate, zinc nitrate or zinc acetate, or a mixture of two or three of zinc chloride, zinc bromide, zinc sulfate, zinc nitrate or zinc acetate.
A preparation method of a conjugated zinc oleate preparation comprises the following operation steps:
(1) adding aqueous solution or alcoholic solution of alkali metal hydroxide or alkali metal alcoholate into conjugated linoleic acid with equivalent weight under the protection of inert gas at room temperature or near room temperature, and stirring for reaction for 1-6 hours to obtain alkali metal soap solution of conjugated linoleic acid;
(2) adding an equivalent amount of soluble zinc salt solution into the solution generated in the step (1), stirring until solid is separated out, clarifying a liquid part, carrying out centrifugal separation, and removing clear liquid to obtain crude conjugated linoleic acid zinc salt;
(3) washing the crude conjugated zinc linoleate with deionized water and low molecular alcohol or ether, and vacuum drying at 20-90 deg.c to obtain the conjugated zinc linoleate preparation.
As an improvement, the conjugated linoleic acid is a pure product of the conjugated linoleic acid or a mixed fatty acid of the conjugated linoleic acid.
As a refinement, the alkali metal is lithium, potassium or sodium; the alcohol solution is any one or any two or any three of methanol, ethanol, ethylene glycol, propanol, isopropanol, 1, 2-propylene glycol, 1, 3-propylene glycol and glycerol or a mixture of any two or any three of the above and water.
The improvement is that the soluble zinc salt is any one of zinc chloride, zinc bromide, zinc sulfate, zinc nitrate and zinc acetate, or a mixture of two or three of zinc chloride, zinc bromide, zinc sulfate, zinc nitrate and zinc acetate.
As an improvement, the content of the synthesized conjugated linoleic acid zinc is consistent with that of the conjugated linoleic acid in the raw material, and the other components are zinc salts of the rest fatty acids contained in the raw material.
As an improvement, the conjugated zinc linoleate is used as a functional additive of nutriments, a medicinal component and a precursor of a nano material.
Compared with the prior art, the invention has the advantages that: the reaction is uniform, the product purity is high, the product quality is stable, and the method is particularly suitable for the field of biotechnology with high requirements on the product quality.
Detailed Description
The content of calcium and magnesium in the conjugated linoleic acid composite preparation is measured by a plasma emission spectrometer Perkin-Elmer Optima 7300V ICP. The conjugated linoleic acid content in the conjugated linoleic acid compound preparation is determined by a liquid chromatograph Agilent InfinityLab LC/MSD. The conjugated linoleic acid is mixed fatty acid and comprises the following components in percentage by weight: the Conjugated Linoleic Acid (CLA) was 85.18%, and the other fatty acids (including linoleic acid, oleic acid, stearic acid, etc.) were 14.82%.
Example one
(1) Weighing 30g of conjugated linoleic acid in 450ml of distilled water at the room temperature of 25 ℃ under the protection of nitrogen, adding 45ml of 10 wt% sodium hydroxide solution under stirring, and stirring for 2 hours to obtain a conjugated sodium linoleate solution;
(2) adding 106ml of 10 wt% zinc chloride solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated zinc linoleate preparation;
(3) washing the crude preparation with distilled water, deionized water and methanol in sequence, vacuum drying at 60 ℃, and crushing to obtain 30.6g of a product.
Example two
(1) Weighing 30g of conjugated linoleic acid in 300ml of distilled water at the temperature of 30 ℃ near room temperature under the protection of nitrogen, adding 42ml of 10 wt% sodium hydroxide solution under stirring, and stirring for 4 hours to obtain a sodium solution of the conjugated linoleic acid;
(2) adding 160ml of 10 wt% zinc bromide solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated zinc linoleate preparation;
(3) washing the crude preparation with distilled water, deionized water and diethyl ether in sequence, vacuum drying at 50 ℃, and crushing to obtain 30.18g of a product.
EXAMPLE III
(1) Weighing 30g of conjugated linoleic acid in 300ml of methanol at the temperature of 35 ℃ near room temperature under the protection of nitrogen, adding 48ml of 10 wt% potassium hydroxide solution under stirring, and stirring for 4 hours to obtain a potassium solution of the conjugated linoleic acid;
(2) adding 180ml of 10 wt% zinc sulfate solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated zinc linoleate preparation;
(3) washing the crude preparation with distilled water, deionized water and methanol in sequence, vacuum drying at 80 ℃, and crushing to obtain 30.68g of a product.
Example four
(1) Weighing 30g of conjugated linoleic acid in 400ml of propanol at the temperature of 45 ℃ near room temperature under the protection of nitrogen, adding 45ml of 10 wt% potassium hydroxide solution under stirring, and stirring for 2.5 hours to obtain a potassium solution of the conjugated linoleic acid;
(2) adding 165ml of 10 wt% zinc sulfate solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated linoleic acid zinc preparation;
(3) washing the crude preparation with distilled water, deionized water and methanol in sequence, drying in vacuum at 60 ℃, and crushing to obtain 33.18g of a product.
EXAMPLE five
(1) Weighing 30g of conjugated linoleic acid in 408ml of propanol at the room temperature of 25 ℃ under the protection of argon, adding 31ml of 10 wt% potassium hydroxide solution under stirring, and stirring for 5 hours to obtain a potassium solution of the conjugated linoleic acid;
(2) adding 165ml of 10 wt% zinc sulfate solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated linoleic acid zinc preparation;
(3) washing the crude preparation with distilled water, deionized water and ethanol in sequence, drying in vacuum at 75 ℃, and crushing to obtain 30.81g of a product.
EXAMPLE six
(1) Weighing 30g of conjugated linoleic acid in 541ml of methanol at room temperature of 25 ℃ under the protection of argon, adding 33ml of 10 wt% potassium hydroxide solution under stirring, and stirring for 5 hours to obtain a potassium solution of the conjugated linoleic acid;
(2) adding 165ml of 10 wt% zinc chloride solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated linoleic acid zinc preparation;
(3) washing the crude preparation with distilled water, deionized water and ethanol in sequence, vacuum drying at 80 ℃, and crushing to obtain 32.18g of a product.
EXAMPLE seven
(1) Weighing 30g of conjugated linoleic acid in 540ml of methanol at the room temperature of 25 ℃ under the protection of argon, adding 48ml of 10 wt% potassium hydroxide solution under stirring, and stirring for 6 hours to obtain a potassium solution of the conjugated linoleic acid;
(2) adding 180ml of 10 wt% zinc chloride solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated linoleic acid zinc preparation;
(3) washing the crude preparation with distilled water, deionized water and methanol in sequence, drying in vacuum at 85 ℃, and crushing to obtain 33.86g of a product.
Example eight
(1) Weighing 30g of conjugated linoleic acid in 455ml of methanol at a temperature close to 36 ℃ under the protection of argon, adding 48ml of 10 wt% sodium hydroxide solution under stirring, and stirring for 5 hours to obtain a sodium solution of the conjugated linoleic acid;
(2) adding 153ml of 10 wt% zinc solution (the molar ratio of zinc chloride to zinc bromide is 1: 1) while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated linoleic acid zinc preparation;
(3) washing the crude preparation with distilled water, deionized water and propanol in sequence, vacuum drying at 65 ℃, and crushing to obtain 31.8g of a product.
Example nine
(1) 20g of conjugated linoleic acid is weighed in 255ml of alcoholic solution (methanol and ethanol) at the temperature of nearly 40 ℃ under the protection of nitrogen
The volume ratio of the alcohol is 2: 1) adding 24ml of 10 wt% sodium hydroxide solution while stirring, and stirring for 3 hours to obtain a sodium solution of conjugated linoleic acid;
(2) adding 90ml of 10 wt% ferrous chloride solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated linoleic acid zinc preparation;
(3) washing the crude preparation with distilled water, deionized water and diethyl ether in sequence, vacuum drying at 55 ℃, and crushing to obtain 16.8g of a product.
Example ten
(1) Weighing 20g of conjugated linoleic acid in 285ml of alcoholic solution (the volume ratio of methanol to water is 2: 1) at the temperature of 8 ℃ near room temperature under the protection of nitrogen, adding 30ml of 10 percent wt sodium hydroxide solution under stirring, and stirring for 6 hours to obtain sodium solution of the conjugated linoleic acid;
(2) adding 88ml of 10 wt% zinc chloride solution while stirring to form a light yellow granular substance, and performing centrifugal separation to obtain a crude conjugated zinc linoleate preparation;
(3) washing the crude preparation with distilled water, deionized water and ethanol in sequence, drying in vacuum at 25 ℃, and crushing to obtain 18.16g of a product.
TABLE 1 component content of the conjugated linoleic acid iron preparations prepared in the examples of the present invention
Claims (10)
1. The conjugated zinc linoleate preparation is characterized by being prepared from the following raw materials in molar ratio: conjugated linoleic acid: soluble zinc salt 2: 1.00-1.50;
the conjugated linoleic acid zinc preparation is prepared by the steps of firstly saponifying a pure product of conjugated linoleic acid with biological functional activity with alkali metal alcoholate or alkali metal hydroxide at room temperature or near room temperature, and then reacting with soluble zinc salt.
2. The preparation of claim 1, wherein the conjugated linoleic acid is a pure product of conjugated linoleic acid or a mixed fatty acid of conjugated linoleic acid.
3. The preparation of claim 1, wherein the alkali metal is lithium, potassium or sodium; the alcohol solution is any one or any two or any three of methanol, ethanol, ethylene glycol, propanol, isopropanol, 1, 2-propylene glycol, 1, 3-propylene glycol and glycerol or a mixture of any two or any three of the above and water.
4. The preparation of claim 1, wherein the soluble zinc salt is any one of zinc chloride, zinc bromide, zinc sulfate, zinc nitrate, and zinc acetate, or a mixture of two or three of zinc chloride, zinc bromide, zinc sulfate, zinc nitrate, and zinc acetate.
5. The preparation method of the conjugated zinc oleate preparation is characterized by comprising the following operation steps:
(1) adding aqueous solution or alcoholic solution of alkali metal hydroxide or alkali metal alcoholate into conjugated linoleic acid with equivalent weight under the protection of inert gas at room temperature or near room temperature, and stirring for reaction for 1-6 hours to obtain alkali metal soap solution of conjugated linoleic acid;
(2) adding an equivalent amount of soluble zinc salt solution into the solution generated in the step (1), stirring until solid is separated out, clarifying a liquid part, carrying out centrifugal separation, and removing clear liquid to obtain crude conjugated linoleic acid zinc salt;
(3) washing the crude conjugated zinc linoleate with deionized water and low molecular alcohol or ether, and vacuum drying at 20-90 deg.c to obtain the conjugated zinc linoleate preparation.
6. The method of claim 5, wherein the preparation of the conjugated zinc oleate is prepared by the following steps: the conjugated linoleic acid is a pure product of the conjugated linoleic acid or a mixed fatty acid of the conjugated linoleic acid.
7. The method of claim 5, wherein the preparation of the conjugated zinc oleate is prepared by the following steps: the alkali metal is lithium, potassium or sodium; the alcohol solution is any one or any two or any three of methanol, ethanol, ethylene glycol, propanol, isopropanol, 1, 2-propylene glycol, 1, 3-propylene glycol and glycerol or a mixture of any two or any three of the above and water.
8. The method of claim 5, wherein the preparation of the conjugated zinc oleate is prepared by the following steps: the soluble zinc salt is any one of zinc chloride or zinc bromide or zinc sulfate or zinc nitrate or zinc acetate, or a mixture of two or three of zinc chloride or zinc bromide or zinc sulfate or zinc nitrate or zinc acetate.
9. The method of claim 5, wherein the preparation of the conjugated zinc oleate is prepared by the following steps: the content of the synthesized conjugated linoleic acid zinc is consistent with that of the conjugated linoleic acid in the raw material, and the other components are zinc salts of the rest fatty acids in the raw material.
10. The method of claim 5, wherein the preparation of the conjugated zinc oleate is prepared by the following steps: the conjugated zinc linoleate is used as a functional additive of nutriments, a medicinal component and a precursor of a nano material.
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| CN101849933A (en) * | 2010-04-15 | 2010-10-06 | 广东海洋大学 | Conjugated linoleic acid ferrite preparation and preparation method thereof |
| CN101849932A (en) * | 2010-04-15 | 2010-10-06 | 广东海洋大学 | Nutrient preparation of iron and zinc and preparation method thereof |
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