CN106135904A - A kind of diglyceride fluid composition rich in calendic acid and its preparation method and application - Google Patents
A kind of diglyceride fluid composition rich in calendic acid and its preparation method and application Download PDFInfo
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- CN106135904A CN106135904A CN201510148852.XA CN201510148852A CN106135904A CN 106135904 A CN106135904 A CN 106135904A CN 201510148852 A CN201510148852 A CN 201510148852A CN 106135904 A CN106135904 A CN 106135904A
- Authority
- CN
- China
- Prior art keywords
- diglyceride
- calendic acid
- acid
- fluid composition
- calendic
- Prior art date
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- DQGMPXYVZZCNDQ-UVZPLDOLSA-N Calendinsaeure Natural products CCCCCC=C/C=C/C=C/CCCCCCC(=O)O DQGMPXYVZZCNDQ-UVZPLDOLSA-N 0.000 title claims abstract description 122
- DQGMPXYVZZCNDQ-KBPWROHVSA-N (8E,10E,12Z)-octadecatrienoic acid Chemical compound CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O DQGMPXYVZZCNDQ-KBPWROHVSA-N 0.000 title claims abstract description 121
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 239000012530 fluid Substances 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 61
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 52
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 24
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 22
- 239000000194 fatty acid Substances 0.000 claims abstract description 22
- 229930195729 fatty acid Natural products 0.000 claims abstract description 22
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000037396 body weight Effects 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 8
- 235000013376 functional food Nutrition 0.000 claims abstract description 8
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 7
- 230000036039 immunity Effects 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- 238000002425 crystallisation Methods 0.000 claims description 28
- 230000008025 crystallization Effects 0.000 claims description 24
- 239000000287 crude extract Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000003208 petroleum Substances 0.000 claims description 16
- 108010048733 Lipozyme Proteins 0.000 claims description 13
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 12
- 238000007127 saponification reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 241000628997 Flos Species 0.000 claims description 8
- 238000006555 catalytic reaction Methods 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000005194 fractionation Methods 0.000 claims description 6
- 238000000199 molecular distillation Methods 0.000 claims description 6
- 230000004044 response Effects 0.000 claims description 6
- 230000008014 freezing Effects 0.000 claims description 5
- 238000007710 freezing Methods 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000000194 supercritical-fluid extraction Methods 0.000 claims description 4
- -1 calendic acid ester Chemical class 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000003825 pressing Methods 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- CGKQZIULZRXRRJ-UHFFFAOYSA-N Butylone Chemical compound CCC(NC)C(=O)C1=CC=C2OCOC2=C1 CGKQZIULZRXRRJ-UHFFFAOYSA-N 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 239000008280 blood Substances 0.000 abstract description 6
- 210000004369 blood Anatomy 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 239000000243 solution Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 241000699666 Mus <mouse, genus> Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 6
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 229960004488 linolenic acid Drugs 0.000 description 6
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 5
- 102000004882 Lipase Human genes 0.000 description 5
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 description 4
- 239000004367 Lipase Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000030538 Thecla Species 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 4
- 235000019421 lipase Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241001111310 Calycocarpum lyonii Species 0.000 description 3
- 108010084311 Novozyme 435 Proteins 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- 229940108924 conjugated linoleic acid Drugs 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 108060003951 Immunoglobulin Proteins 0.000 description 2
- 210000000577 adipose tissue Anatomy 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000008901 benefit 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
- 230000021615 conjugation Effects 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 238000003304 gavage Methods 0.000 description 2
- 230000036737 immune function Effects 0.000 description 2
- 102000018358 immunoglobulin Human genes 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000000582 semen Anatomy 0.000 description 2
- 125000005457 triglyceride group Chemical group 0.000 description 2
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-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
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 240000001432 Calendula officinalis Species 0.000 description 1
- 235000005881 Calendula officinalis Nutrition 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 208000001145 Metabolic Syndrome Diseases 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001924 fatty-acyl group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000005672 tetraenes Chemical class 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/02—Pretreatment
- C11B1/04—Pretreatment of vegetable raw material
-
- 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
- A61K31/202—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 three or more double bonds, e.g. linolenic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/06—Production of fats or fatty oils from raw materials by pressing
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
- C11B1/104—Production of fats or fatty oils from raw materials by extracting using super critical gases or vapours
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention relates to a kind of diglyceride fluid composition rich in calendic acid, this diglyceride fluid composition is made up of following components by mass percentage: 50～the monoglyceride of the triglyceride of the diglyceride of 85%, 8～35%, 0.3～10% and 0.05～the residue of 10%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, calendic acid is 0.3～0.9:1 with the mass ratio of fatty acid, and described residue is free fatty and glycerol；Further relate to the preparation method of said composition and controlling body weight, the application improved in blood fat and the functional food of raising immunity and medicine.The diglyceride fluid composition rich in calendic acid in the present invention had both had the effect of weight reducing of diglyceride, also there is the effects such as the antiinflammatory of calendic acid, fat-reducing simultaneously, so that said composition can be widely used in control body weight, improve in blood fat and the functional food of raising immunity and medicine, in a word, the preparation technology of said composition is simple, low cost, has broad application prospects.
Description
Technical field
The present invention relates to applied chemistry technical field, particularly relate to a kind of diglyceride fluid composition rich in calendic acid and its preparation method and application.
Background technology
Diglyceride (Diacylglycerol) is the structured lipid that in a quasi-glycerol three-ester (Triacylglycerol), a fatty acid is optionally substituted by a hydroxyl group, it is micro constitutent and the endogenous centre of body fat metabolism of natural plant grease, it has two kinds of natural isomerss, i.e. 1,2-diglyceride and 1,3-diglyceride, as shown in Equation 1.
Formula 1 diglyceride structural representation (wherein COR, COR ' be saturated or unsaturated fatty acyl group)
7 kinds of article such as at present, finding through multinomial safety evaluation, diglyceride is harmless to human non-toxic, is regarded as " It is generally accepted safety " material by U.S. FDA, No. 18 bulletin approval triglyceride oil of ministry of Health of China in 2009 are new resource food.Although diglyceride and triglyceride can be worth and on absorbance essentially identical, but there is larger difference in they metabolism in vivo, short-term and long-term animal and human trial show, compared with the triglyceride formed containing same or similar fatty acid, 1,3-DAG has control and treats high blood triglyceride disease, obesity and the effect of complication thereof.Therefore, the edible oil rich in 1,3-DAG is possible not only to the oil for health care substituting triglyceride edible oil as healthy population, it is also possible to for obese people and the nutrition treatment of related complication crowd.
At present, the preparation method of diglyceride mainly has following several: (1) triglyceride alcoholysis method: i.e. under the catalysis of lipase, triglyceride reacts with lower alcohol, generate diglyceride and low-carbon-ester, but lipase the Novozyme 435 and Lipozyme IM that the method uses can only specific cleavage or synthesis sn-1 position or the ester bond of sn-3 position, therefore can only obtain 1,2-diglyceride.(2) partial hydrolysis, esterification process: i.e. first partial hydrolysis triglyceride obtains fatty acid, add glycerol, under the catalysis of sn-1 and sn-3 position selected fat enzyme, the fatty acid generation esterification that glycerol and partial hydrolysis obtain generates 1, 3-diglyceride, current most diglyceride includes that the EnovaTM Oil that KAO. Corp. SA produces develops based on this principle, the shortcoming of the method maximum is that technological process is complicated, multistep is needed to separate, in addition the utilization rate of raw material is low, additionally need use lipase, and lipase price is higher, there is the problems such as high cost for industrial scale produces diglyceride.(3) glycerol solution: will triglyceride oil and glycerol and a kind of mix containing monocarboxylic acid or the alkali metal salt of dicarboxylic acids or alkali salt or its mixture (making catalyst), by the glycerolysis of triglyceride, prepare business, food stage 1,3-triglyceride oil, but conventional glycerol rhizolomy needs to react under the high temperature of 220～260 DEG C so that the Oxidation of triglyceride, diglyceride and fatty acid particularly unsaturated fatty acid strengthens.At present, prepare triglyceride oil to be mainly by triglyceride type oil and fat preparations such as soybean oil, Oleum Brassicae campestris, Oleum Arachidis hypogaeae semen and Semen Maydis oil, prepare diglyceride with fish oil etc. for raw material and the most also have a small amount of report, as (2010) such as Feltes prepare the diglyceride rich in n-3PUFA with lipase Novozyme 435 by triglyceride alcoholysis method；Eoma etc. (2010) synthesize the diglyceride rich in n-3PUFA with lipase RMIM and Novozyme 435 by hydrolysis, esterification process.
Conjugated fatty acid is to polyunsaturated fatty acid position and the common name of stereoisomer with conjugate double bond system, if there being a methyl between two double bonds, we can be referred to as the double bond that methyl separates, if there being multiple methyl, we term it the double bond that many methyl separate, if two double bond conjugated are together, we term it conjugated fatty acid.Conjugated fatty acid can be with the form being diene, triolefin or tetraene, the most common conjugated fatty acid is octadecadienoic acid and jeceric acid, namely conjugated linoleic acid (Conjugated linoleic acid, and conjugate linolenic acid (Conjugated linolenic acid, CLNA) CLA).Conjugate linolenic acid is different with configuration and have multiple isomer due to position of double bond, trans 8, trans10, cis12-conjugate linolenic acid (cis8, trans10, cis12-18:3) it is 8,10,12 double bonds conjugation, 8 and 12 double bonds are configured as trans, 12 double bonds are configured as trans conjugate linolenic acid (trans8, trans10, cis12-CLNA), domestic also trans8, trans10, cis12-conjugate linolenic acid is referred to as calendic acid (alpha-Calendic acid).Calendic acid can be the most isolated and purified and obtain from plant Flos Inulae (Calendula officinalis) seed seed, calendic acid and trans10, cis12-CLA (10,12 double bond conjugation, 12 double bonds are configured as cis, 10 double bonds are configured as trans, the most important a kind of isomer of conjugated linoleic acid) similarity be that their fatty acid chain the 10th and the 12nd is all undersaturated double bond, and spatial configuration is identical.Calendic acid can be converted to trans10, cis12-CLA in animal and human body, therefore can be as trans10, natural diets source important for cis12-CLA.
Conjugated fatty acid has the special physiological function different from conventional polyunsaturated fatty acid.It is reported, CLA has the most favourable physiological function, as improved humans and animals blood fat, atherosclerosis, obesity, anticancer and antihypertensive effect (Rainer etc., 2004).CLA is in the whole world, and particularly American-European countries is used widely as the functional food such as fat-reducing, blood fat reducing and health product, and it is the main isomer that CLA plays effect of weight reducing that research has proven to trans10, cis12-CLA.CLA is primarily present in milk lipid, cheese and ruminant meat.But, CLA content in these foods only has about 1% (Sehat etc., 1998), and this makes it can not make the sanatory food containing CLA or medicine with the CLA that natural resources exists.The CLA of commercial is that this isomerization product generally comprises equimolar cis9, trans11-CLA and trans10, cis12-CLA (Pariza etc., 2001) and other isomers by the oily isomerization rich in oleic acid is obtained.There is the consideration of the aspects such as safety to the CLA of preparation of industrialization in consumer, CLA industrialized production Costco Wholesale is higher, and the CLA of preparation of industrialization has various isomeric forms, and is not that every kind of isomer all has the function useful to human body.
Calendic acid and trans10, the crucial difference of cis12-CLA is the 3rd undersaturated double bond of calendic acid, and calendic acid has a cis double bond, so calendic acid has again the feature of " polyunsaturated fatty acid " the 8th of fatty acid chain.Polyunsaturated fatty acid has important nutritive value, and triglyceride and cholesterol in humans and animals body are had useful effect, can reduce the danger of cardiovascular and cerebrovascular disease, promotes g and D.At present, polyunsaturated fatty acid is widely used in the development adding growth promoter and the intelligence promoting baby in baby food to.Research finds that calendic acid has anticancer, prevents and treats the metabolic syndromes such as obesity, improving the functions such as immunity.
Summary of the invention
First to be solved by this invention technical problem is that and provide a kind of diglyceride fluid composition rich in calendic acid for prior art.
Second to be solved by this invention technical problem is that the preparation method providing a kind of above-mentioned diglyceride fluid composition rich in calendic acid for prior art.
3rd to be solved by this invention technical problem is that the application providing a kind of above-mentioned diglyceride fluid composition rich in calendic acid for prior art.
The present invention solves the technical scheme that first technical problem used: a kind of diglyceride fluid composition rich in calendic acid, it is characterized in that, this diglyceride fluid composition is made up of following components by mass percentage: 50～the monoglyceride of the triglyceride of the diglyceride of 85%, 8～35%, 0.3～10% and 0.05～the residue of 10%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, calendic acid is 0.3～0.9:1 with the mass ratio of fatty acid, and described residue is free fatty and glycerol.
The present invention solves the technical scheme that second technical problem used: the preparation method rich in the diglyceride fluid composition of calendic acid in such scheme comprises the following steps:
The first step, the extraction of calendic acid:
(1) pretreatment: Flos Inulae seed is cleaned, drained, is dried at 40～60 DEG C；
(2) calendic acid triglyceride extracts: dried Flos Inulae seed obtains dry powder after pulverizing, dry powder is through solvent extraction supercritical extraction or directly colds pressing and squeezes to obtain calendic acid triglyceride crude extract, and the refine after degumming, deacidification, decolouring, deodorize, dewaxing of calendic acid triglyceride crude extract prepares calendic acid triglyceride；
(3) preparation of calendic acid: the calendic acid triglyceride prepared in described step (2) is obtained calendic acid after saponification, acidifying；
(4) purification: calendic acid step (3) obtained and calendic acid ester dissolve in organic solvent, two step freeze crystallization isolated purity be respectively the calendic acid of 96～98%；
Second step, the calendic acid of said extracted and glycerol are mixed to form mixture with the ratio of 3～9:1, add lipozyme RMIM in the mixture and carry out the prepared diglyceride fluid composition crude product rich in calendic acid of enzymic catalytic reaction under vacuo, reaction temperature is 30～60 DEG C, response time 6-12h, described mixture is 300～500:1 with the mass ratio of lipozyme RMIM.
3rd step, to the above-mentioned prepared diglyceride fluid composition crude product rich in calendic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, uses the method for decolouring, deodorize and filtration to refine the diglyceride fluid composition rich in calendic acid needed for acquisition the most again.
As preferably, the extractant in described step (2) is one or more mixture in normal hexane, petroleum ether, ether, ethanol, methanol, chloroform, n-butyl alcohol, acetone, hexamethylene.
As preferably, described two-step crystallization method includes that first step crystallization and second step crystallize, and the crystallization temperature of this first step crystallization is 4 DEG C, and crystallization time is 8-16h, and crystallization pressure is normal pressure；The crystallization temperature of second step crystallization is-20 DEG C～-70 DEG C, and crystallisation times is 3-5 time, and each crystallization time is 8-16h, and crystallization pressure is normal pressure.
The present invention solves the 3rd technical scheme that technical problem is used: should be rich in the application in functional food and medicine of the diglyceride fluid composition of calendic acid, and this functional food and medicine are at least applied to the wherein one side controlling in body weight, enhancing immunity, treatment and prevention inflammation.
Compared with prior art, it is an advantage of the current invention that: the diglyceride fluid composition rich in calendic acid in the present invention combines with calendic acid with triglyceride form, compared with conventional diglyceride product, the preventive effect to fat generation can be strengthened, thus reach to control the purpose of body weight, and said composition also has various nutritional labelings and the physiological advantages of calendic acid in addition to having the structural stability of oil, hence in so that the product prepared with said composition for active component more superiority compared with conventional products, the most both there is the effect of weight reducing of diglyceride, also there is the antiinflammatory of calendic acid simultaneously, the effects such as fat-reducing, so that said composition can be widely used in control body weight, improve in blood fat and the functional food of raising immunity and medicine.Meanwhile, in the preparation process of said composition, prepare calendic acid, gold small cup seed abundance with gold small cup seed for raw material, edible safety is high, and the calendic acid high purity 96～98% prepared, in a word, the preparation technology of said composition is simple, and low cost has broad application prospects.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1:
Collecting Flos Inulae seed, pulverize to obtain dry powder 1000g after 40 DEG C of oven for drying, obtain the triglyceride crude extract of green with the petroleum ether of 5 times of volumes at less than 60 DEG C after reflux, extract, 6h, oil yield is 28.2%.Take triglyceride crude extract 50mL and add the potassium hydroxide-ethanol solution 200mL of 2M 90% saponification 2h at nitrogen protects lower 60 DEG C; add three extractings of 50mL petroleum ether after adding 50mL water and remove not saponification compound; add in 6M hydrochloric acid 100mL and go to upper strata to obtain petroleum ether solution with petroleum ether extracting after acidifying, then after rotary evaporation in vacuo, obtaining calendic acid crude extract.Calendic acid crude extract dissolves in ethanol, and the lower 4 DEG C of crystallization 8h of normal pressure remove satisfied fatty acid, and the ethanol solution obtained crystallizes 16h in subzero 20 DEG C the most at ambient pressure, is repeated 3 times the highly purified calendic acid of freezing and crystallizing isolated.The calendic acid using above-mentioned technique to prepare in the present embodiment reaches 97% through gas chromatographic analysis purity.
The calendic acid of said extracted and glycerol are mixed to form mixture with the ratio of 3:1, add lipozyme RMIM (Novozymes Company of Denmark) in the mixture and carry out the prepared diglyceride fluid composition crude product rich in calendic acid of enzymic catalytic reaction under vacuo, reaction temperature is 30 DEG C, response time 6h, said mixture is 300:1 with the mass ratio of lipozyme RMIM.To the above-mentioned prepared diglyceride fluid composition crude product rich in calendic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, the method for decolouring, deodorize and filtration is used to refine the diglyceride fluid composition rich in calendic acid needed for acquisition the most again.
After testing, diglyceride fluid composition rich in calendic acid prepared by the present embodiment is made up of following components in parts by weight: the diglyceride of 50%, the triglyceride of 30%, the monoglyceride of 10% and the residue of 10%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, calendic acid is 0.3:1 with the mass ratio of fatty acid, and above-mentioned residue is free fatty and glycerol.
Embodiment 2:
Collect Flos Inulae seed, the dry powder 1000g of particle diameter 0.4～0.5mm is pulverized to obtain after natural air drying under sunlight, at 30MPa, use SCF-CO 2 (the HA221-50-06 type supercritical extraction unit that Nantong city Huaan supercritical extraction unit produces) 2h under the conditions of 40 DEG C, obtaining the triglyceride crude extract (crude oil) of green at separating pressure 15MPa, separation temperature 50 DEG C, oil yield is 30.2%；Crude oil refine after degumming, deacidification, decolouring, deodorize, dewaxing prepares triglyceride.Take triglyceride crude extract 50mL and add the potassium hydroxide-ethanol solution 200mL of 2M 90% saponification 2h at nitrogen protects lower 60 DEG C; add three extractings of 50mL petroleum ether after adding 50mL water and remove not saponification compound; add in 6M hydrochloric acid 100mL and go to upper strata to obtain petroleum ether solution with petroleum ether extracting after acidifying, then after rotary evaporation in vacuo, obtaining calendic acid crude extract.Calendic acid crude extract dissolves in acetone, and the lower 4 DEG C of crystallization 8h of normal pressure remove satisfied fatty acid, then crystallize 8h in subzero 45 DEG C at ambient pressure, repeat more than 5 the highly purified calendic acid of freezing and crystallizing isolated.The calendic acid using above-mentioned technique to prepare in the present embodiment reaches 96% through gas chromatographic analysis purity.
The calendic acid of said extracted and glycerol are mixed to form mixture with the ratio of 9:1, add lipozyme RMIM (Novozymes Company of Denmark) in the mixture and carry out the prepared diglyceride fluid composition crude product rich in calendic acid of enzymic catalytic reaction under vacuo, reaction temperature is 60 DEG C, response time 10h, said mixture is 500:1 with the mass ratio of lipozyme RMIM.To the above-mentioned prepared diglyceride fluid composition crude product rich in calendic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, the method for decolouring, deodorize and filtration is used to refine the diglyceride fluid composition rich in calendic acid needed for acquisition the most again.
After testing, diglyceride fluid composition rich in calendic acid prepared by the present embodiment is made up of following components in parts by weight: the diglyceride of 70%, the triglyceride of 19%, the monoglyceride of 5% and the residue of 6%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, calendic acid is 0.9:1 with the mass ratio of fatty acid, and above-mentioned residue is free fatty and glycerol.
Embodiment 3:
Collect Flos Inulae seed, dry powder 1000g is pulverized to obtain after 40 DEG C of oven for drying, obtaining the calendic acid triglyceride crude extract of green after at room temperature extracting 24h with the chloroform of 5 times of volumes and methanol mixed solution (volume ratio is as 1:1), oil yield is 29.7%.Take triglyceride crude extract 100mL and add the sodium hydroxide ethanol solution 400mL of 2M 90% saponification 2h at nitrogen protects lower 60 DEG C; add three extractings of 100mL petroleum ether after adding 1000mL water and remove not saponification compound; add in 6M hydrochloric acid 200mL and go to upper strata to obtain petroleum ether solution with petroleum ether extracting after acidifying; calendic acid crude extract 4 DEG C of crystallization 10h at ambient pressure remove satisfied fatty acid; crystallize 12h in subzero 40 DEG C the most at ambient pressure, be repeated 4 times the highly purified calendic acid of freezing and crystallizing isolated.The calendic acid using above-mentioned technique to prepare in the present embodiment reaches 97% through gas chromatographic analysis purity.
The calendic acid of said extracted and glycerol are mixed to form mixture with the ratio of 6:1, add lipozyme RMIM (Novozymes Company of Denmark) in the mixture and carry out the prepared diglyceride fluid composition crude product rich in calendic acid of enzymic catalytic reaction under vacuo, reaction temperature is 45 DEG C, response time 8h, said mixture is 300:1 with the mass ratio of lipozyme RMIM.To the above-mentioned prepared diglyceride fluid composition crude product rich in calendic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, the method for decolouring, deodorize and filtration is used to refine the diglyceride fluid composition rich in calendic acid needed for acquisition the most again.
After testing, diglyceride fluid composition rich in calendic acid prepared by the present embodiment is made up of following components in parts by weight: the diglyceride of 85%, the triglyceride of 8%, the monoglyceride of 3% and the residue of 4%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, calendic acid is 0.5:1 with the mass ratio of fatty acid, and above-mentioned residue is free fatty and glycerol.
Embodiment 4:
Collecting gold small cup seed, pulverize to obtain the dry powder 1000g of particle diameter 0.4～0.5mm, obtain calendic acid triglyceride crude extract with the petroleum ether of 5 times of volumes at less than 80 DEG C after reflux, extract, 6h under sunlight after natural air drying, oil yield is 28.8%.The refine after degumming, deacidification, decolouring, deodorize, dewaxing of calendic acid triglyceride crude extract prepares triglyceride.Take triglyceride crude extract 50mL and add the potassium hydroxide-ethanol solution 200mL of 2M 90% saponification 2h at nitrogen protects lower 60 DEG C; add three extractings of 50mL petroleum ether after adding 50mL water and remove not saponification compound; add in 6M hydrochloric acid 100mL and go to upper strata to obtain petroleum ether solution with petroleum ether extracting after acidifying, then after rotary evaporation in vacuo, obtaining calendic acid crude extract.Calendic acid crude extract dissolves in acetone, and the lower 4 DEG C of crystallization 8h of normal pressure remove satisfied fatty acid, then crystallize 8h in subzero 45 DEG C at ambient pressure, repeat more than 5 the highly purified calendic acid of freezing and crystallizing isolated.The calendic acid using above-mentioned technique to prepare in the present embodiment reaches 98% through gas chromatographic analysis purity.
The calendic acid of said extracted and glycerol are mixed to form mixture with the ratio of 4:1, add lipozyme RMIM (Novozymes Company of Denmark) in the mixture and carry out the prepared diglyceride fluid composition crude product rich in calendic acid of enzymic catalytic reaction under vacuo, reaction temperature is 40 DEG C, response time 12h, said mixture is 400:1 with the mass ratio of lipozyme RMIM.To the above-mentioned prepared diglyceride fluid composition crude product rich in calendic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, the method for decolouring, deodorize and filtration is used to refine the diglyceride fluid composition rich in calendic acid needed for acquisition the most again.
After testing, diglyceride fluid composition rich in calendic acid prepared by the present embodiment is made up of following components in parts by weight: the diglyceride of 64.65%, the triglyceride of 35%, the monoglyceride of 0.3% and the residue of 0.05%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, calendic acid is 0.4:1 with the mass ratio of fatty acid, and above-mentioned residue is free fatty and glycerol.
Embodiment 5:
5.1, rich in control action to body weight of the diglyceride fluid composition of calendic acid
Appointing to take and carried out zoopery by the diglyceride fluid composition rich in calendic acid prepared in above-described embodiment 1～3, research said composition is the most inhibited to the increase of body weight and body fat.
The male ICR mouse of 6 week old is provided by Zhejiang Province's Experimental Animal Center, and ICR mice is randomly divided into 2 groups after adapting to 7 days, often group 10.Following 6 week, 2 groups of mices are in addition to feeding feedstuff, respectively to give each mice rich in the diglyceride fluid composition of calendic acid and per os gavage of consumption of calendic acid triglyceride oil (calendic acid content is for 62%) 50mg/kg body weight every day, measuring the body weight of each mice every two weeks, the meansigma methods of surveyed body weight is as shown in table 1.As it can be seen from table 1 compared with calendic acid triglyceride line of oils, Mouse Weight can be significantly inhibited rich in the diglyceride fluid composition of calendic acid and gather way, control the growth of body weight.
Table 1 is rich in the impact on Mouse Weight of the diglyceride fluid composition of calendic acid
5.2, the impact on immunologic function
Appointing to take and carried out zoopery by the diglyceride fluid composition rich in calendic acid prepared in above-described embodiment 1～3, whether research said composition has improvement result to immunologic function.
The male ICR mouse of 6 week old is provided by Zhejiang Province's Experimental Animal Center, ICR mice is randomly divided into 2 groups after adapting to 7 days, often group 10, following 3 week, 2 groups of mices are respectively to give each mice rich in the diglyceride fluid composition of calendic acid and per os gavage of consumption of calendic acid triglyceride oil (calendic acid content is for 62%) 50mg/kg body weight every day, and experiment separates each group of Mouse spleen cells and measures immunoglobulin after terminating.From table 2 it can be seen that diglyceride fluid composition group mouse immuning ball protein IgG and IgM content rich in calendic acid are significantly higher than calendic acid triglyceride line of oils mice.
Table 2 is rich in the impact on mouse boosting cell immunoglobulin of the diglyceride fluid composition of calendic acid
Claims (5)
1. the diglyceride fluid composition rich in calendic acid, it is characterised in that this diglyceride fluid composition presses matter
Amount percent meter is made up of following components: 50～the glycerol of the triglyceride of the diglyceride of 85%, 8～35%, 0.3～10%
One ester and 0.05～the residue of 10%, the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride
Middle calendic acid is 0.3～0.9:1 with the mass ratio of fatty acid, and described residue is free fatty and glycerol.
2. a preparation method for the diglyceride fluid composition rich in calendic acid as claimed in claim 1, its feature
It is to comprise the following steps: the first step, the extraction of calendic acid:
(1) pretreatment: Flos Inulae seed is cleaned, drained, is dried at 40～60 DEG C；
(2) calendic acid triglyceride extract: dried Flos Inulae seed pulverize after dry powder, dry powder through solvent extraction,
Supercritical extraction or directly cold pressing and squeeze to obtain calendic acid triglyceride crude extract, calendic acid triglyceride crude extract through degumming,
After deacidification, decolouring, deodorize, dewaxing, refine prepares calendic acid triglyceride；
(3) preparation of calendic acid: the calendic acid triglyceride prepared in described step (2) is obtained after saponification, acidifying
To calendic acid；
(4) purification: calendic acid step (3) obtained and calendic acid ester dissolve in organic solvent, freezing by two steps
Crystallization process isolated purity is respectively the calendic acid of 96～98%；
Second step, is mixed to form mixture with the ratio of 3～9:1, at this mixture by the calendic acid of said extracted and glycerol
Middle addition lipozyme RMIM, carries out enzymic catalytic reaction under vacuo and prepares the diglyceride fluid composition rich in calendic acid
Crude product, reaction temperature is 30～60 DEG C, response time 6-12h, described mixture and the mass ratio of lipozyme RMIM
It is 300～500:1；
3rd step, to the above-mentioned prepared diglyceride fluid composition crude product rich in calendic acid by molecular distillation fractionation of fatty
Acid and monoglyceride, use the method for decolouring, deodorize and filtration to refine the glycerol rich in calendic acid needed for acquisition the most again
Diester oil compositions.
3. the preparation method of the diglyceride fluid composition rich in calendic acid as claimed in claim 2, it is characterised in that
Extractant in described step (2) be normal hexane, petroleum ether, ether, ethanol, methanol, chloroform, n-butyl alcohol,
One or more mixture in acetone, hexamethylene.
4. the preparation method of the diglyceride fluid composition rich in calendic acid as claimed in claim 2, it is characterised in that
Described two-step crystallization method includes that first step crystallization and second step crystallize, and the crystallization temperature of this first step crystallization is 4 DEG C, crystallization
Time is 8-16h, and crystallization pressure is normal pressure；The crystallization temperature of second step crystallization is-20 DEG C～-70 DEG C, and crystallisation times is 3-5
Secondary, each crystallization time is 8-16h, and crystallization pressure is normal pressure.
5. the diglyceride fluid composition rich in calendic acid as claimed in claim 1 is in functional food and medicine
Application, this functional food and medicine be at least applied to control in body weight, enhancing immunity, treatment and prevention inflammation its
Middle one side.
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