CN101033188A - Method of preparing punicic acid, its salt and ester - Google Patents
Method of preparing punicic acid, its salt and ester Download PDFInfo
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- CN101033188A CN101033188A CN 200710067769 CN200710067769A CN101033188A CN 101033188 A CN101033188 A CN 101033188A CN 200710067769 CN200710067769 CN 200710067769 CN 200710067769 A CN200710067769 A CN 200710067769A CN 101033188 A CN101033188 A CN 101033188A
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- punicic acid
- acid
- drying
- ester
- punicic
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- CUXYLFPMQMFGPL-BGDVVUGTSA-N (9Z,11E,13Z)-octadecatrienoic acid Chemical compound CCCC\C=C/C=C/C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-BGDVVUGTSA-N 0.000 title claims abstract description 102
- CUXYLFPMQMFGPL-UYWAGRGNSA-N trichosanic acid Natural products CCCCC=C/C=C/C=CCCCCCCCC(=O)O CUXYLFPMQMFGPL-UYWAGRGNSA-N 0.000 title claims abstract description 26
- 150000002148 esters Chemical class 0.000 title claims abstract description 24
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title abstract description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 235000014360 Punica granatum Nutrition 0.000 claims abstract description 17
- 241000219991 Lythraceae Species 0.000 claims abstract description 16
- 239000000287 crude extract Substances 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 10
- 239000010779 crude oil Substances 0.000 claims abstract description 8
- 238000007605 air drying Methods 0.000 claims abstract description 7
- -1 punicic acid triglycerides Chemical class 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 238000000194 supercritical-fluid extraction Methods 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 238000003825 pressing Methods 0.000 claims abstract description 3
- 238000001291 vacuum drying Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- 241000218989 Trichosanthes Species 0.000 claims abstract 2
- 238000009777 vacuum freeze-drying Methods 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 9
- 238000007670 refining Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000007127 saponification reaction Methods 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 3
- 238000004332 deodorization Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 238000000199 molecular distillation Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 238000004042 decolorization Methods 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 235000018927 edible plant Nutrition 0.000 abstract 1
- 150000005691 triesters Chemical class 0.000 abstract 1
- 235000008326 Trichosanthes anguina Nutrition 0.000 description 8
- 244000078912 Trichosanthes cucumerina Species 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 7
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 7
- 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 5
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 229960004488 linolenic acid Drugs 0.000 description 5
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000030538 Thecla Species 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 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 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229960004232 linoleic acid Drugs 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 239000000284 extract Substances 0.000 description 2
- 125000005313 fatty acid group Chemical group 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000294611 Punica granatum Species 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000006023 Trichosanthes kirilowii Species 0.000 description 1
- 235000009818 Trichosanthes kirilowii Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000007894 caplet Substances 0.000 description 1
- 239000002775 capsule Substances 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940108924 conjugated linoleic acid Drugs 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
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- WCYAALZQFZMMOM-UHFFFAOYSA-N methanol;sulfuric acid Chemical compound OC.OS(O)(=O)=O WCYAALZQFZMMOM-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 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
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000005672 tetraenes Chemical class 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
本发明公开了一种石榴酸及其盐和酯的制备方法。以石榴籽、栝楼籽为原料，清洗、沥干后，低于60摄氏度干燥，干燥方法包括自然风干，低温烘干，真空干燥和冷冻干燥；干燥后的籽粒经过粉碎后，使用有机溶剂萃取、超临界萃取或籽粒直接冷压压榨得到石榴酸甘油三酯粗提物毛油，毛油经脱胶、脱酸、脱色、脱臭、脱蜡后，精炼制得石榴酸甘油三酯；石榴酸甘油三酯经皂化后得到石榴酸盐，进一步酸化后得到石榴酸。石榴酸经酯化后得到石榴酸酯，也可由石榴酸甘油三酯直接酯化得到石榴酸酯。按本发明方法制备的石榴酸及其酯和盐所含石榴酸纯度高达30－80％，本发明以天然可食用植物为原料，所得产品安全性高，有较为广阔的应用前景。The invention discloses a preparation method of punicic acid and its salt and ester. Pomegranate seeds and Trichosanthes seeds are used as raw materials. After washing and draining, they are dried below 60 degrees Celsius. The drying methods include natural air drying, low temperature drying, vacuum drying and freeze drying; after the dried seeds are crushed, they are extracted with organic solvents , supercritical extraction or direct cold pressing of seeds to obtain crude oil of punicic acid triglycerides crude extract, crude oil is degummed, deacidified, decolorized, deodorized, dewaxed, and then refined to obtain punicic acid triglycerides; punicic acid glycerol The triester is saponified to give punicate, which is further acidified to give punicic acid. Punicic acid can be esterified to give punicate, and can also be directly esterified to punicic acid triglyceride to get punicate. The purity of punicic acid contained in the punicic acid and its esters and salts prepared by the method of the invention is as high as 30-80%. The invention uses natural edible plants as raw materials, and the obtained product has high safety and broad application prospects.
Description
Technical field
The invention belongs to the applied chemistry technical field, relate to the method for from plant seed, extracting Trichosanoic acid and series product thereof, be specially and from snakegourd (Trichosanthes kirilowii Maxim) and pomegranate (Punica granatum Linn) seed, extract the method for preparing Trichosanoic acid and ester and salt.
Background technology
Conjugated fatty acids is to the polyunsaturated fatty acid position with conjugated double bond system and the common name of steric isomer.If between two two keys a methyl is arranged, we can be referred to as two keys that methyl separates, if a plurality of methyl are arranged, we are referred to as two keys that many methyl separate, if two two key conjugated together, we are referred to as conjugated fatty acids.Conjugated fatty acids can be the form of diene, triolefin or tetraene, prevailing conjugated fatty acids is octadecadienoic acid and punicic acid, conjugated linolic acid (conjugated linoleic acid just, CLA) and conjugate linolenic acid (conjugated linolenic acid, CLNA).Conjugate linolenic acid has multiple isomer owing to position of double bond is different with configuration, Trichosanoic acid (punicic acid) has another name called trichosanic acid, because of it is found from Semen Granati and snakegourd seed respectively, but is accredited as afterwards with a kind of material, the now unified Trichosanoic acid that is called, Trichosanoic acid is 9,11,13 two key conjugation, the two keys of 9 and 13 are configured as cis, 11 two keys are configured as trans conjugate linolenic acid (9c, 11t, 13c CLNA).Trichosanoic acid and 9c, 11t CLA (9,11 two key conjugation, 9 two keys are configured as cis, it is trans that 11 two keys are configured as, the most important a kind of isomer of conjugated linolic acid) similarity be that their the 9th and the 11st of fatty acid chain all is undersaturated pair of key, and steric configuration is identical.Trichosanoic acid can be converted to 9c in animal and human's body, therefore 11t CLA can be used as 9c, the natural diet source (Tsuzuki etc., 2006) that 11t CLA is important.
Conjugated fatty acids has and the conventional different special physiological function of polyunsaturated fatty acid.It is reported that CLA has a lot of favourable physiological functions, as improves the humans and animals blood fat, atherosclerosis, anti-obesity, anticancer, antihypertensive effect (Rainer etc., 2004).CLA is in the whole world, and particularly American-European countries is used widely as functional food such as fat-reducing, reducing blood-fat and healthcare products.CLA mainly exists in milk lipid, cheese and the ruminant meat.Yet, CLA content in these foods 1% (Sehat etc., 1998) of only having an appointment, this makes it can not make to contain sanatory food or the medicine of CLA with the CLA that natural resources exists.The CLA of commercial is rich in oleic oily isomerization by handle and obtains, and this isomerization product comprises equimolar 9c usually, 11t-CLA and 10t, 12c-CLA (Pariza etc., 2001) and other isomer.There is the consideration of aspects such as safety in the human consumer to the CLA of preparation of industrialization, CLA suitability for 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 to the human body beneficial.
Trichosanoic acid and 9c, the important difference of 11t-CLA is the 3rd undersaturated pair of key of Trichosanoic acid, Trichosanoic acid is at the 13rd two keys that a cis is arranged of fatty acid chain.So Trichosanoic acid has the feature of " polyunsaturated fatty acid " again.Polyunsaturated fatty acid has important nutritive value, and triglyceride level and cholesterol in the humans and animals body are had useful effect, can reduce the danger of cardiovascular and cerebrovascular diseases, promotes g and D.At present, polyunsaturated fatty acid is widely used in to add to and promotes growing and the development of intelligence of baby in the infant food.
Summary of the invention
The objective of the invention is at the situation that lacks natural CLA product in the prior art, propose development and utilization Trichosanoic acid and salt thereof and ester and be applied to the mankind as a kind of novel polyunsaturated fatty acid, the method of extracting Trichosanoic acid a kind of snakegourd seed from abundant raw material, the Semen Granati is provided for this reason, and relates to the extracting method of its middle product or series product pomegranate acid esters and pomegranate hydrochlorate.
The present invention is to realize by such scheme for reaching above purpose:
1, the preparation of Trichosanoic acid triglyceride level: from pomegranate and snakegourd fruit, collect seed, through making after pre-treatment, refining, the refining classification;
2, the preparation of pomegranate acid esters: directly carry out esterification by the Trichosanoic acid triglyceride level, make after the refining classification;
3, the preparation of pomegranate hydrochlorate: directly carry out saponification by the Trichosanoic acid triglyceride level, make after the refining classification;
4, the preparation of Trichosanoic acid: the Trichosanoic acid triglyceride level by above-mentioned steps 1 gained makes after saponification, acidifying, refining classification; Also can obtain Trichosanoic acid after the further acidifying of pomegranate hydrochlorate with step 3 gained;
In like manner, the pomegranate acid esters of step 2 gained of the present invention can be by the finished product Trichosanoic acid of above-mentioned steps 4 gained through over-churning, produces after the refining classification to obtain.
Trichosanoic acid of the present invention and ester thereof and salt are through gas chromatographic analysis, and its Trichosanoic acid content reaches 30%-80%.
Below further narrate Trichosanoic acid of the present invention and ester thereof, the preparation method of salt by comparatively concrete processing step:
(1) pre-treatment: collect pomegranate, snakegourd seed, clean, drain, drying; Drying temperature is lower than 60 degrees centigrade; Drying means comprises natural air drying, oven drying at low temperature, vacuum-drying, lyophilize etc.
(2) extract: dried seed is pulverized after solvent extraction, supercritical extraction or seed directly cold pressing to squeeze and is obtained Trichosanoic acid triglyceride level crude extract (crude oil), solvent extraction can be adopted one of organic solvents such as normal hexane, sherwood oil, ether, ethanol, ethanol, methyl alcohol, chloroform, propyl carbinol, acetone, hexanaphthene, also can adopt wherein any two or multiple mixed solvent; Crude oil through come unstuck, depickling, decolouring, deodorization, take off cured after refining make the Trichosanoic acid triglyceride level;
(3) saponification, acidifying: the above-mentioned Trichosanoic acid triglyceride level that obtains obtains the pomegranate hydrochlorate after saponification; Further obtain Trichosanoic acid after the acidifying;
(4) esterification: the above-mentioned Trichosanoic acid that obtains can obtain the pomegranate acid esters through esterification, also can obtain the pomegranate acid esters by the Trichosanoic acid triglyceride level esterification that above-mentioned steps (2) obtain;
(5) Trichosanoic acid of the present invention and ester thereof, salt stage treatment respectively, the different various purity products of Trichosanoic acid content, stage treatment comprises: divide carry, methods such as urea bag, differing temps precipitation, rectifying, molecular distillation or vacuum distilling.
Trichosanoic acid of the present invention and ester thereof and salt series product, it can be the form of solid, semisolid and liquid, can oral administration, enteron aisle is outer or mode such as injection is used, technology is made various formulations routinely, comprise oral liquid, elixir, capsule, Caplet, microcapsule, tablet, granule, pulvis, electuary, syrup, suspensoid, dripping pill, micropill, beverage and injection type, various formulations can comprise one or more seasoningss or tinting material.
Trichosanoic acid of the present invention and ester thereof and salt can be used in combination separately or with other activeconstituentss, and other activeconstituentss comprise: various VITAMIN, mineral substance, amino acid, polypeptide, other polyunsaturated fatty acid, conjugated linolic acid, conjugate linolenic acid.
The present invention compared with prior art has the following advantages:
(1) raw material of present method---Semen Granati and snakegourd seed ABUNDANT NATUREAL RESOURSES; (2) Trichosanoic acid of the present invention's preparation and ester thereof and salt are the product with the natural matter preparation, the edible safety height; (3) the Trichosanoic acid purity height of the present invention's preparation reaches 30-80%; (4) preparation technology of Trichosanoic acid of the present invention and ester thereof and salt is simple, and less investment has comparatively wide application prospect.
Embodiment
The preparation of embodiment 1, Trichosanoic acid triglyceride level:
Collect the pomegranate seed, pulverize behind the natural air drying under the sunlight the dry powder 400g of particle diameter 0.4-0.5mm, under 30MPa, 40 ℃ of conditions, adopt supercritical CO
2Extraction (Nantong city Huaan supercritical extraction unit produce HA221-50-06 type supercritical extraction unit) 2h obtains faint yellow Trichosanoic acid triglyceride level crude extract (crude oil) under 50 ℃ of separating pressure 15MPa, separation temperature, oil yield is 16%; Crude oil through come unstuck, depickling, decolouring, deodorization, take off cured after refining make the Trichosanoic acid triglyceride level.
Adopt above-mentioned technology make the Trichosanoic acid triglyceride level wherein Trichosanoic acid content reach 80%.
The preparation of embodiment 2, Trichosanoic acid:
Collect the snakegourd seed, pulverize behind the natural air drying under the sunlight dry powder 500g, after being lower than 60 ℃ of following refluxing extraction 6h, obtain green Trichosanoic acid triglyceride level crude extract with the normal hexane of 5 times of volumes, oil yield is 30.1%.Get Trichosanoic acid triglyceride level crude extract 50mL and add the potassium hydroxide-ethanol solution 200mL of 2M 90% in the following 60 ℃ of following saponification 2h of nitrogen protection; add three extractings of 50mL sherwood oil again behind the adding 50mL water and remove not saponification compound; add again among the 6M hydrochloric acid 100mL He after the acidifying and go to the upper strata to obtain petroleum ether solution, obtain Trichosanoic acid through behind the rotary evaporation in vacuo again with the sherwood oil extracting.
The Trichosanoic acid content that adopts above-mentioned technology to make reaches 31.5%.
The preparation of embodiment 3, Trichosanoic acid methyl esters:
Collect the pomegranate seed, pulverize behind the natural air drying under the sunlight dry powder 400g, after being lower than 80 ℃ of following refluxing extraction 6h, obtain Trichosanoic acid triglyceride level crude extract with the sherwood oil of 5 times of volumes, oil yield is 15.5%.The Trichosanoic acid triglyceride level crude extract 50mL that obtains, the sulfuric acid methanol solution 500mL that adds 0.5M reacts 30min down in 50 ℃ of water bath heat preservations, adds the 300mL petroleum ether extraction then, the Trichosanoic acid methyl esters that obtains behind the anhydrous sodium sulfate drying.
Adopt above-mentioned technology to make Trichosanoic acid methyl esters content and reach 77%.
The preparation of embodiment 4, Trichosanoic acid sodium:
Collect the snakegourd seed, pulverize behind the natural air drying under the sunlight dry powder 1000g, at room temperature obtain green Trichosanoic acid triglyceride level crude extract behind the lixiviate 24h with the chloroform and the methanol mixed solution (volume ratio is 1: 1) of 5 times of volumes, oil yield is 32.1%.The potassium hydroxide-ethanol solution 500mL that gets Trichosanoic acid triglyceride level crude extract 100mL adding 2M 90% is in the following 60 ℃ of following saponification 2h of nitrogen protection, and washing is squeezed, and obtains Trichosanoic acid sodium after dry the separation.
The Trichosanoic acid sodium content that adopts above-mentioned technology to make reaches 30%.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100677695A CN100441559C (en) | 2007-03-26 | 2007-03-26 | Process for preparing punicic acid and its salts and esters |
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| Application Number | Priority Date | Filing Date | Title |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106138026A (en) * | 2015-03-31 | 2016-11-23 | 浙江海洋学院 | A kind of diglyceride fluid composition rich in punicic acid and its preparation method and application |
| CN106135904A (en) * | 2015-03-31 | 2016-11-23 | 浙江海洋学院 | A kind of diglyceride fluid composition rich in calendic acid and its preparation method and application |
| CN106135902A (en) * | 2015-03-31 | 2016-11-23 | 浙江海洋学院 | A kind of diglyceride fluid composition rich in catalpic acid and its preparation method and application |
| CN106137944A (en) * | 2015-03-31 | 2016-11-23 | 浙江海洋学院 | A kind of diglyceride fluid composition rich in Cymbidium ensifolium (L.) Sw. acid and its preparation method and application |
| CN106822081A (en) * | 2016-12-30 | 2017-06-13 | 浙江海洋大学 | A kind of phosphatide type punicic acid fat or oil composition and its preparation method and application |
| CN106983777A (en) * | 2017-04-21 | 2017-07-28 | 上海衡志贸易有限公司 | Brown alga pomegranate seed nutriment and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1785218A (en) * | 2005-11-22 | 2006-06-14 | 华中科技大学 | Extractive of pomegranate seeds, prepn. method and application in preparing medicine thereof |
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2007
- 2007-03-26 CN CNB2007100677695A patent/CN100441559C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106138026A (en) * | 2015-03-31 | 2016-11-23 | 浙江海洋学院 | A kind of diglyceride fluid composition rich in punicic acid and its preparation method and application |
| CN106135904A (en) * | 2015-03-31 | 2016-11-23 | 浙江海洋学院 | A kind of diglyceride fluid composition rich in calendic acid and its preparation method and application |
| CN106135902A (en) * | 2015-03-31 | 2016-11-23 | 浙江海洋学院 | A kind of diglyceride fluid composition rich in catalpic acid and its preparation method and application |
| CN106137944A (en) * | 2015-03-31 | 2016-11-23 | 浙江海洋学院 | A kind of diglyceride fluid composition rich in Cymbidium ensifolium (L.) Sw. acid and its preparation method and application |
| CN106822081A (en) * | 2016-12-30 | 2017-06-13 | 浙江海洋大学 | A kind of phosphatide type punicic acid fat or oil composition and its preparation method and application |
| CN106983777A (en) * | 2017-04-21 | 2017-07-28 | 上海衡志贸易有限公司 | Brown alga pomegranate seed nutriment and preparation method thereof |
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| CN100441559C (en) | 2008-12-10 |
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