CN105566428A - Method for removing hyocholic acid from chenodeoxycholic acid - Google Patents

Method for removing hyocholic acid from chenodeoxycholic acid Download PDF

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CN105566428A
CN105566428A CN201610036122.5A CN201610036122A CN105566428A CN 105566428 A CN105566428 A CN 105566428A CN 201610036122 A CN201610036122 A CN 201610036122A CN 105566428 A CN105566428 A CN 105566428A
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acid
chenodiol
butylacetate
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crude product
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CN105566428B (en
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邓家国
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Changdeyungang Biotechnology Co ltd
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CHANGDE YUNGANG BIOTECHNOLOGY Co Ltd
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    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J9/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

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Abstract

The invention discloses a method for removing hyocholic acid from chenodeoxycholic acid. The method comprises the steps of dissolving, residue removing, complexing, crystallizing, centrifugal separating, emulsifying, acidifying, drying, mother liquor treating and the like; high-boiling-point butyl acetate is utilized as solvent, volatilization of the solvent is reduced, a good separation effect is achieved by utilizing the unique dissolution property of butyl acetate to impurities, and the solvent belongs to a three-level low-toxicity dangerous chemical; the selective complexing characteristic of sec-butylamine to bile acid is utilized, and the hyocholic acid and other impurities can be separated to a higher degree. According to the separation and purification method, impurity removing is qualified in one time, the loss rate of the chenodeoxycholic acid is 5% or below and is greatly lower than the effective ingredient loss of 30% in a conventional crystallization method, the solvent can be recycled, three wastes are not generated, and the method is an environment-friendly, low-cost and efficient separation method.

Description

A kind of method removing Iocholic acid from Chenodiol
Technical field
The present invention relates to Chenodiol extractive technique field, be specifically related to a kind of method removing Iocholic acid from Chenodiol.
Background technology
Chenodiol is the main raw material of ursodesoxycholic acid synthesis, and because the demand of ursodesoxycholic acid sharply increases, supply falls short of demand to cause Chenodiol.Fel Sus domestica is a kind of biology not renewable resource, and its TOTAL BILE ACID content is 10%, and the Chenodiol wherein contained accounts for 40% of TOTAL BILE ACID content, because of but a kind of very excellent Chenodiol raw materials for production.But due in Fel Sus domestica also containing the Iocholic acid accounting for TOTAL BILE ACID content 5%, and close with CDCA Acidity, in the process of Chenodiol processing extraction purification, easy crystallization, according to separation method---selective crystallization in mixed solvent conventional at present, its inferior separating effect, efficiency is low, and mother liquor needs fractional crystallization repeatedly, cause technical process long, solvent loss is large, also can take a large amount of Chenodiols out of, cause and waste and improve production cost in crystallisation process.
Summary of the invention
The present invention is directed to the problem that when above-mentioned Iocholic acid impurity is removed, difficulty is large, weak effect, efficiency are low, cost is high, provide a kind of simple efficient, low cost and the good method removing Iocholic acid from Chenodiol of elimination effect.
Technical scheme of the present invention: a kind of method removing Iocholic acid from Chenodiol, is characterized in that, comprise the steps:
(1) dissolve, remove slag: the chenodeoxycholic acid crude product extracted from Fel Sus domestica of getting rough segmentation de-oiling, add the butylacetate of 4-5 times of chenodeoxycholic acid crude product amount, backflow 1 hour after being heated to seethe with excitement, add gac, the deal of gac is the 8-10% of chenodeoxycholic acid crude product amount, stirring and refluxing 1 hour, is then filtered by the insulation of titanium rod filter bank, obtains Chenodiol butylacetate lysate;
(2) complexing, crystallization: Chenodiol butylacetate lysate is cooled to 40 DEG C, adds sec-butylamine, the deal of sec-butylamine is the 10-12% of chenodeoxycholic acid crude product amount, and insulated and stirred 1 hour, is cooled to normal temperature, and crystallization 4 hours, obtains mixing suspension liquid;
(3) centrifugation: will mix suspension liquid centrifugal, obtains CDCA acid ammonium salt and butylacetate mother liquor after solid-liquid separation, for subsequent use;
(4) emulsification, acidifying, drying: add water CDCA acid ammonium salt emulsification, the add-on of water is 4-4.5 times of chenodeoxycholic acid crude product amount, stirring is warming up to 35 DEG C, adds the hydrochloric acid that concentration is 10%, after adjust ph to 2-3, continue stirring 30 minutes, keep pH value 2-3 during stirring, then centrifugation, obtain Chenodiol finished product wet product, centrifugal sour water, wherein Chenodiol finished product wet product enters drying shed, dry Chenodiol finished product; The centrifugal sour water collected is used for lower batch of CDCA acid ammonium salt emulsified acid, recycle;
(5) mother liquid disposal: by butylacetate mother liquor vacuum concentration, vacuum tightness is 0.4 normal atmosphere, thickening temperature is 80 DEG C, obtain butylacetate, concentrated precipitate, wherein butylacetate is after acid treatment, recycle, and concentrated precipitate after drying, be used for foodstuff additive as mixing bile acide, take out.
Compared with prior art, advantage of the present invention: 1, utilize high boiling point butylacetate for solvent, decrease the volatilization of solvent, and utilize butylacetate to the stripping property of impurity uniqueness, reach good separating effect, this solvent is the dangerous categories of three class low toxicities.2, the characteristic of sec-butylamine selective complexation bile acide is utilized, can the separation Iocholic acid of higher degree and other impurity.3, the disposable removal of impurities of this separation purification method is qualified, and Chenodiol wastage rate are less than 5%, is significantly less than the effective constituent loss of conventional crystallization method 30%, and solvent all energy regenerations, producing without the three wastes, is a kind of environmental protection, low expense, efficiently separation method.
Embodiment
Now in conjunction with the embodiments, the invention will be further elaborated.
Embodiment one
Get chenodeoxycholic acid crude product (the HPLC content 61.3% extracted from Fel Sus domestica of 120 kg rough segmentation de-oiling, concrete Testing index sees attached list one), dropping into 1000L enamel extracts in still, add 600 kilograms of butylacetates, after being heated to seethe with excitement, backflow 1 hour, adds gac 12 kilograms, continues stirring and refluxing 1 hour, then filtered by the insulation of titanium rod filter bank, obtain Chenodiol butylacetate lysate.
By in Chenodiol butylacetate lysate suction 1000L enamel stillpot, be cooled to 40 DEG C, add sec-butylamine 12 kilograms, insulated and stirred 1 hour, be cooled to normal temperature 25 DEG C, crystallization 4 hours, obtains mixing suspension liquid.
Mixing suspension liquid is put into D800 clean closed type stainless steel whizzer centrifugal, after solid-liquid separation, obtain CDCA amine acid salt and butylacetate mother liquor, wherein CDCA acid ammonium salt net weight 95.1 kilograms.
95.1 kilograms of CDCA amine acid salts are dropped in 1000L enamel souring tank, add the emulsification of 500L pure water, stirring is warming up to 35 DEG C, slowly add the hydrochloric acid that concentration is 10%, after regulator solution pH value to 2-3, continue stirring 30 minutes, period keeps pH value 2-3, then be discharged in D800 type common stainless steel whizzer centrifugal, obtain Chenodiol finished product wet product, centrifugal sour water, wherein the pack of Chenodiol finished product wet product is sent in drying shed, use 4 × 0.25 air-flow boiling-bed dryings dry, obtain Chenodiol finished product 75.96 kilograms, after testing, its chromatographic content 92.1%, transformation efficiency (75.96 × 92.1%) ÷ (120 × 61.3) × 100/100=95.2%, Iocholic acid content 0.85%, concrete detected result sees attached list two, and the centrifugal sour water collected is temporary to glue tank, for lower batch of ammonium salt emulsification acidifying, recycle.
Butylacetate mother liquor suction 1000L vacuum concentration pot, vacuum 0.4 normal atmosphere, temperature 80 DEG C, concentrate to obtain butylacetate 558 kilograms, concentrated precipitate dry weight 33 kilograms, wherein butylacetate is after acid treatment, recycle; And concentrated precipitate is used for foodstuff additive as mixing bile acide after drying, take out.After testing, Iocholic acid content 21.09% in concentrated precipitate, CDCA acid content 6.5%, Hyodeoxycholic Acid, lithocholic acid and fat content amount to 11%, and concrete detection sees attached list three.
Embodiment two
Get chenodeoxycholic acid crude product (the HPLC content 59.7% extracted from Fel Sus domestica of 110 kilograms of rough segmentation de-oilings, concrete Testing index sees attached list one) drop in 1000L enamel extraction still, add 540 kilograms of butylacetates, backflow 1 hour after being heated to seethe with excitement, add gac 10 kilograms, continue stirring and refluxing 1 hour, then filtered by the insulation of titanium rod filter bank, obtain Chenodiol butylacetate lysate.
By in Chenodiol butylacetate lysate suction 1000L enamel stillpot, be cooled to 40 DEG C, add sec-butylamine 11 kilograms, insulated and stirred 1 hour, be cooled to normal temperature 25 DEG C, crystallization 4 hours, obtains mixing suspension liquid.
Mixing suspension liquid is put into D800 clean closed type stainless steel whizzer, carry out centrifugation, obtain CDCA amine acid salt and butylacetate mother liquor, wherein CDCA acid ammonium salt net weight 86.8 kilograms.
86.8 kilograms of CDCA amine acid salts are dropped in 1000L enamel souring tank, add the emulsification of 450L pure water, stirring is warming up to 35 DEG C, slowly add the hydrochloric acid that concentration is 10%, after adjust ph to 2-3, continue stirring 30 minutes, pH value 2-3 is kept during stirring, then centrifugation in D800 type common stainless steel whizzer is discharged to, obtain Chenodiol finished product wet product, centrifugal sour water, wherein drying shed is sent in the pack of Chenodiol finished product wet product, use 4 × 0.25 air-flow boiling-bed dryings dry, obtain Chenodiol finished product 67.38 kilograms, after testing, its chromatographic content 92.4%, transformation efficiency (67.38 × 92.4%) ÷ (110 × 59.7%) × 100/100=94.8%, Iocholic acid content is 0.89%, concrete detected result sees attached list two, and the centrifugal sour water collected is for lower batch of CDCA acid ammonium salt emulsified acid, recycle.
By butylacetate mother liquor suction 1000L vacuum concentration pot, vacuum 0.4 normal atmosphere, temperature 80 DEG C, concentrate to obtain butylacetate 501 kilograms, concentrated precipitate thing dry weight 30.1 kilograms, wherein butylacetate is after acid treatment, recycle, and concentrated precipitate is used for foodstuff additive as mixing bile acide after drying, takes out.After testing, Iocholic acid content 23.2% in concentrated precipitate, CDCA acid content 5.7%, Hyodeoxycholic Acid, lithocholic acid and fat content amount to 10.9%, and concrete detection sees attached list three.
Embodiment three
Get chenodeoxycholic acid crude product (the HPLC content 63.3% extracted from Fel Sus domestica of 125 kilograms of rough segmentation de-oilings, concrete Testing index sees attached list one) drop in 1000L enamel extraction still, add 625 kilograms of butylacetates, backflow 1 hour after being heated to seethe with excitement, add gac 12.5 kilograms, continue stirring and refluxing 1 hour, then filtered by the insulation of titanium rod filter bank, obtain Chenodiol butylacetate lysate.
By in Chenodiol butylacetate lysate suction 1000L enamel stillpot, be cooled to 40 DEG C, add sec-butylamine 12.5 kilograms, insulated and stirred 1 hour, be cooled to normal temperature 25 DEG C, crystallization 4 hours, obtains mixing suspension liquid.
Mixing suspension liquid is put into D800 clean closed type stainless steel whizzer, carry out centrifugation, obtain CDCA amine acid salt and butylacetate mother liquor, wherein CDCA acid ammonium salt net weight 100.6 kilograms.
100.6 kilograms of CDCA amine acid salts are dropped in 1000L enamel souring tank, add the emulsification of 500L pure water, stirring is warming up to 35 DEG C, slowly add the hydrochloric acid that concentration is 10%, after regulator solution pH value to 2-3, continue stirring 30 minutes, pH value 2-3 is kept during stirring, then centrifugation in D800 type common stainless steel whizzer is discharged to, obtain Chenodiol finished product wet product, centrifugal sour water, wherein drying shed is sent in the pack of Chenodiol finished product wet product, use 4 × 0.25 air-flow boiling-bed dryings dry, obtain Chenodiol finished product 80.73 kilograms, after testing, its chromatographic content 93.8%, transformation efficiency (80.7 × 93.8%) ÷ (125 × 63.3%) × 100/100=95.7%, Iocholic acid content is 0.66%, concrete detected result sees attached list two, and the centrifugal sour water collected is delivered in glue tank temporary, for lower batch of CDCA acid ammonium salt emulsified acid, recycle.
By butylacetate mother liquor suction 1000L vacuum concentration pot, vacuum 0.4 normal atmosphere, temperature 80 DEG C, concentrate to obtain butylacetate 558 kilograms, concentrated precipitate dry weight 35.7 kilograms, wherein butylacetate is after acid treatment, recycle, and concentrated precipitate is used for foodstuff additive as mixing bile acide after drying, takes out.After testing, Iocholic acid content 20.8% in concentrated precipitate, CDCA acid content 6.1%, Hyodeoxycholic Acid, lithocholic acid and fat content amount to 13.2%, and concrete detection sees attached list three.
Detect chenodeoxycholic acid crude product, finished product and tankage mixing bile acide thereof, its index parameter is as shown in subordinate list one, subordinate list two, subordinate list three.
Subordinate list one: chenodeoxycholic acid crude product assay (this content is HPLC marker method and detects, and lithocholic acid uses tlc)
Lot number Chenodiol Iocholic acid Hyodeoxycholic Acid Lithocholic acid Weight loss on drying
Example one (20150501) 61.3% 5.8% 0.37% ≤1.0% 2.5%
Example two (20150502) 59.7% 5.1% 0.47% ≤1.0% 2.8%
Example three (20150503) 63.3% 4.9% 0.35% ≤1.0% 2.1%
Subordinate list two: Chenodiol inspection after construction result (this content is HPLC marker method and detects, and lithocholic acid uses tlc)
Lot number Chenodiol Iocholic acid Hyodeoxycholic Acid Lithocholic acid Weight loss on drying 3-->
Example one (20150501) 92.1% 0.85% 0.34% ≤0.2% 1.3%
Example two (20150502) 92.4% 0.89% 0.41% ≤0.2% 0.9%
Example three (20150503) 93.8% 0.66% 0.27% ≤0.2% 0.77%
Subordinate list three: tankage assay (this content is HPLC external standard method and detects)
Lot number Chenodiol Iocholic acid Other TOTAL BILE ACID
Example one (20150501) 6.5% 21.09% 11%
Example two (20150502) 5.7% 23.2% 10.9%
Example three (20150503) 6.1% 20.8% 13.2%
Can illustrate according to above assay, by the Chenodiol after method purifying of the present invention, detect through high performance liquid chromatography, CDCA acid content at 92-94%, its major impurity: Hyodeoxycholic Acid is less than 0.5%, Iocholic acid is less than 1%, lithocholic acid is less than 0.2%, Iocholic acid list is assorted to be controlled within 1%, and other single mixing is less than 0.5% completely, has reached the quality standard of processing ursodesoxycholic acid EP7.0 and CP2010.

Claims (1)

1. from Chenodiol, remove a method for Iocholic acid, it is characterized in that, comprise the steps:
(1) dissolve, remove slag: the chenodeoxycholic acid crude product extracted from Fel Sus domestica of getting rough segmentation de-oiling, add the butylacetate of 4-5 times of chenodeoxycholic acid crude product amount, backflow 1 hour after being heated to seethe with excitement, add gac, the deal of gac is the 8-10% of chenodeoxycholic acid crude product amount, stirring and refluxing 1 hour, is then filtered by the insulation of titanium rod filter bank, obtains Chenodiol butylacetate lysate;
(2) complexing, crystallization: Chenodiol butylacetate lysate is cooled to 40 DEG C, adds sec-butylamine, the deal of sec-butylamine is the 10-12% of chenodeoxycholic acid crude product amount, and insulated and stirred 1 hour, is cooled to normal temperature, and crystallization 4 hours, obtains mixing suspension liquid;
(3) centrifugation: will mix suspension liquid centrifugal, obtains CDCA acid ammonium salt and butylacetate mother liquor after solid-liquid separation, for subsequent use;
(4) emulsification, acidifying, drying: add water CDCA acid ammonium salt emulsification, the add-on of water is 4-4.5 times of chenodeoxycholic acid crude product amount, stirring is warming up to 35 DEG C, adds the hydrochloric acid that concentration is 10%, after adjust ph to 2-3, continue stirring 30 minutes, keep pH value 2-3 during stirring, then centrifugation, obtain Chenodiol finished product wet product, centrifugal sour water, wherein Chenodiol finished product wet product enters drying shed, dry Chenodiol finished product; The centrifugal sour water collected is used for lower batch of CDCA acid ammonium salt emulsified acid, recycle;
(5) mother liquid disposal: by butylacetate mother liquor vacuum concentration, vacuum tightness is 0.4 normal atmosphere, thickening temperature is 80 DEG C, obtain butylacetate, concentrated precipitate, wherein butylacetate is after acid treatment, recycle, and concentrated precipitate after drying, be used for foodstuff additive as mixing bile acide, take out.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108299538A (en) * 2018-03-09 2018-07-20 常德云港生物科技有限公司 A method of removing different ursodesoxycholic acid in duck bile
CN109810159A (en) * 2019-01-22 2019-05-28 常德云港生物科技有限公司 A kind of method that allocholic acid yield can be improved from duck bile
CN110256517A (en) * 2019-07-19 2019-09-20 中山百灵生物技术有限公司 A method of producing high-purity chenodeoxy cholic acid from pig's bile or leftover bits and pieces
CN110790805A (en) * 2019-11-14 2020-02-14 湖南九典制药股份有限公司 Method for extracting chenodeoxycholic acid from pig bile paste
CN112062802A (en) * 2019-06-11 2020-12-11 四川澄华生物科技有限公司 Chenodeoxycholic acid butyl acetate extracting solution and preparation method thereof, and chenodeoxycholic acid ammonium salt and chenodeoxycholic acid preparation method

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CN1432579A (en) * 2002-12-27 2003-07-30 贵州省生物技术研究开发基地 Refining process of chenodeoxcholic acid
CN1869044A (en) * 2006-06-09 2006-11-29 沈阳化工学院 Separation purification preparation method of chenodeoxycholic acid in pig's bile
CN101948496A (en) * 2010-09-21 2011-01-19 湖南凯勒迪化学科技有限公司 Method for extracting chenodeoxycholic acid from bile of fowl
CN102766185A (en) * 2012-08-02 2012-11-07 苏州天绿生物制药有限公司 Method for respectively recovering ursodesoxycholic acid and chenodeoxycholic acid from ursodesoxycholic acid waste mother liquor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1432579A (en) * 2002-12-27 2003-07-30 贵州省生物技术研究开发基地 Refining process of chenodeoxcholic acid
CN1869044A (en) * 2006-06-09 2006-11-29 沈阳化工学院 Separation purification preparation method of chenodeoxycholic acid in pig's bile
CN101948496A (en) * 2010-09-21 2011-01-19 湖南凯勒迪化学科技有限公司 Method for extracting chenodeoxycholic acid from bile of fowl
CN102766185A (en) * 2012-08-02 2012-11-07 苏州天绿生物制药有限公司 Method for respectively recovering ursodesoxycholic acid and chenodeoxycholic acid from ursodesoxycholic acid waste mother liquor

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108299538A (en) * 2018-03-09 2018-07-20 常德云港生物科技有限公司 A method of removing different ursodesoxycholic acid in duck bile
CN109810159A (en) * 2019-01-22 2019-05-28 常德云港生物科技有限公司 A kind of method that allocholic acid yield can be improved from duck bile
CN112062802A (en) * 2019-06-11 2020-12-11 四川澄华生物科技有限公司 Chenodeoxycholic acid butyl acetate extracting solution and preparation method thereof, and chenodeoxycholic acid ammonium salt and chenodeoxycholic acid preparation method
CN110256517A (en) * 2019-07-19 2019-09-20 中山百灵生物技术有限公司 A method of producing high-purity chenodeoxy cholic acid from pig's bile or leftover bits and pieces
CN110256517B (en) * 2019-07-19 2021-03-09 中山百灵生物技术股份有限公司 Method for producing high-purity chenodeoxycholic acid from pig bile or leftovers
CN110790805A (en) * 2019-11-14 2020-02-14 湖南九典制药股份有限公司 Method for extracting chenodeoxycholic acid from pig bile paste
CN110790805B (en) * 2019-11-14 2022-08-30 湖南九典制药股份有限公司 Method for extracting chenodeoxycholic acid from pig bile paste

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