CA1293250C - Separation et purification de beta-cyclodextrines ramifiees - Google Patents

Separation et purification de beta-cyclodextrines ramifiees

Info

Publication number: CA1293250C
Authority: CA; Canada
Prior art keywords: beta; solution; cyclodextrin; precipitate; liquor
Prior art date: 1987-07-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA000570649A

Other languages

English (en)

Inventor

Robert N. Ammeraal

David J. Gottneid

Allan R. Hedges

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Cerestar USA Inc

Original Assignee

American Maize Products Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-07-08

Filing date

1988-06-28

Publication date

1991-12-17

1988-06-28 Application filed by American Maize Products Co filed Critical American Maize Products Co

1988-06-28 Priority to CA000570649A priority Critical patent/CA1293250C/fr

1991-12-17 Application granted granted Critical

1991-12-17 Publication of CA1293250C publication Critical patent/CA1293250C/fr

2008-12-17 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 132
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims abstract description 119
235000011175 beta-cyclodextrine Nutrition 0.000 title claims abstract description 117
238000000746 purification Methods 0.000 title abstract description 7
238000000926 separation method Methods 0.000 title abstract description 7
239000002244 precipitate Substances 0.000 claims abstract description 80
229960004853 betadex Drugs 0.000 claims abstract description 75
239000001116 FEMA 4028 Substances 0.000 claims abstract description 74
238000000034 method Methods 0.000 claims abstract description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 18
238000001914 filtration Methods 0.000 claims description 9
238000005406 washing Methods 0.000 claims description 9
238000002156 mixing Methods 0.000 claims description 7
238000011084 recovery Methods 0.000 claims description 7
238000001035 drying Methods 0.000 claims description 6
239000000047 product Substances 0.000 claims description 4
239000000243 solution Substances 0.000 abstract description 85
239000007864 aqueous solution Substances 0.000 abstract description 3
229920002472 Starch Polymers 0.000 description 19
235000019698 starch Nutrition 0.000 description 19
239000008107 starch Substances 0.000 description 19
239000007787 solid Substances 0.000 description 18
108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 description 14
239000000706 filtrate Substances 0.000 description 10
238000000605 extraction Methods 0.000 description 9
125000002015 acyclic group Chemical group 0.000 description 8
239000002002 slurry Substances 0.000 description 8
229920000945 Amylopectin Polymers 0.000 description 7
229920001353 Dextrin Polymers 0.000 description 7
239000004375 Dextrin Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
235000019425 dextrin Nutrition 0.000 description 7
229940088598 enzyme Drugs 0.000 description 6
TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
229920000856 Amylose Polymers 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 5
239000012065 filter cake Substances 0.000 description 5
235000014633 carbohydrates Nutrition 0.000 description 4
150000001720 carbohydrates Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
229940097362 cyclodextrins Drugs 0.000 description 4
239000002904 solvent Substances 0.000 description 4
241000196324 Embryophyta Species 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
241000193752 Bacillus circulans Species 0.000 description 1
241000194107 Bacillus megaterium Species 0.000 description 1
241000194110 Bacillus sp. (in: Bacteria) Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241000178960 Paenibacillus macerans Species 0.000 description 1
241001237728 Precis Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
102000004139 alpha-Amylases Human genes 0.000 description 1
108090000637 alpha-Amylases Proteins 0.000 description 1
229940024171 alpha-amylase Drugs 0.000 description 1
229940043377 alpha-cyclodextrin Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
229940080345 gamma-cyclodextrin Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
-1 seven Chemical compound 0.000 description 1
239000000126 substance Substances 0.000 description 1

Landscapes

Polysaccharides And Polysaccharide Derivatives (AREA)

CA000570649A 1987-07-08 1988-06-28 Separation et purification de beta-cyclodextrines ramifiees Expired - Lifetime CA1293250C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000570649A CA1293250C (fr)	1987-07-08	1988-06-28	Separation et purification de beta-cyclodextrines ramifiees

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US071,097		1987-07-08
CA000570649A CA1293250C (fr)	1987-07-08	1988-06-28	Separation et purification de beta-cyclodextrines ramifiees

Publications (1)

Publication Number	Publication Date
CA1293250C true CA1293250C (fr)	1991-12-17

Family

ID=4138287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000570649A Expired - Lifetime CA1293250C (fr)	1987-07-08	1988-06-28	Separation et purification de beta-cyclodextrines ramifiees

Country Status (1)

Country	Link
CA (1)	CA1293250C (fr)

1988
- 1988-06-28 CA CA000570649A patent/CA1293250C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1996-06-17	MKLA	Lapsed

Publication	Publication Date	Title
US4840679A (en)	1989-06-20	Purification and separation of branched beta-cyclodextrins
JP3751033B2 (ja)	2006-03-01	長鎖イヌリンの製造方法
US5376641A (en)	1994-12-27	Method for making a steroid water soluble
US4920214A (en)	1990-04-24	Process for producing modified cyclodextrins
US4738923A (en)	1988-04-19	Process for producing and separating cyclodextrins
EP0389586B1 (fr)	1995-02-08	Procede de fabrication de cyclodextrines ramifiees et produit ainsi produit
CN111394406B (zh)	2022-05-31	一种γ-环糊精的制备方法
US4960697A (en)	1990-10-02	Recovery of polysaccharides by employing a divalent cation with a water miscible organic solvent
CA1293250C (fr)	1991-12-17	Separation et purification de beta-cyclodextrines ramifiees
US4167622A (en)	1979-09-11	Process for preparing hydroxyethyl starch suitable as a plasma expander
US5658390A (en)	1997-08-19	Purification of beta cyclodextrin
EP0381747A4 (en)	1991-09-11	Water soluble branched beta cyclodextrin steroid complex
CN111394407B (zh)	2022-06-14	一种γ-环糊精的制备方法
US5032182A (en)	1991-07-16	Branched cyclodextrins
CN117756963A (zh)	2024-03-26	一种羟丙基-γ-环糊精的制法
KR100486042B1 (ko)	2005-04-29	효소 처리에 의한 키틴 저분자당 및 올리고당의 제조방법
KR100252704B1 (ko)	2000-04-15	고순도 결정성 nocc의 제조방법 및 효소를 이용한 수용성키토산의 분자량 조절방법
Kardošová et al.	1983	Glucan isolated from leaves of Althaea officinalis L.
KR0136363B1 (ko)	1998-04-25	사이클로덱스트린의 제조방법
DE19712931B4 (de)	2004-08-05	Verfahren zur Gewinnung von Hyaluronsäure
KR100192061B1 (ko)	1999-06-15	고순도 사이클로덱스트린의 제조방법
JPS61280291A (ja)	1986-12-10	フラクト−スポリマ−の製造方法
HUT71705A (en)	1996-01-29	Purification of beta cyclodextrin
MACIEJEWSKI	1980	Dehydrochlorinated Adduct of/3-Cyclodextrin and Poly (vinylidene Chloride)
JPH0574351B2 (fr)	1993-10-18