PL111647B1 - Method of isolation of thebaine from papaver bracteatum - Google Patents

Method of isolation of thebaine from papaver bracteatum Download PDF

Info

Publication number: PL111647B1
Authority: PL; Poland
Prior art keywords: thebaine; extraction; parts; papaver; solution
Prior art date: 1977-03-03

Application number

PL1978205023A

Other languages

English (en)

Polish (pl)

Other versions

PL205023A1 (pl

Original Assignee

Du Pont

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.)

1977-03-03

Filing date

1978-03-02

Publication date

1980-09-30

1978-03-02 Application filed by Du Pont filed Critical Du Pont

1979-04-09 Publication of PL205023A1 publication Critical patent/PL205023A1/xx

1980-09-30 Publication of PL111647B1 publication Critical patent/PL111647B1/pl

Links

FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 title claims description 63
229930003945 thebaine Natural products 0.000 title claims description 63
FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 title claims description 63
238000000034 method Methods 0.000 title claims description 32
241001596485 Papaver bracteatum Species 0.000 title claims description 15
235000018159 Papaver bracteatum Nutrition 0.000 title claims description 13
238000002955 isolation Methods 0.000 title 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
238000000605 extraction Methods 0.000 claims description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
241000196324 Embryophyta Species 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
239000000706 filtrate Substances 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 9
239000000463 material Substances 0.000 claims description 9
239000007788 liquid Substances 0.000 claims description 8
239000002245 particle Substances 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 7
239000002994 raw material Substances 0.000 claims description 7
241000218186 Papaver Species 0.000 claims description 6
235000011096 Papaver Nutrition 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
239000012535 impurity Substances 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
239000007791 liquid phase Substances 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 4
239000002910 solid waste Substances 0.000 claims description 4
239000002699 waste material Substances 0.000 claims description 4
241001302890 Parachondrostoma toxostoma Species 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
238000005352 clarification Methods 0.000 claims description 2
239000010808 liquid waste Substances 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims description 2
238000001556 precipitation Methods 0.000 claims description 2
239000010902 straw Substances 0.000 claims description 2
239000000243 solution Substances 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
235000008753 Papaver somniferum Nutrition 0.000 description 10
240000001090 Papaver somniferum Species 0.000 description 10
230000008569 process Effects 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
235000011114 ammonium hydroxide Nutrition 0.000 description 7
239000002585 base Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000010802 sludge Substances 0.000 description 6
235000012970 cakes Nutrition 0.000 description 5
239000000047 product Substances 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 4
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
239000000920 calcium hydroxide Substances 0.000 description 4
229910001861 calcium hydroxide Inorganic materials 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000010586 diagram Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000000227 grinding Methods 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000001376 precipitating effect Effects 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000036541 health Effects 0.000 description 2
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 description 1
241000218180 Papaveraceae Species 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229960004126 codeine Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
235000021463 dry cake Nutrition 0.000 description 1
238000009837 dry grinding Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000004880 explosion Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000003292 glue Substances 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 description 1
229960000240 hydrocodone Drugs 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002386 leaching Methods 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
229960002085 oxycodone Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000005549 size reduction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
YALHCTUQSQRCSX-UHFFFAOYSA-N sulfane sulfuric acid Chemical compound S.OS(O)(=O)=O YALHCTUQSQRCSX-UHFFFAOYSA-N 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
235000013522 vodka Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Extraction Or Liquid Replacement (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines Containing Plant Substances (AREA)
Processing Of Solid Wastes (AREA)

PL1978205023A 1977-03-03 1978-03-02 Method of isolation of thebaine from papaver bracteatum PL111647B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US77413777A	1977-03-03	1977-03-03
US84793377A	1977-11-02	1977-11-02

Publications (2)

Publication Number	Publication Date
PL205023A1 PL205023A1 (pl)	1979-04-09
PL111647B1 true PL111647B1 (en)	1980-09-30

Family

ID=27118846

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1978205023A PL111647B1 (en)	1977-03-03	1978-03-02	Method of isolation of thebaine from papaver bracteatum

Country Status (13)

Country	Link
JP (1)	JPS53130700A (fr)
AU (1)	AU3368178A (fr)
DE (1)	DE2808905A1 (fr)
DK (1)	DK57478A (fr)
FR (1)	FR2382454A1 (fr)
GB (1)	GB1586626A (fr)
IL (1)	IL54165A (fr)
IN (1)	IN148083B (fr)
IT (1)	IT1095452B (fr)
LU (1)	LU79165A1 (fr)
NL (1)	NL7802313A (fr)
NO (1)	NO780722L (fr)
PL (1)	PL111647B1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6067749A (en) *	1996-07-11	2000-05-30	Tasmanian Alkaloids Pty. Ltd.	Papaver somniferum strain with high concentration of thebaine and oripavine
US9131649B2 (en)	2008-03-07	2015-09-15	Tasmanian Alkaloids Pty. Ltd	Papaver somniferum strain with high concentration of thebaine
TR2021022235A2 (tr) *	2021-12-31	2022-02-21	Toprak Mahsulleri̇ Ofi̇si̇ Genel Müdürlüğü	Tebai̇nce zengi̇n haşhaş kapsülden alkol extraksi̇yonu i̇le tebai̇n eldesi̇

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD28733A (fr) *
DD112648A1 (fr) *	1972-10-13	1975-04-20

1978
- 1978-02-08 DK DK57478A patent/DK57478A/da not_active Application Discontinuation
- 1978-02-28 IT IT20727/78A patent/IT1095452B/it active
- 1978-02-28 AU AU33681/78A patent/AU3368178A/en active Pending
- 1978-03-01 IL IL54165A patent/IL54165A/xx unknown
- 1978-03-01 IN IN223/CAL/78A patent/IN148083B/en unknown
- 1978-03-02 GB GB8353/78A patent/GB1586626A/en not_active Expired
- 1978-03-02 NO NO780722A patent/NO780722L/no unknown
- 1978-03-02 FR FR7805985A patent/FR2382454A1/fr not_active Withdrawn
- 1978-03-02 PL PL1978205023A patent/PL111647B1/pl unknown
- 1978-03-02 NL NL7802313A patent/NL7802313A/xx not_active Application Discontinuation
- 1978-03-02 DE DE19782808905 patent/DE2808905A1/de not_active Withdrawn
- 1978-03-03 LU LU79165A patent/LU79165A1/fr unknown
- 1978-03-03 JP JP2437978A patent/JPS53130700A/ja active Pending

Also Published As

Publication number	Publication date
PL205023A1 (pl)	1979-04-09
IN148083B (fr)	1980-10-11
IT1095452B (it)	1985-08-10
IT7820727A0 (it)	1978-02-28
AU3368178A (en)	1979-09-06
LU79165A1 (fr)	1978-11-03
NL7802313A (nl)	1978-09-05
NO780722L (no)	1978-09-05
JPS53130700A (en)	1978-11-14
IL54165A0 (en)	1978-06-15
DK57478A (da)	1978-09-04
DE2808905A1 (de)	1978-09-07
IL54165A (en)	1981-12-31
GB1586626A (en)	1981-03-25
FR2382454A1 (fr)	1978-09-29

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