DD267664A5 - Verfahren zur herstellung von kamillenoelen mit hohem gehalt an natuerlichen cis- und trans-spiroethern - Google Patents

Verfahren zur herstellung von kamillenoelen mit hohem gehalt an natuerlichen cis- und trans-spiroethern Download PDF

Info

Publication number: DD267664A5
Authority: DD; German Democratic Republic
Prior art keywords: chamomile; distillation; spiroethers; trans; oil
Prior art date: 1987-02-13

Application number

DD88312883A

Other languages

German (de)

English (en)

Inventor

Reinhold Carle

Otto Isaac

Original Assignee

��@��@��k��

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.)

1987-02-13

Filing date

1988-02-12

Publication date

1989-05-10

1988-02-12 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1989-05-10 Publication of DD267664A5 publication Critical patent/DD267664A5/de

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 12
239000003921 oil Substances 0.000 title description 18
235000007232 Matricaria chamomilla Nutrition 0.000 claims abstract description 39
235000007866 Chamaemelum nobile Nutrition 0.000 claims abstract description 36
238000000605 extraction Methods 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 16
235000020221 chamomile extract Nutrition 0.000 claims abstract description 15
235000019480 chamomile oil Nutrition 0.000 claims abstract description 14
239000010628 chamomile oil Substances 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 13
229940119217 chamomile extract Drugs 0.000 claims abstract description 7
238000001256 steam distillation Methods 0.000 claims abstract description 6
240000003538 Chamaemelum nobile Species 0.000 claims abstract 5
238000004821 distillation Methods 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 3
239000002689 soil Substances 0.000 abstract 1
244000042664 Matricaria chamomilla Species 0.000 description 35
235000019198 oils Nutrition 0.000 description 17
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 description 13
229940079593 drug Drugs 0.000 description 11
239000003814 drug Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
239000000341 volatile oil Substances 0.000 description 10
229930195733 hydrocarbon Natural products 0.000 description 9
150000002430 hydrocarbons Chemical class 0.000 description 9
239000004215 Carbon black (E152) Substances 0.000 description 8
229940070641 chamomile flowers Drugs 0.000 description 8
239000012071 phase Substances 0.000 description 7
RKBAYVATPNYHLW-NFAWXSAZSA-N Bisabolol oxide B Natural products OC(C)(C)[C@@H]1O[C@](C)([C@@H]2CC=C(C)CC2)CC1 RKBAYVATPNYHLW-NFAWXSAZSA-N 0.000 description 6
RKBAYVATPNYHLW-UHFFFAOYSA-N Bisabolol oxide B Chemical compound C1CC(C)=CCC1C1(C)OC(C(C)(C)O)CC1 RKBAYVATPNYHLW-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000001500 (2R)-6-methyl-2-[(1R)-4-methyl-1-cyclohex-3-enyl]hept-5-en-2-ol Substances 0.000 description 5
NJLYCNZOTQCQMC-UHFFFAOYSA-N 2-hexa-2,4-diynyl-1,6-dioxaspiro[4.4]non-3-ene Chemical compound C1=CC(CC#CC#CC)OC11OCCC1 NJLYCNZOTQCQMC-UHFFFAOYSA-N 0.000 description 5
WJHRAVIQWFQMKF-UHFFFAOYSA-N Bisabolol oxide A Natural products C1CC(C)=CCC1C1(C)OC(C)(C)C(O)CC1 WJHRAVIQWFQMKF-UHFFFAOYSA-N 0.000 description 5
WJHRAVIQWFQMKF-IPYPFGDCSA-N Bisabolol oxide A Chemical compound C1CC(C)=CC[C@H]1[C@@]1(C)OC(C)(C)[C@@H](O)CC1 WJHRAVIQWFQMKF-IPYPFGDCSA-N 0.000 description 5
GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical compound CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 5
239000013543 active substance Substances 0.000 description 5
229940036350 bisabolol Drugs 0.000 description 5
239000000654 additive Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
208000035199 Tetraploidy Diseases 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
PMRJYBALQVLLSJ-UHFFFAOYSA-N chamazulene Natural products CCC1=CC2=C(C)CCC2=CC=C1 PMRJYBALQVLLSJ-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical class OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
DBZHHRPNWDNKNX-UHFFFAOYSA-N Chamazulen Natural products CC1=CC=C2C=C(C=CC(=C12)C(C)C)C DBZHHRPNWDNKNX-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
239000012675 alcoholic extract Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000001303 quality assessment method Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000005185 salting out Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 2
AILDTIZEPVHXBF-UHFFFAOYSA-N Argentine Natural products C1C(C2)C3=CC=CC(=O)N3CC1CN2C(=O)N1CC(C=2N(C(=O)C=CC=2)C2)CC2C1 AILDTIZEPVHXBF-UHFFFAOYSA-N 0.000 description 1
240000006497 Dianthus caryophyllus Species 0.000 description 1
235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
235000004429 Matricaria chamomilla var recutita Nutrition 0.000 description 1
244000308495 Potentilla anserina Species 0.000 description 1
235000016594 Potentilla anserina Nutrition 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
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
-1 aliphatic alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Chemical class 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
150000001545 azulenes Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
229930003944 flavone Natural products 0.000 description 1
150000002213 flavones Chemical class 0.000 description 1
235000011949 flavones Nutrition 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
230000005484 gravity Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052500 inorganic mineral Chemical class 0.000 description 1
239000011707 mineral Chemical class 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011555 saturated liquid Substances 0.000 description 1
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
235000010378 sodium ascorbate Nutrition 0.000 description 1
229960005055 sodium ascorbate Drugs 0.000 description 1
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical class [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Natural Medicines & Medicinal Plants (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Botany (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pain & Pain Management (AREA)
Mycology (AREA)
Microbiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medical Informatics (AREA)
Alternative & Traditional Medicine (AREA)
Biotechnology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Plant Substances (AREA)
Fats And Perfumes (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Compounds Of Unknown Constitution (AREA)
Jigs For Machine Tools (AREA)
Valve-Gear Or Valve Arrangements (AREA)
Tires In General (AREA)
Gears, Cams (AREA)

DD88312883A 1987-02-13 1988-02-12 Verfahren zur herstellung von kamillenoelen mit hohem gehalt an natuerlichen cis- und trans-spiroethern DD267664A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3704519		1987-02-13

Publications (1)

Publication Number	Publication Date
DD267664A5 true DD267664A5 (de)	1989-05-10

Family

ID=6320906

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88312883A DD267664A5 (de)	1987-02-13	1988-02-12	Verfahren zur herstellung von kamillenoelen mit hohem gehalt an natuerlichen cis- und trans-spiroethern

Country Status (18)

Country	Link
US (1)	US5902587A (da)
EP (1)	EP0285752B1 (da)
AR (1)	AR240401A1 (da)
AT (1)	ATE96328T1 (da)
BR (1)	BR8800572A (da)
CA (1)	CA1327205C (da)
DD (1)	DD267664A5 (da)
DE (1)	DE3885137D1 (da)
DK (1)	DK175030B1 (da)
ES (1)	ES2044980T3 (da)
FI (1)	FI93306C (da)
HU (1)	HU201877B (da)
IE (1)	IE61572B1 (da)
MX (1)	MX10394A (da)
NO (1)	NO174033C (da)
PL (1)	PL159197B1 (da)
SK (1)	SK281631B6 (da)
YU (1)	YU47189B (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6300370B1 (en) *	1987-02-13	2001-10-09	Asta Medica Aktiengesellschaft	Camomile oils having a high content of natural poly-ynes and process for their preparation
GB2377218A (en) *	2001-05-04	2003-01-08	Gw Pharmaceuticals Ltd	Process and apparatus for extraction of active substances and enriched extracts from natural products
GB0819635D0 (en) *	2008-10-27	2008-12-03	Auron Invest Ltd	A composition for the treatment of hypertension
BR112014002607A2 (pt) *	2011-08-01	2017-02-21	Rhodia Operations	uso de solventes em favor do meio ambiente para substituir solventes á base de glicol
CN109152726B (zh) *	2016-02-25	2022-05-13	Isp投资有限公司	用获得自活植物的成分减轻阳光的不利影响

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2402802C3 (de) *	1974-01-22	1979-06-13	Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt	Gewinnung einer Kamillendroge mit hohem Chamazulen- und Bisabololgehalt
DE2709033C2 (de) *	1977-03-02	1984-07-26	Degussa Ag, 6000 Frankfurt	Kamillenextrakte und ihre Herstellung
GB2167955B (en) *	1983-06-29	1988-12-07	Degussa	Preparation of camomile extracts and ethereal oils
IN163594B (da) *	1984-03-16	1988-10-15	Degussa
MX161477A (es) *	1984-09-19	1990-09-28	Degussa	Procedimiento para extraer los constituyentes de la manzanilla
DE3542756C3 (de) *	1984-12-19	1997-09-04	Asta Medica Ag	Verfahren zur Herstellung einer neuen tetraploiden und bisabololreichen Kamille mit verbesserten Eigenschaften

1988
- 1988-01-23 ES ES88101008T patent/ES2044980T3/es not_active Expired - Lifetime
- 1988-01-23 DE DE88101008T patent/DE3885137D1/de not_active Expired - Lifetime
- 1988-01-23 EP EP88101008A patent/EP0285752B1/de not_active Expired - Lifetime
- 1988-01-23 AT AT88101008T patent/ATE96328T1/de not_active IP Right Cessation
- 1988-02-01 AR AR309989A patent/AR240401A1/es active
- 1988-02-11 BR BR8800572A patent/BR8800572A/pt not_active IP Right Cessation
- 1988-02-11 YU YU26388A patent/YU47189B/sh unknown
- 1988-02-11 SK SK867-88A patent/SK281631B6/sk unknown
- 1988-02-11 PL PL1988270590A patent/PL159197B1/pl unknown
- 1988-02-12 DD DD88312883A patent/DD267664A5/de not_active IP Right Cessation
- 1988-02-12 CA CA000558851A patent/CA1327205C/en not_active Expired - Lifetime
- 1988-02-12 DK DK198800734A patent/DK175030B1/da not_active IP Right Cessation
- 1988-02-12 HU HU88682A patent/HU201877B/hu unknown
- 1988-02-12 IE IE38988A patent/IE61572B1/en not_active IP Right Cessation
- 1988-02-12 MX MX1039488A patent/MX10394A/es unknown
- 1988-02-12 FI FI880659A patent/FI93306C/fi active IP Right Grant
- 1988-02-12 NO NO880629A patent/NO174033C/no not_active IP Right Cessation
1992
- 1992-07-01 US US07/908,856 patent/US5902587A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO880629D0 (no)	1988-02-12
EP0285752A2 (de)	1988-10-12
ES2044980T3 (es)	1994-01-16
FI93306B (fi)	1994-12-15
YU47189B (sh)	1995-01-31
NO174033C (no)	1994-03-09
CA1327205C (en)	1994-02-22
EP0285752B1 (de)	1993-10-27
DK73488D0 (da)	1988-02-12
DE3885137D1 (de)	1993-12-02
PL270590A1 (en)	1989-09-18
FI93306C (fi)	1995-03-27
IE880389L (en)	1989-08-12
HUT46218A (en)	1988-10-28
PL159197B1 (pl)	1992-11-30
NO880629L (no)	1988-08-15
BR8800572A (pt)	1988-09-27
DK175030B1 (da)	2004-05-03
MX10394A (es)	1993-12-01
SK86788A3 (en)	2001-06-11
ATE96328T1 (de)	1993-11-15
FI880659L (fi)	1988-08-14
US5902587A (en)	1999-05-11
EP0285752A3 (en)	1990-01-03
HU201877B (en)	1991-01-28
YU26388A (en)	1989-10-31
SK281631B6 (sk)	2001-06-11
IE61572B1 (en)	1994-11-16
AR240401A1 (es)	1990-04-30
FI880659A0 (fi)	1988-02-12
DK73488A (da)	1988-08-14
NO174033B (no)	1993-11-29

Legal Events

Date	Code	Title	Description
1994-11-10	EP	Request for examination under paragraph 12(1) filed
1995-08-03	WP12	As result of examination under paragraph 12 erstrg. patent revoked

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