CH370402A - Verfahren zur Herstellung von Estern des 4,4'-Dihydroxy-ss-carotins - Google Patents

Verfahren zur Herstellung von Estern des 4,4'-Dihydroxy-ss-carotins

Info

Publication number: CH370402A
Authority: CH; Switzerland
Prior art keywords: carotene; dihydroxy; solvent; esters; acid
Prior art date: 1958-01-20

Application number

CH5483858A

Other languages

German (de)

English (en)

Inventor

Paul Dr Karrer

Roland Dr Entschel

Original Assignee

Hoffmann La Roche

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.)

1958-01-20

Filing date

1958-01-20

Publication date

1963-07-15

1958-01-20 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1958-01-20 Priority to CH5483858A priority Critical patent/CH370402A/de

1959-01-13 Priority to BE574701A priority patent/BE574701A/fr

1963-07-15 Publication of CH370402A publication Critical patent/CH370402A/de

Links

238000000034 method Methods 0.000 title claims description 13
239000011648 beta-carotene Substances 0.000 title claims description 10
229960002747 betacarotene Drugs 0.000 title claims description 10
150000002148 esters Chemical class 0.000 title claims description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
OENHQHLEOONYIE-UKMVMLAPSA-N beta-Carotene Chemical compound CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 claims description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 4
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 3
TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 claims description 3
235000013734 beta-carotene Nutrition 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
235000019260 propionic acid Nutrition 0.000 claims description 3
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
150000007530 organic bases Chemical group 0.000 claims 3
150000001721 carbon Chemical class 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
239000003495 polar organic solvent Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002585 base Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 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
235000011054 acetic acid Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH5483858A 1958-01-20 1958-01-20 Verfahren zur Herstellung von Estern des 4,4'-Dihydroxy-ss-carotins CH370402A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH5483858A CH370402A (de)	1958-01-20	1958-01-20	Verfahren zur Herstellung von Estern des 4,4'-Dihydroxy-ss-carotins
BE574701A BE574701A (fr)	1958-01-20	1959-01-13	Procédé pour la préparation de composés dihydroxycaroténiques et de leurs produits d'estérification

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH5483858A CH370402A (de)	1958-01-20	1958-01-20	Verfahren zur Herstellung von Estern des 4,4'-Dihydroxy-ss-carotins

Publications (1)

Publication Number	Publication Date
CH370402A true CH370402A (de)	1963-07-15

Family

ID=4519478

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5483858A CH370402A (de)	1958-01-20	1958-01-20	Verfahren zur Herstellung von Estern des 4,4'-Dihydroxy-ss-carotins

Country Status (2)

Country	Link
BE (1)	BE574701A (fr)
CH (1)	CH370402A (fr)

1958
- 1958-01-20 CH CH5483858A patent/CH370402A/de unknown
1959
- 1959-01-13 BE BE574701A patent/BE574701A/fr unknown

Also Published As

Publication number	Publication date
BE574701A (fr)	1959-07-13

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