GB875713A - Polyene carboxylic acids and esters thereof and a process for the manufacture of same - Google Patents
Polyene carboxylic acids and esters thereof and a process for the manufacture of sameInfo
- Publication number
- GB875713A GB875713A GB27596/58A GB2759658A GB875713A GB 875713 A GB875713 A GB 875713A GB 27596/58 A GB27596/58 A GB 27596/58A GB 2759658 A GB2759658 A GB 2759658A GB 875713 A GB875713 A GB 875713A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- compounds
- methoxycarbonyl
- manufacture
- acid
- Prior art date
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/47—Addition of dyes or pigments, e.g. in combination with optical brighteners using synthetic organic dyes or pigments not covered by groups A23L5/43 - A23L5/46
Landscapes
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of formula I wherein n = O, and a process for the manufacture of compounds of formula I wherein n is 0, 1, 2 or 3 and R (reading from left to right) is the methyl group and is only present in the parenthetical fragments corresponding to the first and third extensions of the chain. <FORM:0875713/IV (b)/1> by converting the phosphonium salt (II) into the corresponding phosphorane, condensing the latter with Vitamin A aldehyde, splitting off triaryl-phosphine oxide from the so formed adduct (e.g. by heating) and, if required, hydrolysing the ester obtained. Such compounds (I) are used as additives for poultry feeds for pigmentation of the egg yolk, circulation, beak, skin, fat and flesh. <FORM:0875713/IV (b)/2> The phosphonium salts (II) may be obtained by condensation of halogenocarboxylic esters, e.g. an a -haloacetic acid ester or a g -halotiglinic acid ester, with a triaryl phosphine in an inert solvent, e.g. benzene. Two suitable halogenoesters are stated to be novel and may be prepared as follows. Reaction of methyl b -acetylacrylate with lithium acetylide and hydrogenation of the product (after decomposition with ammonium chloride) with Pb-inhibited Pd catalyst gives 1-methoxycarbonyl-3-methyl - 3 - hydroxypentadiene-(1:4), which with PBr3 gives 1-methoxycarbonyl-3-methyl-5-bromopentadiene-(1:3); hydrogenation p (same catalyst) of the tetrahydropyranyl ether of the said pentadiene-(1:4) derivative in presence of quinoline and reduction of the product with LiAlH4, followed by oxidation with MnO2 in petroleum ether, gives 4-methyl-4-(tetrahydro-pyranyloxy) - hexadiene - (2:5) - al - 1, which affords 1 - methoxycarbonyl - 1:5 - dimethyl-7-bromoheptatriene-(1:3:5) by reaction with (1-methoxycarbonylethylidene) - triphenyl phosphorane followed by hydrobromic acid. Examples are given of the production of 2,6,11,15 - tetramethyl - 17 - [21,61,61-trimethyl-cyclohexen -1-yl]-heptadecaoctaen-(2,4,6,8,10,12, 14,16)-oic-1 acid methyl ester and 5,9-dimethyl-11 - [21,61, 61-trimethylcyclohexen-1-yl]-undecapentaene-(2,4,6,8,10) -oic-1-acid methyl ester by reacting [3 - methyl-7-methoxycarbonyl-octatriene - (2,4,6) - ylidene]-triphenyl phosphorane and methoxycarbonylmethylene-triphenyl phosphorane respectively with Vitamin-A aldehyde. The hydrolysis of the product of the first example to the corresponding acid is also described.ALSO:The invention comprises a process for the manufacture of compounds of the formula indicated, wherein n is 0, 1, 2 or 3 and R (reading from left to right) is the methyl group and is only present in the parenthetical fragments corresponding to the first and third extensions of the chain, (see Group IV(b)). <FORM:0875713/I/1> The compounds are useful as additives for poultry feeds for pigmentation of the egg yolk, circulation, beak, skin, fat and flesh.ALSO:The invention comprises a process for the manufacture of compounds of the formula indicated, wherein n is 0, 1, 2 or 3 and R (reading from left to right) is the methyl group and is only present in the parenthetical fragments corresponding to the first and third extensions of the chain (see Group IV (b)) <FORM:0875713/VI/1> The compounds are useful as colouring materials for foodstuffs.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB27596/58A GB875713A (en) | 1958-08-28 | 1958-08-28 | Polyene carboxylic acids and esters thereof and a process for the manufacture of same |
CH7572159A CH382148A (en) | 1958-08-28 | 1959-07-14 | Process for the preparation of polyenecarboxylic acid esters |
BE582042A BE582042A (en) | 1958-08-28 | 1959-08-26 | Process for the preparation of polyenecarboxylic esters and their saponification products |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB27596/58A GB875713A (en) | 1958-08-28 | 1958-08-28 | Polyene carboxylic acids and esters thereof and a process for the manufacture of same |
Publications (1)
Publication Number | Publication Date |
---|---|
GB875713A true GB875713A (en) | 1961-08-23 |
Family
ID=10262200
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB27596/58A Expired GB875713A (en) | 1958-08-28 | 1958-08-28 | Polyene carboxylic acids and esters thereof and a process for the manufacture of same |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE582042A (en) |
CH (1) | CH382148A (en) |
GB (1) | GB875713A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3443627A1 (en) * | 1984-11-29 | 1986-05-28 | USV Pharmaceutical Corp., Tuckahoe, N.Y. | Polyolefinic alpha -alkylcarboxylic acids and their derivatives, and pharmaceuticals containing these compounds |
US4694023A (en) * | 1982-06-28 | 1987-09-15 | Usv Pharmaceutical Corporation | Alpha-alkyl polyolefinic carboxylic acids and derivatives thereof useful in the treatment of psoriasis and allergic responses |
-
1958
- 1958-08-28 GB GB27596/58A patent/GB875713A/en not_active Expired
-
1959
- 1959-07-14 CH CH7572159A patent/CH382148A/en unknown
- 1959-08-26 BE BE582042A patent/BE582042A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4694023A (en) * | 1982-06-28 | 1987-09-15 | Usv Pharmaceutical Corporation | Alpha-alkyl polyolefinic carboxylic acids and derivatives thereof useful in the treatment of psoriasis and allergic responses |
DE3443627A1 (en) * | 1984-11-29 | 1986-05-28 | USV Pharmaceutical Corp., Tuckahoe, N.Y. | Polyolefinic alpha -alkylcarboxylic acids and their derivatives, and pharmaceuticals containing these compounds |
Also Published As
Publication number | Publication date |
---|---|
CH382148A (en) | 1964-09-30 |
BE582042A (en) | 1960-02-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3523138A (en) | Treatment of marigold petal meal to obtain a xanthophyll product | |
Gensler et al. | Synthesis of Unsaturated Fatty Acids: Linoleic Acid | |
GB875713A (en) | Polyene carboxylic acids and esters thereof and a process for the manufacture of same | |
DE717652C (en) | Process for the production of acetoacetic esters | |
GB592827A (en) | Improvements in or relating to the manufacture of phenoxyalkylcarboxylic compounds | |
Kohda et al. | Total synthesis of (S)-(+)-solanone | |
IL58963A (en) | Production of optically active derivatives of cyclopropanecarboxylic acid and novel cyclobutane sulfonic acid derivatives used therefor | |
Elion et al. | Synthesis of 8-C14 and of S35-6-Mercaptopurine | |
US2260800A (en) | Process of making tertiary butyl malonic acid | |
Jones et al. | 302. Reformatsky reactions with methyl γ-bromocrotonate | |
SU48295A1 (en) | The method of obtaining veratraldehyde | |
US2802871A (en) | Preparation of disulfides of hydroxy butyric acid and derivatives thereof | |
GB567682A (en) | Process for preparing carotenoid concentrates from palm oil | |
GB341158A (en) | Improvements in the manufacture and production of esters | |
US3304333A (en) | Polyene-1-ols insect attractants | |
US3014053A (en) | Process for producing derivatives of vitamin a aldehyde and products thereof | |
GB418723A (en) | A manufacture of primary diterpene-alcohols | |
US1663817A (en) | Process for the manufacture of farnesol | |
JPS6152184B2 (en) | ||
GB644406A (en) | Improvements in or relating to the dehydration of hydroxylated fatty acid esters | |
SU503572A1 (en) | Juvenile hormone-like insecticide | |
SU98997A1 (en) | The method of accelerated polymerization of vegetable oils | |
GB850137A (en) | A process for the manufacture of polyene carboxylic acids and esters thereof and novel polyene carboxylic acids and esters thereof | |
SU108897A1 (en) | Method for preparing 4-nitroso-5-nitro-1-naphthol | |
GB404520A (en) | Derivatives of the di-hydroxy-benzenes and process for the manufacture of same |