GB1034352A - Unsaturated aldehydes and their use in flavouring food - Google Patents

Unsaturated aldehydes and their use in flavouring food

Info

Publication number
GB1034352A
GB1034352A GB32360/62A GB3236062A GB1034352A GB 1034352 A GB1034352 A GB 1034352A GB 32360/62 A GB32360/62 A GB 32360/62A GB 3236062 A GB3236062 A GB 3236062A GB 1034352 A GB1034352 A GB 1034352A
Authority
GB
United Kingdom
Prior art keywords
diyne
give
reacted
catalyst
trienal
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
Application number
GB32360/62A
Inventor
David Adrian Van Dorp
Philip Akroyd
Lothar Mindt
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.)
Unilever PLC
Original Assignee
Unilever PLC
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.)
Filing date
Publication date
Application filed by Unilever PLC filed Critical Unilever PLC
Priority to LU44297D priority Critical patent/LU44297A1/xx
Priority to NL63296925A priority patent/NL139102B/en
Priority to DK400363AA priority patent/DK112420B/en
Priority to DE1517129A priority patent/DE1517129C3/en
Priority to AT678563A priority patent/AT264996B/en
Priority to CH1040763A priority patent/CH471545A/en
Priority to IT17488/63A priority patent/IT1061785B/en
Priority to SE9224/63A priority patent/SE316359B/xx
Publication of GB1034352A publication Critical patent/GB1034352A/en
Priority to US28215A priority patent/US3686003A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/12—Straight chain carboxylic acids containing eighteen carbon atoms
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Seasonings (AREA)

Abstract

Hept-1-yne is prepared from sodium acetylide and amyl bromide Deca 1,4-diyne is prepared by treatment of the Grignard derivative of hept-1-yne with propargyl bromide in the presence of cuprous chloride. 2 - Methyltetradeca - 5,8 - diyne - 2 - ene is prepared by treatment of the Grignard derivative of deca-1,4-diyne with 1-bromo-3-methylbutene-2 in the presence of cuprous cyanide.ALSO:The invention comprises undeca-2,5-dienal; dodeca - 3,6 - dienal; trideca - 4,7 - dienal; trideca - 2,4,7 - trienal; tetradeca - 2,4,8-trienal; tetradeca - 2,5,8 - trienal; pentadeca-3,6,9 - trienal; hexadeca - 4,7,10 - trienal; hexadeca - 2,4,7,10 - tetraenal; heptadeca-2,5,8,11-tetraenal. The aldehydes of the invention and other C11 to C17 aliphatic aldehydes containing 2 to 4 olefinic bonds may be prepared by oxidation of the corresponding alcohols, by hydrolysis of the corresponding acetals, hemiacetals and the esters of the hypothetical gem diols corresponding to the aldehydes, or by autoxidation of compounds, preferably carboxylic acids or functional derivatives thereof, containing the grouping C5H11-(CH = CH-CH2)nC wherein n is 3 or 4. The oxidations may be effected in the presence of an oxidation catalyst, preferably chlorophyll. The bisulphate addition compounds of said C11 to C17 aldehydes can be obtained by oxidation or autoxidation, in the presence or absence of a catalyst, of a precursor, followed by treatment with the bisulphite of an alkali metal or by addition of a solution of SO2 in water to or passage of gaseous SO2 through the reaction mixture during said oxidation. In Example 1, hept-1-yne in the form of its Grignard derivative was treated with proparyl bromide in the presence of cuprous chloride to form deca-1,4-diyne, which as its Grignard derivative was reacted with orthoformic ester to give 1,1-diethoxyundeca-2,5-diyne, which was hydrogenated over Lindlar's catalyst to 1,1-diethoxyundeca-2,5-diene. In Example 2, 2,3-dibromopropanol was reacted with orthoformic ester to give 1,1-diethoxy - 2,3 - dibromopropane, which on dehydrobromination with sodamide in liquid ammonia gives 1,1-diethoxyprop-2-yne, which as its Grignard is reacted with propargyl bromide in the presence of cuprous chloride to give 1,1-diethoxyhexa-2,5-diyne. In Example 3, 1,1-diethoxyhexa-2,5-diyne as its Grignard derivative was reacted with oct-2-yne bromide in the presence of cuprous chloride to give 1,1-diethoxytetra-2,5,8-triyne, which was hydrogenated over a Lindlar's catalyst to give 1,1-diethoxytetra-2,5,8-triene. In Example 4, 1,1-diethoxyhexa-2,5-diyne was treated with ethyl magnesium bromide to form the Grignard derivative, which was reacted with 1-bromo-undeca-2,5-diyne in the presence of cuprous chloride to form 1,1-diethoxyheptadeca - 2,5,8,11 - tetrayne, this was hydrogenated over Lindlar's catalyst to 1,1-diethoxyheptadeca-2,5,8,11-tetraene. In Example 5, deca-1,4-diyne as its Grignard derivative was reacted with 1-bromo-3-methylbutene-2 in the presence of cuprous cyanide to give 2-methyltetradeca-5,8-diyne-2-ene, which was treated with perbenzoic acid and the epoxy compound so formed was decomposed to give 2 - methyltetradeca - 5,8 - diyne - 2,3 - diol, which was then hydrogenated over a Lindlar's catalyst to give 2-methyltetradeca-5,8-diene-2,3-diol.
GB32360/62A 1962-08-23 1962-08-23 Unsaturated aldehydes and their use in flavouring food Expired GB1034352A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
LU44297D LU44297A1 (en) 1962-08-23 1963-08-20
NL63296925A NL139102B (en) 1962-08-23 1963-08-21 METHOD FOR AROMATIZING FOODS.
DK400363AA DK112420B (en) 1962-08-23 1963-08-21 Flavor and flavor enhancer and process for preparing the composition from a precursor.
DE1517129A DE1517129C3 (en) 1962-08-23 1963-08-22 Process for flavoring food
AT678563A AT264996B (en) 1962-08-23 1963-08-23 Process for flavoring food
CH1040763A CH471545A (en) 1962-08-23 1963-08-23 Process for flavoring food and flavoring agents for carrying out this process
IT17488/63A IT1061785B (en) 1962-08-23 1963-08-23 METHOD FOR TASTING FOOD PRODUCTS BY ADDING ALIPHATIC ALDEHYDES
SE9224/63A SE316359B (en) 1962-08-23 1963-08-23
US28215A US3686003A (en) 1962-08-23 1970-04-15 Flavoring foods by addition of unsaturated aliphatic aldehydes or precursors thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU44297 1963-08-20

Publications (1)

Publication Number Publication Date
GB1034352A true GB1034352A (en) 1966-06-29

Family

ID=19723484

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32360/62A Expired GB1034352A (en) 1962-08-23 1962-08-23 Unsaturated aldehydes and their use in flavouring food

Country Status (3)

Country Link
BE (1) BE656141A (en)
ES (1) ES306574A3 (en)
GB (1) GB1034352A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2020643A1 (en) * 1968-10-14 1970-07-17 Unilever Nv
EP0173395A1 (en) * 1984-08-23 1986-03-05 Naarden International N.V. Perfume compositions and perfumed products which contain one or more 4,7-alkadienals as the essential substance
JP2014043409A (en) * 2012-08-27 2014-03-13 T Hasegawa Co Ltd Flavor imparting or promoting agent
US20140120232A1 (en) * 2011-07-15 2014-05-01 T. Hasegawa Co., Ltd. Acid taste/acid smell-reducing agent
JP2016124833A (en) * 2015-01-05 2016-07-11 高田香料株式会社 2(e),8(z)-tetradecadiene-1-al and perfume composition containing the same

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2020643A1 (en) * 1968-10-14 1970-07-17 Unilever Nv
EP0173395A1 (en) * 1984-08-23 1986-03-05 Naarden International N.V. Perfume compositions and perfumed products which contain one or more 4,7-alkadienals as the essential substance
US4687599A (en) * 1984-08-23 1987-08-18 Naarden International N.V. Perfume compositions and perfumed products which contain one or more 4,7-alkadienals as the essential substance
US20140120232A1 (en) * 2011-07-15 2014-05-01 T. Hasegawa Co., Ltd. Acid taste/acid smell-reducing agent
JP2014043409A (en) * 2012-08-27 2014-03-13 T Hasegawa Co Ltd Flavor imparting or promoting agent
JP2016124833A (en) * 2015-01-05 2016-07-11 高田香料株式会社 2(e),8(z)-tetradecadiene-1-al and perfume composition containing the same

Also Published As

Publication number Publication date
ES306574A3 (en) 1965-05-01
BE656141A (en) 1965-05-24

Similar Documents

Publication Publication Date Title
Payne Epoxide migrations with α, β-epoxy alcohols
Lloyd et al. Oxidations of olefins with alcoholic palladium (II) salts
Ishmuratov et al. Transformations of peroxide products of olefins ozonolysis
Hegde et al. The reaction of hypochlorous acid with olefins. A convenient synthesis of allylic chlorides
GB1034352A (en) Unsaturated aldehydes and their use in flavouring food
US2428590A (en) Production of allyl type compounds
BR112019002053B1 (en) COMPOUND, METHODS FOR PREPARING COMPOUNDS AND FOR TRANSMITTING AND/OR INTENSIFYING AN ODOR OR FLAVOR OF A PRODUCT, USE OF A COMPOUND, FLAVORING COMPOSITION, AND, FRAGRANCE OR FLAVORING PRODUCT
US3686003A (en) Flavoring foods by addition of unsaturated aliphatic aldehydes or precursors thereof
Ege et al. Synthesis of methyl 5, 8, 11, 14-eicosatetraenoate (methyl arachidonate)
GB1182212A (en) Polyenic Alcohols, Aldehydes and Acids
Greene et al. Cyclic Diacyl Peroxides. V. 1 Reaction of Phthaloyl Peroxide with Norbornylene
Pryde et al. Unsaturated aldehyde oils by the partial ozonization of soybean oil
GB1049421A (en) Improvements in or relating to ª‰,ª†-unsaturated aliphatic aldehydes
US3773842A (en) Process for the preparation of 1,2,6-hexanetriol
Mager et al. Synthesis of fluoropyruvic acid and some of its biological properties
GB1059675A (en) Novel unsaturated aldehydes
US4017527A (en) Metallic-organo-peroxide and organo-metallic-peroxide
US3257448A (en) Preparation of saturated esters by oxidation of aldehydes with a palladium salt, a redox system and molecular oxygen in alcoholic medium
JPS6212735A (en) (2z,4e(or 4z))-2,4,11-dodecatrienal and perfumery composition containing same
HURD et al. The Action of Lead Tetraacetate on Dihydropyran
GB1414323A (en) Preparation of fluorinated aldehydes and alcohols
Shine et al. THE DECOMPOSITION OF ACETYL PEROXIDE: THE EFFECT OF IODINE
US2600054A (en) Process for preparing esters
Ishmuratov et al. Use of enyne compounds in the synthesis of insect pheromones
US2797234A (en) Tertiary carbinyl esters and their preparation