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WO2001076393A1 - Edulcorants destines notamment au the et au cafe - Google Patents

Edulcorants destines notamment au the et au cafe Download PDF

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Publication number
WO2001076393A1
WO2001076393A1 PCT/IT2000/000477 IT0000477W WO0176393A1 WO 2001076393 A1 WO2001076393 A1 WO 2001076393A1 IT 0000477 W IT0000477 W IT 0000477W WO 0176393 A1 WO0176393 A1 WO 0176393A1
Authority
WO
WIPO (PCT)
Prior art keywords
carnitine
salt
saccharinate
cyclamate
acetyl
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.)
Ceased
Application number
PCT/IT2000/000477
Other languages
English (en)
Inventor
Antonietta Buononato
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.)
Biosalts Srl
Original Assignee
Biosalts Srl
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 Biosalts Srl filed Critical Biosalts Srl
Priority to AU2001218864A priority Critical patent/AU2001218864A1/en
Priority to EP00981642A priority patent/EP1272057A1/fr
Priority to MXPA02010077A priority patent/MXPA02010077A/es
Priority to CA002404746A priority patent/CA2404746A1/fr
Publication of WO2001076393A1 publication Critical patent/WO2001076393A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
    • C07K5/0613—Aspartame

Definitions

  • Sweeteners particularly for coffee and tea
  • the present invention relates to stable, non-hygroscopic salts of L- carnitine and lower alkanoyl L-carnitines which lend themselves to alimentary utilization as sweeteners for foodstuffs and beverages, particularly coffee and tea.
  • carnitine and its alkanoyl derivatives lend themselves to various therapeutical utilizations such as e.g. in the cardiovascular field for the treatment of acute and chronic myocardial ischaemia, angina pectoris, heart failure and cardiac arrhythmias.
  • Acetyl L-carnitine is used in the neurologic field for the treatment of both central nervous system disturbances and peripheral neuropathies, particularly diabetic peripheral neuropathy.
  • Propionyl L-carnitine is used for the treatment of chronic arteriosclerosis obliterans, particularly in patients showing the symptom of severely disabling intermittent claudication.
  • L-carnitine supplies energy to the skeletal musculature and increases the resistance to prolonged, intense stress, enhancing the performance capability of such individuals.
  • L(-) -carnitine or its lower alkanoyl derivatives constitute indispensable nutritional supplements for both vegetarians, whose diets have a low carnitine content as well as a low content of the two amino acids, lysine and methionine (the precursors of the biosynthesis of L(-)-carnitine in the kidneys and liver) and those subjects who have to live on a diet poor in protein for prolonged periods of time. Consequently, various compositions containing carnitine or derivatives thereof, either as single components or in combinations with further active ingredients, have recently reached the market of the dietary supplements, health foods, energy foods and similar products.
  • L(-)-carnitine tablets have to be packaged in blisters to keep them out of contact with the air, since, otherwise, even in the presence of normal humidity conditions, they would undergo alterations, swelling up and becoming pasty and sticky.
  • L-carnitine salts particularly L-carnitine tartrate and L- carnitine acid fumarate have to-date found practical utilization.
  • the aforesaid "pharmacologically acceptable" salts solve the problem of the hygroscopicity of L-carnitine inner salt more or less satisfactorily, in none of the known salts the anion moiety as endowed with useful and or palatable organoleptic properties (such as e. g., the sweet taste) which are transferred to the salt as a whole or co-operates to enhance the nutritional and/or energetic efficacy which can be attributed to the "carnitine" moiety of the salts themselves.
  • none of the acids used for producing non-hygroscopic L- carnitine salts is capable of forming non-hygroscopic salts of alkanoyl L-carnitine.
  • L(-) -carnitine acid fumarate and L(-) -carnitine tartrate are non-hygroscopic compounds
  • acetyl L(-)- carnitine acid fumarate and tartrate are strongly hygroscopic compounds, which present the same drawbacks as the corresponding inner salt.
  • the object of the present invention is to provide stable, non-hygroscopic salts of L-carnitine and lower alkanoyl L-carnitine which in addition their stability and lack of hygroscopicity preserve the palatable organoleptic properties of the compounds which form the anionic moiety of the salts themselves.
  • the utility of the salts of the present invention is to be found not only in their lack of hygroscopicity and higher stability with respect to their corresponding inner salts but also insofar as their anion moiety provides palatable organoleptic properties (specifically the sweet taste) to the salts as a whole.
  • the aforesaid utility of these novel salts is, therefore, not to be attributed exclusively to the "carnitine" moiety of the salt.
  • R is hydrogen or a straight or branched-chain alkanoyl group having 2-5 carbon atoms
  • A" is a monovalent anion selected from the group consisting of aspartamate, saccharinate and cyclamate.
  • R is an alkanoyl group, it is preferably selected from the group consisting of acetyl, propionyl, butyryl, valeryl and isovaleryl.
  • L-carnitine saccharinate acetyl L-carnitine aspartamate; acetyl L-carnitine cyclamate; acetyl L-carnitine saccharinate; propionyl L-carnitine aspartamate; propionyl L-carnitine cyclamate; propionyl L-carnitine saccharinate; isovaleryl L-carnitine aspartamate; isovaleryl L-carnitine cyclamate; and isovaleryl L-carnitine saccharinate.
  • sweeteners for drinks, foodstuffs, e.g. yoghurt, ice-creams, sweets, candies, dietary and dietetic supplements.
  • beverages which comprise coffee, tea, fruit juices, thirst- quenchers and soft drinks in general such as orange juices, lemonades and the like, particularly coffee and tea can be advantageously sweetened with the salts of the present invention, especially with the saccharinates and cyclamates of the aforesaid carnitines.
  • Saccharine is generally used as a non-caloric sweetener which contributes to maintenance of hypocaloric diets.
  • saccharine utilization is as coffee and tea sweetener.
  • these beverages contain small amounts of caffeine, a compound belonging to a wide class of substances known as methylxanthines. These are able to inhibit the enzymes phospho- diesterases which are active on the second messanger cAMP. This is synthesized by another specific enzyme, adenyl cyclase, which is controlled by hormones such as, among others, adrenaline and glucogenasis.
  • a further advantage shown by the salts of the present invention is their water-solubility.
  • saccharine is slightly soluble in water: one gram dissolves in 290 mL water. Consequently, for use as a sweetener its sodium salt is resorted to, one gram of which dissolves in 1.2 L water only. Similar considerations hold for cyclamic acid which is practically insoluble in water, whereas its sodium salt which is used as sweetener, is completely water-soluble.
  • sodium intake may be dangerous to anybody in need of a sodium-restricted diet.
  • the salt thus obtained was crystallized from absolute ethanol.
  • Acetyl L-carnitine inner salt 16 deliquescent

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Food Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Nutrition Science (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des sels de L-carnitine et de L-carnitines alcanoyles inférieurs stables et non hygroscopiques avec l'aspartame, l'acide cyclamique et la saccharine, s'utilisant comme édulcorants, notamment pour le thé et le café.
PCT/IT2000/000477 2000-04-12 2000-11-24 Edulcorants destines notamment au the et au cafe Ceased WO2001076393A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU2001218864A AU2001218864A1 (en) 2000-04-12 2000-11-24 Sweeteners, particularly for coffee and tea
EP00981642A EP1272057A1 (fr) 2000-04-12 2000-11-24 Edulcorants destines notamment au the et au cafe
MXPA02010077A MXPA02010077A (es) 2000-04-12 2000-11-24 Edulcorantes, particularmente para cafe y te.
CA002404746A CA2404746A1 (fr) 2000-04-12 2000-11-24 Edulcorants destines notamment au the et au cafe

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2000RM000185A IT1317013B1 (it) 2000-04-12 2000-04-12 Sostanze dolcificanti, particolarmente per il caffe' ed il the'.
ITRM2000A000185 2000-04-12

Publications (1)

Publication Number Publication Date
WO2001076393A1 true WO2001076393A1 (fr) 2001-10-18

Family

ID=11454628

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IT2000/000477 Ceased WO2001076393A1 (fr) 2000-04-12 2000-11-24 Edulcorants destines notamment au the et au cafe

Country Status (7)

Country Link
EP (1) EP1272057A1 (fr)
CN (1) CN1433274A (fr)
AU (1) AU2001218864A1 (fr)
CA (1) CA2404746A1 (fr)
IT (1) IT1317013B1 (fr)
MX (1) MXPA02010077A (fr)
WO (1) WO2001076393A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120059189A1 (en) * 2010-09-06 2012-03-08 Thomas Buechner Process for the production of l-carnitine tartrate

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0150688A1 (fr) * 1983-12-28 1985-08-07 Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. Sels de L-carnitine et d'alcanoyl L-carnitines et procédé pour leur préparation
EP0167115A2 (fr) * 1984-06-29 1986-01-08 Magis Farmaceutici S.P.A. Dérivés de la L-carnitine
DE29805782U1 (de) * 1997-04-03 1998-07-30 NUTREND, s.r.o., Olomouc Diätische Nahrungsergänzung aus Getreideflocken
WO1998038157A1 (fr) * 1997-02-25 1998-09-03 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Procede pour la preparation de sels non hygroscopiques stables de l (-)carnitine et d'alcanoyle l (-)carnitines
EP0951844A2 (fr) * 1998-04-22 1999-10-27 Hans-Günter Berner Boisson énergétique à base de jus de fruits

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0150688A1 (fr) * 1983-12-28 1985-08-07 Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. Sels de L-carnitine et d'alcanoyl L-carnitines et procédé pour leur préparation
EP0167115A2 (fr) * 1984-06-29 1986-01-08 Magis Farmaceutici S.P.A. Dérivés de la L-carnitine
WO1998038157A1 (fr) * 1997-02-25 1998-09-03 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Procede pour la preparation de sels non hygroscopiques stables de l (-)carnitine et d'alcanoyle l (-)carnitines
DE29805782U1 (de) * 1997-04-03 1998-07-30 NUTREND, s.r.o., Olomouc Diätische Nahrungsergänzung aus Getreideflocken
EP0951844A2 (fr) * 1998-04-22 1999-10-27 Hans-Günter Berner Boisson énergétique à base de jus de fruits

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120059189A1 (en) * 2010-09-06 2012-03-08 Thomas Buechner Process for the production of l-carnitine tartrate
US8779188B2 (en) * 2010-09-06 2014-07-15 Lonza Ltd. Process for the production of L-carnitine tartrate

Also Published As

Publication number Publication date
CA2404746A1 (fr) 2001-10-18
MXPA02010077A (es) 2003-09-10
ITRM20000185A1 (it) 2001-10-12
IT1317013B1 (it) 2003-05-26
ITRM20000185A0 (it) 2000-04-12
AU2001218864A1 (en) 2001-10-23
EP1272057A1 (fr) 2003-01-08
CN1433274A (zh) 2003-07-30

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