CN1433274A - Sweeteners pariticularly for coffee and tea - Google Patents
Sweeteners pariticularly for coffee and tea Download PDFInfo
- Publication number
- CN1433274A CN1433274A CN00818866A CN00818866A CN1433274A CN 1433274 A CN1433274 A CN 1433274A CN 00818866 A CN00818866 A CN 00818866A CN 00818866 A CN00818866 A CN 00818866A CN 1433274 A CN1433274 A CN 1433274A
- Authority
- CN
- China
- Prior art keywords
- carnitine
- salt
- cyclamate
- glucide
- agedoite
- 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.)
- Pending
Links
- 235000003599 food sweetener Nutrition 0.000 title claims abstract description 10
- 239000003765 sweetening agent Substances 0.000 title claims abstract description 10
- 241001122767 Theaceae Species 0.000 title claims abstract description 8
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims abstract description 16
- -1 alkanoyl L-carnitines Chemical class 0.000 claims abstract description 10
- 229940109275 cyclamate Drugs 0.000 claims description 15
- 235000005911 diet Nutrition 0.000 claims description 11
- 230000037213 diet Effects 0.000 claims description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 235000013361 beverage Nutrition 0.000 claims description 5
- 235000009508 confectionery Nutrition 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 4
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical class OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 235000021147 sweet food Nutrition 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 235000015203 fruit juice Nutrition 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 235000015243 ice cream Nutrition 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 235000014214 soft drink Nutrition 0.000 claims description 2
- 230000035922 thirst Effects 0.000 claims description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000605 aspartame Substances 0.000 abstract description 4
- 229960003438 aspartame Drugs 0.000 abstract description 4
- 108010011485 Aspartame Proteins 0.000 abstract description 3
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 abstract description 3
- 235000010357 aspartame Nutrition 0.000 abstract description 3
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 abstract 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 9
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 7
- 229960004203 carnitine Drugs 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000005257 alkyl acyl group Chemical group 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229960001948 caffeine Drugs 0.000 description 2
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 235000019605 sweet taste sensations Nutrition 0.000 description 2
- PIZNQHDTOZMVBH-UHFFFAOYSA-N thionylimide Chemical compound N=S=O PIZNQHDTOZMVBH-UHFFFAOYSA-N 0.000 description 2
- GADIJPCDIWZEMB-BTNVMJJCSA-N (2r,3r)-2,3-dihydroxybutanedioate;hydron;(3r)-3-hydroxy-4-(trimethylazaniumyl)butanoate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C[N+](C)(C)C[C@H](O)CC([O-])=O.C[N+](C)(C)C[C@H](O)CC([O-])=O GADIJPCDIWZEMB-BTNVMJJCSA-N 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- RZALONVQKUWRRY-FYZOBXCZSA-N 2,3-dihydroxybutanedioic acid;(3r)-3-hydroxy-4-(trimethylazaniumyl)butanoate Chemical compound OC(=O)C(O)C(O)C(O)=O.C[N+](C)(C)C[C@H](O)CC([O-])=O RZALONVQKUWRRY-FYZOBXCZSA-N 0.000 description 1
- PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010017577 Gait disturbance Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- BJZJDEOGMBZSLE-UHFFFAOYSA-N cyclohexane;hydrate Chemical compound O.C1CCCCC1 BJZJDEOGMBZSLE-UHFFFAOYSA-N 0.000 description 1
- MAJIZMVLTCWTKJ-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1.OS(=O)(=O)NC1CCCCC1 MAJIZMVLTCWTKJ-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 230000004129 fatty acid metabolism Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 235000015205 orange juice Nutrition 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- 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 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
- A23L27/30—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
Abstract
Salts of L-carnitine and lower alkanoyl L-carnitines with aspartame, cyclamic acid and saccharine are stable and non-hygroscopic and find utilization as sweeteners, particularly for coffee and tea.
Description
The present invention relates to the stable non-hydroscopic salts of L-carnitine and lower alkyl acyl-L-carnitine class, the sweetener that they self can be used as Food ﹠ Drink, particularly coffee ﹠ tea is used for the diet application.
Long ago can in cardiovascular field, be used for auxiliary such as for example treating acute and chronic myocardial ischaemia, angina pectoris, heart failure and ARR so different treatments application with regard to known carnitine and alkyl acyl derivative itself thereof.Acetyl group L-carnitine is used for the neurological field and treats central nervous system disorder and peripheral neurophaty, particularly diabetic peripheral neurophaty.Propiono L-carnitine is used for the treatment of chronic occlusion arteriosclerosis, particularly shows the patient's of serious wounded or disabled property sexual refractoriness limping symptom chronic occlusion arteriosclerosis.
On the other hand, carnitine and derivant thereof are tended to the extensively universal appearance rapidly of the application except the pure treatment that they once related to.
In fact, generally believed at professional athlete and be engaged among any experimenter of amateurish level of motion that the L-carnitine offers Musculoskeletal with energy and increases toleration to the strong anxiety that prolongs, improves the behavioral competence of this class individuality.
In addition, L (-)-carnitine or its low-grade alkane acidyl derivant have constituted two seed amino acids that diet has low carnitine content and low content and are the vegetarian of lysine and methionine (the biosynthetic precursor of L (-)-carnitine in kidney and the liver) and must depend on the requisite supplementary of those experimenters that lacks proteinic diet and survive for a long time.
Therefore, contain the carnitine or derivatives thereof and won the market of diet additive, health food, energy food and similar products at present as single component or with the various compositionss of the combination of other active component.
Long ago with regard to known L (-)-carnitine and alkyl acyl derivative thereof as by the inner salt (or " betaines ") of the following general formula representative moisture absorption and extremely unstable extremely when occurring:
Wherein R=H or C
1-C
5Low-grade alkane acidyl.
This result has produced the challenge of raw material and finished product processing, stability and storage aspect.For example, owing to L (-)-carnitine sheet must be packaged in the bubble-cap keeping their not ingresss of air, otherwise even having under the condition of normal humidity, they also can change, expand and become pasty state and become sticky.
Owing to knownly up to now be called (or " betaines ") L (-)-carnitine of so-called inner salt and the salt of alkyl acyl derivative exists identical treatment, nutrition or diet activity respectively, so the hygroscopicity problem of inner salt is by making itself and " pharmaceutically acceptable " can not have the sour salify of unwanted toxicity or side effect and temporarily obtain solution.
Lot of documents, particularly patent disclosure have been arranged the at present production method of the stable non-hydroscopic salts of this class.
In L-carnitine salt, have been found that up to now L-carnitine tartrate and L-carnitine acid fumarate have actual especially application.
Although above-mentioned " pharmaceutically acceptable " salt has more or less solved the hygroscopicity problem of L-carnitine inner satisfactorily, in known salt, do not have a kind of anionicsite to be endowed to change described salt on the whole over to or concur with the available and/or good to eat organoleptic attribute that improves the nutrition that may produce and/or positive effect by " carnitine " part of described salt itself (such as: sweet taste for example).
In addition, there is not a kind of acid that is used to produce non-hygroscopic L-carnitine salt can form the non-hydroscopic salts of alkanoyl L-carnitine.Therefore; for example; though L (-)-carnitine acid fumarate and L (-)-the carnitine tartrate is non-hygroscopic compound, and acetyl group L (-) carnitine acid fumarate and tartrate are respectively strong hygroscopic compounds, there be the shortcoming identical with corresponding inner salt in they.
The stable non-hydroscopic salts that the purpose of this invention is to provide L-carnitine and low-grade alkane acidyl L-carnitine, in addition, their stability and shortage hygroscopicity have also been protected the good to eat organoleptic attribute of the chemical compound that forms the anionicsite of described salt own.
Therefore, obviously, the application of finding salt of the present invention not only can have the hygroscopicity of shortage and advantages of higher stability with regard to its corresponding inner salt, and can be as general as described salt in its anion scope good to eat organoleptic attribute (particularly sweet taste) is provided.Therefore, the application of above-mentioned these new salts is not only to be produced by " carnitine " of described salt part.
Above-mentioned purpose by having following general formula the L-carnitine and the salt of alkanoyl L-carnitine obtain:
Wherein:
-R is hydrogen or the straight or branched alkanoyl that has 2-5 carbon atom; And
-A
-It is the monovalent anion that is selected from the group of agedoite salt (aspartamate), glucide hydrochlorate and cyclamate composition.
When R is alkanoyl, the group that it is preferably formed from acetyl group, propiono, bytyry, valeryl and isovaleryl.
The particularly preferred salt of the present invention is as follows:
-L-carnitine agedoite salt;
-L-carnitine cyclamate;
-L-carnitine glucide hydrochlorate;
-acetyl group L-carnitine agedoite salt;
-acetyl group L-carnitine cyclamate;
-acetyl group L-carnitine glucide hydrochlorate;
-propiono L-carnitine agedoite salt;
-propiono L-carnitine cyclamate;
-propiono L-carnitine glucide hydrochlorate;
-isovaleryl L-carnitine agedoite salt;
-isovaleryl L-carnitine cyclamate; With
-isovaleryl L-carnitine glucide hydrochlorate.
These chemical compounds can be as the such beverage of clabber for example, ice cream, sweet food, confection, diet, the sweetener and the diet additive of food.
In comprising coffee, tea, fruit juice, quenching one's thirst agent and general beverage such as such soft drink such as orange juice, Fructus Citri Limoniae juice, particularly advantageously available salt of the present invention, especially glucide hydrochlorate and the cyclamate with above-mentioned carnitine class increase sweet coffee and tea.
Glucide is generally as the non-heat sweetener of keeping low heat content diet.
The example that most typical glucide is used is the sweetener as coffee ﹠ tea.As known, these beverages contain a small amount of caffeine, and it is a kind of chemical compound that belongs to the big class material that is called methylxanthine.They can suppress phosphodiesterase that second message,second messenger cAMP is worked.Second message,second messenger cAMP is by being the adenylate cyclase enzymatic synthesis by generating the another kind of certain enzyme controlled such as the hormone that comprises epinephrine and sugar.
After the concentration of cAMP increases, many energy-producing systems have been stimulated.One of these processes are to discharge the steatolysis that takes place with the acid that contains in the fat.On the one hand, the caffeine of the enzyme of blocking-up degraded cAMP has prolonged its effect to energy-producing system, on the other hand, has promoted the optimum utilization produce power of fatty acid as known carnitine.Obtained dual function thus, promptly improved steatolysis and make and fat alleviate and avoided delaying of fatty acid metabolism.
Another advantage that salt of the present invention shows is its water solublity.
As known, glucide is slightly soluble in water: 1 gram is dissolved in 290mL water.Therefore, with regard to as with regard to the situation of sweetener, rely on the high energy of its sodium salt to reach 1 gram and be dissolved in 1.2mL water.
Similarly consider in fact water-fast cyclohexane sulfamic acid, and water-soluble fully as its sodium salt of sweetener.
Yet, the picked-up of sodium may to need sodium-restricted diet anyone be dangerous.
Obvious glucide hydrochlorate of the present invention and cyclamate have overcome above-mentioned defective.
Following non-limiting examples has been explained the preparation method and the physicochemical characteristic of some chemical compound of the present invention.
Embodiment 1
L-carnitine agedoite salt (BS/215)
The L-carnitine inner of 16.1g (0.1 mole) and N-L-α-aspartoyl L-phenyl-methyl lactamine (aspartame) of 29.4g (0.1 mole) are dissolved in 400mL water and the gained mixture is continued stirring 1 hour down at 40 ℃, till dissolving fully.
At room temperature from the solution that continue to stir, isolate dense condensed unbodied filterable hardly product, under 0 ℃ with its lyophilizing 2 days.
On the other hand, repeat identical step, but do not carry out lyophilizing, and concentrate amorphous and filterable hardly product in the vacuum under 40 ℃ and add isobutanol.Make the gained mixture carry out azeotropic distillation and with residue with acetone solution and filtration.
In two kinds of situations, all obtained the L-carnitine agedoite salt of 43g, for the powdered nonhygroscopic solid of a kind of white, productive rate is 95%; M.P.132-134 ℃ (decomposition).
Make the crystallization from dehydrated alcohol of thus obtained salt.
Elementary analysis: C
21H
34N
3O
8
C％
H％
N％
Value of calculation: 55.24 7.51 9.2
Measured value: 55.21 7.48 9.06
Light intensity: [a]
D 25=-10.5 (1%H
2O)
HPLC
L-carnitine: R
t=11.3
Aspartame: R
t=4.09 minutes
Post: SGE-SAX (5 μ m) 250 * 4mm
Temperature: 25 ℃
Eluant: KH
2PO
4/ CH
3CN (30-70) 0.05M
Flow velocity: 1mL/ minute
Ratio: L-carnitine-aspartame (35%-65%)
NMR?D
2O?δ＝7.4-7.3(3H，m，
)；7.3-7.2(2H，d，
)；4.5-4.6(1H，m，CHOH)；4.1-4.0(1H，m，CHNH
3)；3.3(3H，s，COOCH
3)；3.2-3.15(2H，d，CH
2N-)；3.2-3.1(1H，TCH-COO)；3.1-3.0(9H，s，(CH
3)
3N)；2.9-2.8(2H，m，
)；2.6-2.5(2H，m，CH
2-COO)；2.5-2.4(2H，d，CH
2-COO)
Embodiment 2
L-carnitine glucide hydrochlorate (BS/217)
With the 60mL dehydrated alcohol L-carnitine inner of 16.1g (0.1 mole) and the o-benzoic acid thionyl imide (glucide) of 18.3g (0.1 mole) were made the gained crystalline mixture 12 hours in dissolving under the heating condition and under room temperature and slow stirring condition.Sedimentary product filtered and under 30 ℃ very aerial thermostatic oven inner drying spend the night.
Obtained the L-carnitine glucide of 33g, for a kind of white non-hygroscopic crystalline solid.Productive rate is 95.5%.Very easily water-soluble.M.P.220 ℃ (decomposition).
Elementary analysis: C
14H
20N
2O
6S molecular weight: 344.38
C％ H％ N％ S％
Value of calculation: 48.8 5.8 8.1 9.3
Measured value: 48.56 6.26 8.01 9.22
H
2O content: 0.5%
pH：3.09?(1％H
2O)
[a]
D 25＝-13.3(c＝1％?H
2O)
HPLC
Post: SGE-SAX (5 μ m) 250 * 4mm
Temperature: 25 ℃
Eluant: CH
3CN/KH
2PO
450mM pH 5.5 70/30
Flow velocity: 0.1mL/ minute
O-benzoic acid thionyl imide (glucide) R
t=4.01 minutes.
L-carnitine R
t=11.303 minutes.
Ratio: L-carnitine-glucide (48%-52%)
NMR?D
2O?6＝7.9-7.8(2H，d，
)；7.8-7.7(2H，d，
)；4.7-4.6(1H，m，CHOH)；3.5-3.4(2H，d，NCH
2)；3.25-3.15(9H，s，(CH
3)
3N)；2.65-2.55(2H，d，CH
2COO)
Embodiment 3
Acetyl group L-carnitine glucide hydrochlorate (BS/218)
Under heating condition, 18.3g glucide (0.1 mole) is dissolved with 100mL ethanol.
The acetyl group L-carnitine inner that adds 20.3g (0.1 mole) under stirring condition in gained solution is till dissolving fully.At room temperature this solution is kept spending the night.From this solution, isolate white non-hygroscopic crystalline solid, it is filtered out and very aerial thermostatic oven inner drying under 40 ℃.
Obtained the acetyl group L-carnitine glucide hydrochlorate of 33g.Productive rate is 92%.M.P.154-156℃。
Elementary analysis: C
16H
22N
2O
7S molecular weight: 386.39
C％ H％ N％ S％
Value of calculation: 49.73 5.74 7.24 8.29
Measured value: 49.53 5.64 7.11 8.19
H
2O content: 0.63%
pH： 2.91(c＝1％H
2O)
[a]
D 25＝－15.2(c＝1％?H
2O)
HPLC
Post: SGE-SAX (5 μ m) 250 * 4mm
Temperature: 25 ℃
Eluant: CH
3CN/KH
2PO
450mM pH 5.5 70/30
Flow velocity: 0.1mL/ minute
Glucide R
t=4.01 minutes
Acetyl group L-carnitine Rt=8.98 minute
Ratio: glucide/acetyl-l-carnitine (48%-52%)
NMR?D
2O?6＝7.9-7.8(2H，d，
)；7.8-7.7(2H，d，
)；5.5-5.4
(1H，m，CH)；
3.8-3.5(2H，m，N-CH
2)；3.25-3.15(9H，s，(CH
3)
3N)；2.65-2.55
(2H，m，CH
2COO-)；2(2H，s，CO-CH
3)
Embodiment 4
L-carnitine cyclamate (BS/216)
With the 100mL isopropyl alcohol L-carnitine inner of 16.1g (0.1 mole) and the cyclohexyl sulfamic acid (cyclohexane sulfamic acid) of 17.9g (0.1 mole) are dissolved under heating condition.Make gained solution in room temperature and slowly crystallization 12 hours under the stirring condition.Be settled out solid, it is filtered out and under 30 ℃ very aerial thermostatic oven inner drying spend the night.
Obtained the L-carnitine cyclamate of 32g, for a kind of white non-hygroscopic crystalline solid.Productive rate is 95%.
Elementary analysis: C
12H
28N
2O
7S
C％ H％ N％ S％
Value of calculation: 45.8 8.3 8.29 9.4
Measured value: 46.01 8.61 8.12 9.32
H
2O content: 0.3%
pH：?3.1 (c＝1％?H
2O)
[a]
D 25＝-12.3 (c＝1％?H
2O)
M.P.:195 ℃ (decomposition)
HPLC
Post: SGE-SAX (5 μ m) 250 * 4mm
Temperature: 25 ℃
Eluant: CH
3CN/KH
2PO
450mM pH5.5 70/30
Flow velocity: 1.0mL/ minute
N-cyclohexyl sulfamic acid (N-cyclohexyilsulfamic acid) (cyclohexane sulfamic acid) R
t=4.37
L-carnitine Rt=11.303
Ratio: L-carnitine-cyclamate (47.5%-52.5%)
NMR?D
2O?δ＝4.6-4.5(2H，m，CHOH)；3.35-3.25(2H，d，CH
2-N)；
3.1-3.0(9H，s，(CH
2)
3N)；3.0-2.9(1H，m，CH)；2.5-2.4(2H，m，CH
2-COO)；
1.9-1.8(2H，m，
)；1.6-1.5(2H，m，
)；1.2-0.9(6H，m，
)
In following table 1, shown that making described chemical compound be exposed to 70 ± 5% relative humidity after 24 hours under 25 ℃ compare with the inner salt of L-carnitine and acetyl-l-carnitine, the weight of some chemical compound of the present invention increases (%) and outward appearance.
Table 1
Chemical compound
Weight increases %
Outward appearance
L-carnitine inner 21 deliquescence
Acetyl group L-carnitine inner 16 deliquescence
Embodiment 1 (BS/215) 0.31 does not have change
Embodiment 2 (BS/217) 0.27 does not have change
Embodiment 3 (BS/218) 0.29 does not have change
Embodiment 4 (BS/216) 0.23 does not have change
Claims (9)
1. the salt of the L-carnitine of following general formula or alkanoyl L-carnitine:
Wherein:
-R is hydrogen or the straight or branched alkanoyl that has carbon atom; And
-A-is the monovalent anion that is selected from the group of agedoite salt, glucide hydrochlorate and cyclamate composition.
2. the described salt of claim 1, wherein R is selected from the group that acetyl group, propiono, bytyry, valeryl and isovaleryl are formed.
3. claim 1 or 2 described salt, it is selected from the group that comprises following material:
-L-carnitine agedoite salt;
-L-carnitine cyclamate;
-L-carnitine glucide hydrochlorate;
-acetyl group L-carnitine agedoite salt;
-acetyl group L-carnitine cyclamate;
-acetyl group L-carnitine glucide hydrochlorate;
-propiono L-carnitine agedoite salt;
-propiono L-carnitine cyclamate;
-propiono L-carnitine glucide hydrochlorate;
-isovaleryl L-carnitine agedoite salt;
-isovaleryl L-carnitine cyclamate; With
-isovaleryl L-carnitine glucide hydrochlorate.
4. the sweetener that comprises at least a salt among the claim 1-3.
5. increase sweet beverage with at least a salt among the claim 1-3.
6. the described beverage of claim 5, it is selected from coffee, tea, fruit juice, agent and soft drink quench one's thirst.
7. increase sweet food with at least a salt among the claim 1-3.
8. the described food of claim 7, it is selected from clabber, ice cream, sweet food and confection.
9. increase sweet diet or diet additive with at least a salt among the claim 1-3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2000RM000185A IT1317013B1 (en) | 2000-04-12 | 2000-04-12 | SWEETENING SUBSTANCES, ESPECIALLY FOR COFFEE AND TEA. |
| ITRM2000A000185 | 2000-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1433274A true CN1433274A (en) | 2003-07-30 |
Family
ID=11454628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00818866A Pending CN1433274A (en) | 2000-04-12 | 2000-11-24 | Sweeteners pariticularly for coffee and tea |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1272057A1 (en) |
| CN (1) | CN1433274A (en) |
| AU (1) | AU2001218864A1 (en) |
| CA (1) | CA2404746A1 (en) |
| IT (1) | IT1317013B1 (en) |
| MX (1) | MXPA02010077A (en) |
| WO (1) | WO2001076393A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2425834A1 (en) * | 2010-09-06 | 2012-03-07 | Lonza Ltd. | Process for the production of l-carnitine tartrate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3463261D1 (en) * | 1983-12-28 | 1987-05-27 | Sigma Tau Ind Farmaceuti | Salts of l-carnitine and alkanoyl l-carnitines and process for preparing same |
| IT1209564B (en) * | 1984-06-29 | 1989-08-30 | Magis Farmaceutici | DERIVATIVES OF L-CARNITINE OR L-ACYL CARNITINE. |
| IT1289974B1 (en) * | 1997-02-25 | 1998-10-19 | Aldo Fassi | PROCESS FOR THE PRODUCTION OF STABLE AND NON-HYGROSCOPIC SALTS OF L (-) CARNITINE AND OF ALCANOLS L (-) - CARNITINE |
| CZ101297A3 (en) * | 1997-04-03 | 1998-10-14 | Nutrend, S.R.O. | Dietary complement from grain flakes |
| DE19817877C2 (en) * | 1998-04-22 | 2002-06-13 | Hans Guenter Berner | Energy drink based on fruit juice |
-
2000
- 2000-04-12 IT IT2000RM000185A patent/IT1317013B1/en active
- 2000-11-24 WO PCT/IT2000/000477 patent/WO2001076393A1/en not_active Application Discontinuation
- 2000-11-24 MX MXPA02010077A patent/MXPA02010077A/en unknown
- 2000-11-24 AU AU2001218864A patent/AU2001218864A1/en not_active Abandoned
- 2000-11-24 EP EP00981642A patent/EP1272057A1/en not_active Withdrawn
- 2000-11-24 CA CA002404746A patent/CA2404746A1/en not_active Abandoned
- 2000-11-24 CN CN00818866A patent/CN1433274A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA02010077A (en) | 2003-09-10 |
| EP1272057A1 (en) | 2003-01-08 |
| ITRM20000185A1 (en) | 2001-10-12 |
| CA2404746A1 (en) | 2001-10-18 |
| AU2001218864A1 (en) | 2001-10-23 |
| WO2001076393A1 (en) | 2001-10-18 |
| ITRM20000185A0 (en) | 2000-04-12 |
| IT1317013B1 (en) | 2003-05-26 |
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