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Betain
TRIMETHYLGLYCINE · Glycine betaine · Betain · BET · Abromine · Methanaminium · ANHYDROUS BETAINE · LYCINE
Identifikatoren & physikalische Daten
| CAS No. | 107-43-7 |
|---|---|
| Summenformel | C5H11NO2 |
| Durchschnittliche Molmasse | 117,15 g/mol |
| Monoisotopische Masse | 117,07897859 g/mol |
| SMILES | C[N+](C)(C)CC(=O)[O-] |
| InChIKey | KWIUHFFTVRNATP-UHFFFAOYSA-N |
| PubChem CID | 247 |
| ChEMBL | CHEMBL1182 |
| ChEBI | CHEBI:17750 |
| EC No. | 203-490-6 |
| DTXSID | DTXSID8022666 |
| Lokaler Name | Betain |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 87,6 |
| Stoffklassen | Nitrogen Compounds -> Quaternary Amines |
| Kosmetika | Cosmetic ingredients (Betaine) -> CIR (Cosmetic Ingredient Review)AntistaticViscosity controlling |
| Geschmack | Sweet |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Color/Form | Deliquescent scales or prisms |
| Löslichkeit | SolubleSolubility (g/100 g solvent): methanol, 55ethanol, 8.7. Sparingly soluble in ether.Slightly soluble in chloroformIn water, 6.11X10+5 mg/L at 19 °CVery solubleSoluble (in ethanol)methanol: 0.1 g/mL, clear160 g/100 mL |
| Dietary Ingredients | Betaine |
| Human Drugs | FDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Animal Drugs | Pharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Schmelzpunkt | 301-305°CDecomposes around 293 °C310 °C (dec.) |
| Dampfdruck | 0.00000053 [mmHg]0.05Pa at 25℃ |
| Physical Description | LiquidDry PowderDeliquescent solid[Merck Index] Powder[Alfa Aesar MSDS]Free-flowing, white crystalsSavoury |
| Siedepunkt | 218.95°C (rough estimate) |
| Dichte | 1.00 g/mL at 20 °C |
| Brechungsindex | 1.4206 (estimate) |
| FEMA | 4223 | BETAINE |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Crystals or Crystalline Powder |
| pKa (Säurekonstante) | 1.83(at 0℃) |
| Farbe | colorless |
| Geruch | bland |
| Biologische Quelle | sugar beets |
| Merck | 14,1179 |
| JECFA Number | 2265 |
| BRN | 3537113 |
| Stabilität | Stable. Hygroscopic. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING - HUMECTANTHUMECTANTHAIR CONDITIONING |
| InChI | 1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 |
| InChIKey | KWIUHFFTVRNATP-UHFFFAOYSA-N |
| SMILES | C[N+](C)(C)CC([O-])=O |
| LogP (Verteilungskoeffizient) | -3.1 at 20℃ |
| CAS Datenbank | 107-43-7(CAS DataBase Reference) |
| NIST chemische Informationen | Methanaminium, 1-carboxy-n,n,n-trimethyl-, hydroxide, inner salt(107-43-7) |
| EPA chemische Informationen | Betaine (107-43-7) |
| Absorption | ≤0.05 at 280nm in methanol at 1M≤0.09 at 260nm in methanol at 1M |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 90.4% (274 of 303) of all reports.Not ClassifiedAggregated GHS information provided per 303 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Methanaminium, 1-carboxy-N,N,N-trimethyl-, hydroxide, innersaltRegulation (EC) No 2015/2283 Article 10Methanaminium, 1-carboxy-N,N,N-trimethyl-, inner salt is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanaminium, 1-carboxy-N,N,N-trimethyl-, inner salt are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)REACH registered substance: Betaine (EC: 203-490-6)Trimethylglycine: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | No evidence of mutagenicity[HSDB] Does not cross the placenta well in animal experiments[REPROTOX] Not irritating to skin or eyes of rabbitsNot sensitizing in guinea pig maximization test[IUCLID] May cause irritation[Alfa Aesar MSDS] |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl betaine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Betaine hydrochloride/Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: betaine hydrochloride is included in digestive aid drug products. /Betaine hydrochloride/ |
| EPA Safer Chemical | Chemical: Betaine |
| Hazard Classes and Categories | Not Classified |
| Lagerbedingungen | Store below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by the manufacturer . Protect from moisture . |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Wechselwirkungen | The aim of this study was to assess the pharmacokinetics of orally administered betaine and its acute effect on plasma total homocysteine (tHcy) concentrations. Healthy volunteers (n = 103 men, 7 women) with normal body weight (mean + or - SD, 69.5 + or - 17.0 kg), 40.8 + or - 12.4 yr old, participated in the study. The betaine doses were 1, 3, and 6 g. The doses were mixed with 150 mL of orange juice and ingested after a 12-hr overnight fast by each volunteer according to a randomized double-blind crossover design. Blood samples were drawn for 24 hr and a 24-hr urine collection was performed. Orally administered betaine had an immediate and dose-dependent effect on serum betaine concentration. Single doses of 3 and 6 g lowered plasma tHcy concentrations (P = 0.019 and P < 0.001, respectively), unlike the 1-g dose. After the highest dose, the concentrations remained low during the 24 hr of monitoring. The change in plasma tHcy concentration was linearly associated with betaine dose (P = 0.006) and serum betaine concentration (R2 = 0.17, P = 0.025). The absorption and elimination of betaine were dose dependent. The urinary excretion of betaine seemed to increase with an increasing betaine dose, although a very small proportion of ingested betaine was excreted via urine. In conclusion, a single dose of orally administered betaine had an acute and dose-dependent effect on serum betaine concentration and resulted in lowered plasma tHcy concentrations within 2 hr in healthy subjects.The prophylactic efficiency of taurine or betaine pretreatment for the prevention of peroxidative changes induced by lipopolysaccharide treatment in the rat liver was investigated ... Lipopolysaccharide (10 mg/kg intraperitoneally) was given to rats pretreated with taurine (1.5%, w/v) or betaine (1.5%, w/v) in drinking water for 4 weeks and plasma transaminase activities as well as hepatic malondialdehyde, diene conjugate (DC), glutathione, alpha-tocopherol and ascorbic acid levels, and superoxide dismutase (SOD) and glutathione peroxidase activities were determined ... Significant increases in plasma transaminase activities and hepatic malondialdehyde and DC levels and decreases in hepatic glutathione and alpha-tocopherol levels and SOD and glutathione peroxidase activities were observed 6 h after lipopolysaccharide treatment. This treatment did not alter ascorbic acid levels in the liver compared with controls. Taurine or betaine pretreatment in lipopolysaccharide-injected rats caused significant decreases in plasma transaminase activities and hepatic malondialdehyde and DC levels, and significant increases in glutathione and alpha-tocopherol (not betaine) levels without changing ascorbic acid levels and SOD and glutathione peroxidase activities in the liver ... /According to the authors/ taurine or betaine pretreatment was effective in the prevention of lipopolysaccharide-induced hepatotoxicity and prooxidant status.Concomitant use of betaine and folic acid may be additive with regard to the possible lowering of serum homocysteine levels.... Remethylation of homocysteine to methionine can occur through either the folate-dependent methionine synthase pathway or the betaine-dependent betaine-homocysteine methyltransferase pathway. The relevance of betaine as a determinant of fasting total homocysteine (tHcy) is not known, nor is it known how the 2 remethylation pathways are interrelated ... The objectives of the study were to examine the relation between plasma betaine concentration and fasting plasma tHcy concentrations and to assess the effect of folic acid supplementation on betaine concentrations in healthy subjects ... A double-blind randomized trial of 6 incremental daily doses of folic acid (50-800 ug/day) or placebo was carried out in 308 Dutch men and postmenopausal women (aged 50 to 75 yr). Fasted blood concentrations of tHcy, betaine, choline, dimethylglycine, and folate were measured at baseline and after 12 wk of vitamin supplementation ... Concentrations of tHcy were inversely related to the betaine concentration (r = -0.17, P < 0.01), and the association was independent of age, sex, and serum concentrations of folate, creatinine, and cobalamin. Folic acid supplementation increased betaine concentration in a dose-dependent manner (P for trend = 0.018)the maximum increase (15%) was obtained at daily doses of 400 to 800 ug/day ... /The authors condluded/ the plasma betaine concentration is a significant determinant of fasting tHcy concentrations in healthy humans. Folic acid supplementation increases the betaine concentration, which indicates that the 2 remethylation pathways are interrelated. |
| Hepatotoxicity | In small, open label trials of betaine therapy for homocystinuria as well as in small controlled trials of betaine in other conditions (Alzheimer disease, nonalcoholic steatohepatitis), serum enzyme elevations and clinically apparent liver injury were not reported. Indeed, in some studies, betaine has been associated with significant declines in preexisting serum enzyme elevations in a proportion of patients with nonalcoholic fatty liver disease. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a water solubility of 611,000 mg/L at 19.3 °C(2) and a regression-derived equation(3), indicates that betaine is expected to have very high mobility in soil(SRC). The estimated pKa of betaine, an inner salt, is 2.38(4). Volatilization of betaine from moist soil surfaces is not expected to be an important fate process(SRC) because ionic compounds do not volatilize. Betaine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-8 mm Hg(SRC), determined from a fragment constant method(5). No information on the aerobic biodegradation of betaine was locatedhowever, the mineralization of alkyl betaine surfactants is considerable (>60% BODT reached in 28-day screening tests(6,7)) indicating that it is likely that betaine is also readily mineralized(SRC). Betaine is expected to biodegrade under anaerobic conditions as well based on data indicating that it is removed during anaerobic sewage treatment(8).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a water solubility of 611,000 mg/L at 19.3 °C(2) and a regression-derived equation(3), indicates that betaine is not expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 2.38(4) indicates betaine, will exist entirely as an inner salt at pH values of 5 to 9 and therefore volatilization from water surfaces will not occur as ionic compounds do not volatilize. According to a classification scheme(5), an estimated BCF of 0.3(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). No information on the aerobic biodegradation of betaine was locatedhowever, the mineralization of alkyl betaine surfactants is considerable (>60% BODT reached in 28-day screening tests(7,8)) indicating that it is likely that betaine is also readily mineralized(SRC). Betaine is expected to biodegrade under anaerobic conditions as well based on data indicating that it is removed during anaerobic sewage treatment(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), betaine, which has an estimated vapor pressure of 1.4X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase betaine may be removed from the air by wet or dry deposition(SRC). Betaine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(3). |
| Lebensmitteluntersuchungswerte | The betaine concentration of over 400 foods in the U.S. was measured. Concentrations ranged from 0.3 to 1.9 mg/100 g food for 26 dairy and egg products, 0.4 to 28.8 mg/100 g food for 16 spices, 0 to 1.8 mg/100 g food for 7 samples of fats and oils, 1.8 to 23.3 mg/100 g food for 16 samples of chicken and turkey, 2.1 to 10.4 mg/100 g for 18 sausage and luncheon meats, 0.5 to 1396.1 mg/100 g for 15 samples of breakfast cereals, 0.1 to 0.8 mg/100 g for 35 fruits, 0.2 to 4.2 mg/100 g food for 10 pork product samples, 0.1 to 808.6 mg/100 g food for 62 vegetable products with beets and spinach containing significantly more betaine than other vegetables, 0.3 to 11.2 mg/100 g food for 12 nut and seed products, 6.3 to 12.8 mg/100 g food for 15 beef products, 0.1 to 8.1 mg/100 g food for 12 beverages, 2.1 to 62.1 mg/100 g food for 11 finfish and shellfish products, 0.1 to 39.6 mg/100 g food for 21 legumes and legume products, 7.6 to 33.9 mg/100 g food for 4 lamb, veal and game samples, 0.4 to 244.1 mg/100 g food for 43 baked products, 0.1 to 6.1 mg/100 g food for 20 sugars and sweets products, 0.3 to 1506.8 for 13 samples of cereal grains and pasta products, 0.5 to 98.2 mg/100 g for 50 samples of fast foods, 0.1 to 21.6 mg/100 g for 10 snacks (pretzels were 295.1 mg/100 g food)(1). |
| Milk Concentrations | ENVIRONMENTAL: Concentrations of betaine in 5 samples of milk ranged from 0.6 to 1.9 mg/100 g milk(1). |
| Toxizitätsübersicht | The CIR Expert Panel concluded that the eleven alkyl betaines listed below are safe in the present practices of use and concentration in cosmetics, when formulated to be non-irritating...Betaine...Safe for use in cosmetics, with qualifications |
| Effluent Concentrations | Betaine was detected in the effluent of processes using sugar-beet molasses as a substrate at concentrations up to 4.5 g/dm-3(1). |
| Soil Adsorption/Mobility | The Koc of betaine is estimated as 3(SRC), using a water solubility of 611,000 mg/L at 19.3 °C(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that betaine is expected to have very high mobility in soil. The estimated pKa of betaine, an inner salt, is 2.38(4). |
| Natural Pollution Sources | Betaine is widely distributed in both plants and animals(1) as a nonproteinogenic amino acid(2). |
| Artificial Pollution Sources | Betaine's production and use in soldering, resin curing fluxes, organic synthesis and in the treatment of homocystinuria(1) and as a lipotrophic drug(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: No data on the aerobic biodegradation of betaine was located however, amphoteric surfactants based on the betaine structure have been shown to be mineralized to a significant extent. For example, C12-C14 alkyl betaine surfactants were shown to be readily biodegradable in 28-day closed bottle screening tests reaching >60% of the theoretical oxygen demand over this period(1,2).ANAEROBIC: Betaine was nearly completely degraded in two full-scale anaerobic treatment plants(1). |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)BetainevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| F | 3-10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29239000 |
| RTECS-Nr. | DS5900000 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 107-43-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Betaine is a natural compound extracted from Beta vulgaris, widely present in both leaves and roots. Within plants, betaine is synthesised through a two-step oxidation of choline within chloroplasts. The first step converts choline into betaine aldehyde, a rate-limiting step catalysed by choline monooxygenase. The second step converts betaine aldehyde to betaine, catalysed by betaine aldehyde dehydrogenase [1]. It possesses certain pharmacological activities and may be employed to treat deficiencies or defects in specific enzymes leading to hyperhomocysteinemia in blood and urine. This medication facilitates the removal of excess homocysteine from the body.[1] TAKABE T, TANAKA Y, TAKABE T. CHAPTER 2:Betaine in Sugar Beet[C]. 2015: 0. DOI:10.1039/9781782628446-00009.
Verwenden
betaine is a surfactant, humectant, and excellent skin conditioner. It is also used to build product viscosity and as a foam booster. It is found mostly in skin cleansers, shampoos, and bath products.