L-Alanine
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L-Alanine
structure -
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CAS No:
56-41-7
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Formula:
C3H7NO2
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Chemical Name:
L-Alanine
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Synonyms:
L-Alanine;Alanine,L-;L-α-Alanine;L-2-Aminopropanoic acid;L-α-Aminopropionic acid;α-Alanine;(S)-Alanine;L-(+)-Alanine;Alanine;Propanoic acid,2-amino-,(S)-;L-2-Aminopropionic acid;α-Aminopropionic acid;(S)-2-Aminopropanoic acid;(S)-(+)-Alanine;NSC 206315;(2S)-2-Aminopropanoic acid;Lactamine;2-Aminopropionic acid;(2S)-2-Aminopropanoic acid;(2S)-2-Azaniumylpropanoate;8: PN: WO2021055880 SEQID: 9 claimed protein;115967-49-2;6898-94-8;759445-89-1;787635-21-6;170805-71-7;1150316-17-8
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CAS No:
Description
A white, odorless powder having a sweet taste White crystalline powder
OtherSolid|Solid
L-alanine is the L-enantiomer of alanine. It has a role as an EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor and a fundamental metabolite. It is a pyruvate family amino acid, a proteinogenic amino acid, a L-alpha-amino acid and an alanine. It is a conjugate base of a L-alaninium. It is a conjugate acid of a L-alaninate. It is an enantiomer of a D-alanine. It is a tautomer of a L-alanine zwitterion.|Alanine is a non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and the central nervous system.|A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.
L-Alanine Basic Attributes
89.09
89.09
1720248
200-273-8
DTXSID20107828
Orthorhombic crystals from water|White crystalline powder
29224995
Characteristics
63.3
-3
White to almost white powder
1.432 g/cm3 @ Temp: 22 °C
300 °C (decomp)
250 deg C (sublimes)
82.6ºC
H2O: 166.5 g/L (25 ºC)
Store at RT.
1.05X10-7 mm Hg at 25 deg C (est)
14.5 º (c=10,6N HCl,dry sub.)
Odorless
Sweet taste
2.34(at 25 °C)
Henry's Law constant = 1.5X10-9 atm-cu m/mol at 25 °C (est)
2.34 (at 25 °C)|pKa1 = 2.34 /carboxylic acid/; pKa2 = 9.69 /primary amine/
PRISMS; DECOMP @ 204 °C /L-ALANINE HYDROCHLORIDE/|UV: 2-10 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /Alpha-alanine (dl)/|Hydroxyl radical reaction rate constant = 3.5X10-11 cu cm/molecule-sec at 25 °C (est)
Safety Information
IRRITANT
3
36/37/38
24/25-36-26
AY2990000
Xi
Stable. Incompatible with strong oxidizing agents.
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
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.
L-Alanine is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
Not Classified
Toxicity
L-Alanine, a nonessential amino acid, is produced within living organisms(1). Dietary intake of L-alanine is not essential for life since sufficient quantities are produced within the human body(1).
L-Alanine's production and use in microbiological and biochemical research and as a dietary supplement(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 31.7-65(2), indicate that L-alanine is expected to have very high to high mobility in soil(SRC). Measured pKa values of 2.34 (carboxylic acid) and 9.69 (primary amine)(3), indicate that this compound will exist as a zwitterion in the environment. Volatilization of L-alanine from moist soil surfaces is not expected to be an important fate process(SRC) since ionic compounds do not volatilize. L-Alanine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). L-Alanine is expected to biodegrade in soil based on 61-81% loss of C-14 labeled carbon as CO2 from loam and sandy loam soil after 1 week(5).|AQUATIC FATE: Based on a classification scheme(1), measured Koc values ranging from 31.7-65(2), indicate that L-alanine is not expected to adsorb to suspended solids and sediment(SRC). Measured pKa values of 2.34 (carboxylic acid) and 9.69 (primary amine)(3), indicate that this compound will exist as a zwitterion in the environment. Volatilization of L-alanine from water surfaces is not expected to be an important fate process(SRC) since ionic compounds do not volatilize. According to a classification scheme(4), a BCF of 0.004(SRC), from its log Kow of -2.85(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). L-Alanine is expected to biodegrade in water based on 96% degradation after 23 days measured in a screening test using an activated sludge inoculum(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), L-alanine, which has an estimated vapor pressure of 1.1X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase L-alanine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 11 hours(SRC), calculated from its rate constant of 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase L-alanine may be removed from the air by wet or dry deposition(SRC). L-Alanine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).
The rate constant for the vapor-phase reaction of L-alanine with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). L-Alanine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). L-Alanine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(2).
An estimated BCF of 0.004 in fish was calculated for L-alanine(SRC), using an estimated log Kow of -2.85(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Koc values of 35.7 and 31.7-65 have been measured for alanine in surface sediment(1). According to a classification scheme(2), these Koc values suggest that L-alanine is expected to have very high to high mobility in soil. Measured pKa values of 2.34 (carboxylic acid) and 9.69 (primary amine)(3), indicate that this compound will exist as a zwitterion in the environment.
Measured pKa values of 2.34 (carboxylic acid) and 9.69 (primary amine)(1), indicate that this compound will exist as a zwitterion in the environment. Volatilization of L-alanine from moist soil or water surfaces is not expected to be an important fate process(SRC) since ionic compounds do not volatilize. L-Alanine is not expected to volatilize from dry soil surfaces(SRC) based upon a an estimated vapor pressure of 1.1X10-7 mm Hg(SRC), determined from a fragment constant method(2).
SURFACE WATER: The concentrations of alanine measured at different locations in the estuary of the Tama River in Japan ranged from 0.73-1.50 umol/L(1).|RAIN/SNOW/FOG: Alanine was detected in 40 out of 73 rain samples collected in the rural, continental town of Charlottesville, VA(1). The mean, median, and range of alanine concentrations were 59, 18, and 2-960 nM, respectively(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 18,364 workers (14,698 of these are female) are potentially exposed to L-alanine in the US(1). Occupational exposure to L-alanine may occur through dermal contact with this compound at workplaces where L-alanine is produced or used(SRC). Monitoring data indicate that the general population may be exposed to L-alanine via ingestion of food, ingestion of this substance as a dietary supplement, and dermal contact with this compound and other consumer products containing L-alanine(SRC).
Drug Information
Used for protein synthesis.|Treatment of Multiple Myeloma|Parenteral nutrition|Supplementation of amino-acids where parenteral nutrition is required.
Exptl Ther: ... Therapy of acute water diarrhea is reported in 94 male patients, aged 6-59 yr, of whom 49 were given a standard dextrose (glucose) based formula, to a total dose of 105-1719 ml/kg, and 45 were given the same soln with added alanine 90 uM/l, to a total dose of 60-1035 ml/kg. All patients were also given iv injections of replacement soln and oral tetracycline. The median stool output/kg body weight during the initial 24 hr of treatment until diarrhea stopped was reduced in those given the soln containing alanine as compared to controls. Intake of oral rehydration soln was reduced in those given alanine. Two patients given alanine soln and 18 given the standard treatment required unscheduled rapid iv replacement soln to correct signs of dehydration during oral therapy.|DIETARY SUPPLEMENT|Used in pharmaceutical preparations for injection or infusion; dietary supplement and flavor compounds in maillard reaction products; stimulant of glucagon secretion
Is an important source of energy for muscle tissue, the brain and central nervous system; strengthens the immune system by producing antibodies; helps in the metabolism of sugars and organic acids.
L-Alanine is a non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and the central nervous system. BCAAs are used as a source of energy for muscle cells. During prolonged exercise, BCAAs are released from skeletal muscles and their carbon backbones are used as fuel, while their nitrogen portion is used to form another amino acid, Alanine. Alanine is then converted to Glucose by the liver. This form of energy production is called the Alanine-Glucose cycle, and it plays a major role in maintaining the body's blood sugar balance.
/ALTERNATIVE and IN VITRO TESTS/ The amino acid L-alanine has been shown to exert long-term cytoprotection by as yet unidentified molecular mechanisms. Using cultured human endothelial cells (ECV 304), the present study investigates the effect of L-alanine on hydrogen peroxide-mediated cytotoxicity and expression of the antioxidant stress proteins, heme oxygenase-1 (HO-1) and ferritin. Pretreatment with L-alanine (0.3-3mM) protected endothelial cells from hydrogen peroxide-dependent cytotoxicity and increased the surviving endothelial cell fraction by 76%. The described protection was associated with a significant induction of heme oxygenase activity and ferritin protein synthesis. A protective effect similar to L-alanine was observed when preincubating the cells with iron-free apoferritin or the antioxidant HO-1 product, bilirubin. The present study demonstrates that L-alanine stimulates expression of the antioxidant defense proteins HO-1 and ferritin in endothelial cells. Increased heme oxygenase activity and ferritin expression improve endothelial dysfunction suggesting an antiatherogenic potential of L-alanine.|/OTHER TOXICITY INFORMATION/ The response to a primed constant infusion of alanine 2 mg/kg/min on glucose and urea kinetics in 4 healthy overnight fasted subjects was /studied/ by use of concurrent primed infusions of 6,6-d2-glucose and radiolabeled urea. When no alanine was infused, plateaus in glucose and urea concn and enrichment were maintained for the final 3 hr of 4 hr infusion of tracers. When alanine was infused over the final 2 hr of a second protocol, urea enrichment decr significantly, indicating an incr in urea production corresponding to a potential incr in glucogenesis from alanine of 20%. The alanine infusion had no effect on either the plasma concn or enrichment of glucose, suggesting hepatic glucose output was not affected.
Abufène
L-Alanine Use and Manufacturing
Method 1. Enzymatic method applies enzyme engineering technology, takes L-aspartic acid as raw material, and produces L-alanine under the action of β-deacidase of Pseudomonas de Aquinha. Process: L-aspartic acid Acid [immobilized aspartate β-decarboxylase (decarboxylation)]→[37℃, pH6.0] decarboxylation [concentration, crystallization]→[pressure reduction, 5℃] crystallization [refined]→[5℃] L- Cultivation of crude alanine strains of Pseudomenas daconhae (Pseudomenas daconhae) 68 different strains, using slant medium, composed of peptone 0.25%, beef extract 0.52%, yeast extract 0.25%, NaCl 0.5% , pH7.0, 2.0% agar. The seed medium is the same as the slant medium, but without the addition of agar, the medium volume in a 250mL Erlenmeyer flask is 40mL. The composition of the shake flask medium is 3.0% guine acid, 0.9% peptone, 0.5% casein hydrolysate, and phosphoric acid Potassium dihydrogen 0.05%, MgSO4.7H2O 0.01%, adjust the pH to 7.2 with ammonia water, the medium volume in the 500ml Erlenmeyer flask is 80ml, inoculate the fresh slant strains cultured for 24h in the seed medium, shake culture at 30℃ 8h, then inoculate it in a shake flask culture medium, shake culture at 30°C for 24h, and then gradually expand to culture in a culture tank of 1000-2000ml. After the cultivation, the pH was adjusted to 4.75 with 1mol/L HCl, and the temperature was incubated at 30°C for 1 hour. Centrifuge with a rotating drum centrifuge to collect the bacterial cells (containing L-aspartate-β-decarboxylase). Cell fixation Take 20kg of the above wet bacteria, add physiological saline and stir evenly and dilute to 40L. Take another 85L of 50g/L (5%) carrageenan solution dissolved in physiological saline, keep the two liquids at 45℃ and mix, cool to 5℃ to form a gel, immerse it in 600L containing 20g/L (2%) KCl and 0.2mol/L hexamethylenediamine 0.5mol/L, pH7.0 phosphate buffer, stir for 10min at 5℃, add glutaraldehyde to 0.6 mol/L, stir at 5℃ for 30min, remove and cut into 3-5mm3 After the block is fully washed with 20 g/L KCl solution, it is obtained by filtering off the washing liquid and set aside. Preparation of bioreactor The immobilized Pseudomonas is loaded into a packed bed reactor (30 cm×180 cm) with a pressure of 1.515×107 Pa, and it is ready for use. For decarboxylation, take the 37℃ L-aspartic acid solution (1mol/L), add pyridoxal phosphate to a concentration of 0.1 mmol/L, adjust the pH 6.0, adjust the pH 6.0, keep 37℃, and flow into a fixed space at a certain space Pseudomonas bioreactor for decarboxylation to control the maximum conversion rate (>95%), and collect the decarboxylation solution to obtain crude L-alanine solution. Refine the clear decarboxylation solution, concentrate it under reduced pressure at 60-70°C to half of its original volume, add an equal volume of methanol after cooling, crystallize at 5°C, let stand overnight, filter the crystals, wash with a small amount of cold methanol, drain, and 80°C Dry in vacuum to obtain crude L-alanine. Then add the crude product to 3 times volume of deionized water, stir to dissolve at 80℃, add 5 g/L (0.5%) activated carbon, stir for 1h at 70℃, filter to take the filtrate, cool, add equal volume of methanol, crystallize at 5℃, filter After taking the crystals and vacuum drying at 80°C, the fine L-alanine is obtained. Method 2. The immobilized enzyme uses fumaric acid as a raw material, first converts it with NH3 into L-aspartic acid under the action of aspartic acid, and then fixes the β-aspartic acid of Pseudomonas de Acunha in the same way as the above enzymatic method. -Decarboxylase under the action of decarboxylase to obtain L-alanine. Process: Fumaric acid [immobilized aspartase (conversion)]→[37℃, pH8.5] conversion solution [immobilized aspartate-β-decarboxylase]→[37℃, pH6.0] decarboxylation Liquid [concentration, crystallization]→[decompression, 5℃] crystallization [refining]→[5℃] L-alanine aspartase immobilized cell seed cultivation, immobilization, preparation of bioreactors. See the aspartase conversion process for details. For decarboxylation of immobilized aspartate-β-decarboxylase, refer to the above-mentioned enzymatic process for purification. Method three, chemical synthesis method Strecker method Bucherer method and then optical resolution to obtain L-alanine fine product.
This product is used to make vitamin B6, synthetic calcium pantothenate and other organic compounds. Adding to food can enhance the flavoring effect of chemical seasonings, improve the taste of sweeteners and the sour taste of organic acids, improve the quality of alcoholic beverages, prevent the oxidation of oils and improve the flavor of impregnated foods. It can also be used as a biochemical reagent for biochemical and microbiological research.
Intermediates
World market for L-alanine in 1982: 130 tonnes; World market for DL-alanine in 1982: 2000 tonnes, in 1984: 700 tonnes|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3590]
GRADES: REAGENT; TECHNICAL.|Reagent grade; USP and FCC grades
All other chemical product and preparation manufacturing|L-Alanine: ACTIVE|Alanine is used for meat and poultry Maillard flavors. It is used to a lesser extent for chocolate, cocoa, cream, butter, and tobacco Maillard flavors.|AN AMINO ACID CLASSIFIED AS NON-ESSENTIAL FOR THE MAINTENANCE OF GROWTH IN RATS.
MICROBIOLOGICAL ASSAY METHODS.|AMINO ACID ANALYZER & GLC DETERMINATION.|AOAC method 960.47, Amino Acids in Vitamin Preparations; microbiological method using basal media. /Amino acids/|The following methods have been developed for the analysis of free amino acids in blood, food, and feedstocks: (1) Protein hydrolysis, (2) Chromatographic methods that include high performance liquid chromatography (HPLC), gas chromatography (GC) and thin-layer chromatography (TLC), (3) Colorimetric and Fluorimetric Analysis, (4) Spectrometric Analysis, and (5) Enzymatic Determination and Microbial Assay. /Amino acids/|For more Analytic Laboratory Methods (Complete) data for (L)-ALANINE (15 total), please visit the HSDB record page.
L-ALANINE DETERMINATION /IN LIVER TISSUE EXTRACTS/ WITH ALANINE DEHYDROGENASE & UV SPECTROPHOTOMETRY.
Food additives -> Flavoring Agents|Human Drugs -> EU pediatric investigation plans|Cosmetics -> Antistatic
Flavoring Agents
Computed Properties
Molecular Weight:89.09
XLogP3:-3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:89.047678466
Monoisotopic Mass:89.047678466
Topological Polar Surface Area:63.3
Heavy Atom Count:6
Complexity:61.8
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Promotes normal protein metabolism in the human body, corrects negative nitrogen balance, supplements protein, and accelerates wound healing; essential for amino acid metabolism in trauma patients (high content of alanine and proline)
Registered Holders
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AJINOMOTO HEALTH AND NUTRITION NORTH AMERICA INC
Active
United States
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AMINO GmbH
Active
Germany
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SHIJIAZHUANG JIRONG PHARMACEUTICAL CO LTD
Active
United States
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L-ALANINE (D7) Formula
74280-71-0
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L-Alanine homopolymer Formula
25191-17-7
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L-Alanine 1,1-dimethylethyl ester Formula
21691-50-9
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L-Alanine isopropyl ester hydrochloride Structure
39825-33-7
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L-Alanine isopropyl ester hydrochloride Structure
62062-65-1
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What is L-Alanine methyl ester
10065-72-2
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What is L-Lysine, polymer with L-alanine
26701-37-1