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Beta-Alanine

HCID 239
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Basic information

CAS
107-95-9
Standard SMILES
NCCC(=O)O
InChIKey
UCMIRNVEIXFBKS-UHFFFAOYSA-N
Molecular formula
C3H7NO2
Average molar mass
89.09 g/mol
Monoisotopic mass
89.04767847

Overview

Beta-alanine is a naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position. It has a role as a neurotransmitter, an inhibitor, an agonist, a human metabolite and a fundamental metabolite. It is a conjugate acid of a beta-alaninate. It is a tautomer of a beta-alanine zwitterion.

Names & identifiers

Preferred name
Beta-Alanine
IUPAC
3-aminopropanoic acid
English name
β-Alanine
Molecular formula
C3H7NO2
Molecular weight
89.09

Names & synonyms

beta-alanine107-95-93-Aminopropanoic acid3-Aminopropionic acidAbufeneBeta Alaninebeta-Aminopropionic acid2-Carboxyethylamineomega-Aminopropionic acid3-AminopropanoateFEMA No. 325211P2JDE17B
Show more names
β-AlaB-ALANINEH-β-Ala-OHBETA-ALAAnalineBeta alanine powderFEMA 3252
I2-AlanineNSC-7603beta Alanine HydrochlorideDTXSID0030823CHEBI:169583 Aminopropionic AcidRefChem:567109Hydrochloride, beta-Alanine

Database identifiers

CAS
107-95-9、28854-76-4
PubChem CID
239
DTXSID
DTXSID0030823
ChEMBL
CHEMBL297569
ChEBI
CHEBI:16958
UNII
11P2JDE17B
EC Number
203-536-5
Nikkaji
J4.070C

Properties

Computed structural properties

XLogP
-3
Topological polar surface area
63.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
6
Formal charge
0
Complexity
52.8

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Biochemical Research
Drugs · 2 items

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

LogP-3.05
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 3 items

545.0 mg/mL

Soluble in water; Insoluble in ether and acetone

Slightly soluble (in ethanol)

Dietary IngredientsBeta-alanine
Melting Point200 °C
Vapor Pressure0.00000005 [mmHg]
Physical Description · 3 items

Solid; [Merck Index] White crystalline solid; [Alfa Aesar MSDS]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 98.5% (322 of 327) of all reports.

Not Classified

Aggregated GHS information provided per 327 reports by companies from 5 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 4 items

Chemical: .beta.-Alanine

Regulation (EC) No 1831/2003 (amended)

REACH registered substance: β-alanine (EC: 203-536-5)

.beta.-Alanine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] May cause eye irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesNot Classified

Toxicology

Health EffectsChronically high levels of beta-alanine are associated with at least 2 inborn errors of metabolism including: GABA-Transaminase Deficiency and Methylmalonate Semialdehyde Dehydrogenase Deficiency.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

Chemistry & industry

Pharmacology

Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysAspartate Metabolism

Uses & manufacturing

Uses · 4 items

Used to make pantothenic acid and derivatives and as a buffer in electroplating; [Merck Index] Used as flavoring agent or adjuvant and nutritional supplement; [FDA] An amino acid not found in protein; Used in organic synthesis and biochemical research; [Alfa Aesar MSDS]

Electroplating [Category: Plate]

Use (kg; approx.) in Germany (2009): >1000

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Use Classification · 3 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information.beta.-Alanine: ACTIVE
Applications · 8 items

DescriptionBeta-alanine is a non-proteogenic amino acid that is produced endogenously in the liver. In addition, humans acquire beta-alanine through the consumption of foods such as poultry and meat. By itself, the ergogenic properties of beta-alanine are limited; however, beta-alanine has been identified as the rate-limiting precursor to carnosine synthesis, and has been consistently shown to increase levels of carnosine in human skeletal muscle. Doses of 4 to 6 g/day of beta-alanine have been shown to increase muscle carnosine concentrations by up to 64 % after 4 weeks, and up to 80 % after 10 weeks. Baguet et al. demonstrated that individuals vary in the magnitude of response to 5 to 6 weeks of betaalanine supplementation (4.8 g/day), with high responders increasing muscle carnosine concentrations by an average of 55 %, and low responders increasing by an average of only 15 %. The difference between high and low responders seems, at least in part, to be related to baseline muscle carnosine content and muscle fiber composition. β-Alanine, a β−amino acid, is a component of pantothenic acid and the rate-limiting amino acid in the biosynthesis of the histidinyl antioxidant dipeptides carnosine and anserine. Endogenous β-amino acid that is a nonselective agonist at glycine receptors and a ligand for the G protein-coupled orphan receptor, TGR7 (MrgD). β-Alanine flux plays a cytoprotective role by supporting the osmotic stability of marine organisms, preimplantation mouse embryos and mammalian cells exposed to hypoxic stress.

Related reactions

553 records
New reaction record
HRID 5684 reaction equation
HRID 5684As reactantuspto-grants-1993_09
HRID 5690 reaction equation
HRID 5690As reactantuspto-grants-1993_09
HRID 5896 reaction equation
HRID 5896As reactantuspto-grants-1993_09
HRID 6438 reaction equation
HRID 6438As reactantuspto-grants-1993_09
HRID 12008 reaction equation
HRID 12008As reactantuspto-grants-2010_06
HRID 27128 reaction equation
HRID 27128As reactantuspto-grants-1980_09
HRID 54161 reaction equation
HRID 54161As reactantuspto-grants-1997_04
HRID 71632 reaction equation
HRID 71632As reactantuspto-grants-2014_09
Page 1 of 70

Compound notes

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Solid

Colourless needles;

Ionization Efficiency · 6 items

Positive

2.15

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Dissociation Constants · 2 items

10.2

3.63 (at 5 °C)

Physicochemical properties

Melting point
202 °C · 202 °C (dec.)(lit.)
Boiling point
237.1 · 237.1±23.0 °C(Predicted)
bulk density
770 kg/m3 · 770kg/m3
Density
1 · 1,437 g/cm3
FLAVIS Number
17.001 · 17.001 | beta-Alanine
refractive index
1.465 · 1.4650 (estimate)
FEMA
3252 · 3252 | BETA-ALANINE
Flash point
204 · 204-206°C
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
2 O: · H2O: 1 M at 20 °C, clear, colorless
pka
3.55 · 3.55(at 25℃)
form
Crystalline Powder
color
White
PH
6 · 6.0-7.5
Odor
100 % · at 100.00 %. odorless
Odor Type
odorless
biological source
synthetic
Water Solubility
Soluble in water(550g/L). Slightly soluble in alcohol. Insoluble in ether and acetone.
Decomposition
204 · 204-206 ºC
λmax
260 nm · λ: 260 nm Amax: ≤0.02λ: 280 nm Amax: ≤0.02
Merck
14 · 14,205
JECFA Number
1418 · 1418
BRN
906793 · 906793
Stability
Stable. Keep dry.
Cosmetics Ingredients Functions
HUMECTANT
InChI
1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
InChIKey
UCMIRNVEIXFBKS-UHFFFAOYSA-N
SMILES
NCCC(O)=O || NCCC(O)=O
LogP
-0.882 · -0.882 (est)
Substances Added to Food (formerly EAFUS)
BETA-ALANINE
CAS DataBase Reference
107 · 107-95-9(CAS DataBase Reference)
FDA UNII
11 P2JDE17B · 11P2JDE17B
NIST Chemistry Reference
Beta-alanine(107-95-9)
EPA Substance Registry System
.beta.-Alanine (107-95-9)
UNSPSC Code
85151701 · 85151701
NACRES
75 · NA.75
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
24 · 24/25-36-26
WGK Germany
3 · 3
RTECS
2369200 · UA2369200
TSCA
TSCA listed
HS Code
2922499990 · 2922499990
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Active
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
UA2369200
hs_code
2922499990
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
24/25-36-26
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P305+P351+P338

UsesIt is widely used in medicine, feed, food, and other industries, mostly to synthesize pantothenic acid and calcium pantothenate (a medicine and feed additive), carnosine, pamidronate sodium, barley nitrogen. It is also used to produce plating corrosion inhibiter, as a biological reagent, and as an organic synthesis intermediate. Used as a food and health supplement additive. Endogenous beta-amino acids, non-selective glycine receptor agonists ,G-protein-coupled orphan receptor (TGR7, MrgD) ligand. Relying on the stability of marine biology, beta-aminopropionic acid has a protective effect on cells.

Descriptionβ-Alanine (or beta-alanine) is a naturally occurring beta amino acid, which is an amino acid in which the amino group is at the β- position from the carboxylate group (i.e., two atoms away. The IUPAC name for β-alanine is 3-amino propanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter. β-Alanine is not used in the biosynthesis of any major proteins or enzymes. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (vitamin B5), which itself is a component of coenzyme A. Under normal conditions, β-alanine is metabolized into acetic acid. β-Alanine is the rate-limiting precursor of carnosine, which is to say carnosine levels are limited by the amount of available β-alanine. Supplementation with β-alanine has been shown to increase the concentration of carnosine in muscles, decrease fatigue in athletes and increase total muscular work done.Typically, studies have used supplementing strategies of multiple doses of 400 mg or 800 mg, administered at regular intervals for up to eight hours, over periods ranging from 4 to 10 weeks . After a 10 - week supplementing strategy, the reported increase in intramuscular carnosine content was an average of 80.1% (range 18 to 205%).

OccurrenceReported to occur as a component in amino acids; carnosine, anserine, pantothenic acid

UsesEffective catalyst for the Knoevenagel condensation. Beta Alanine is used as nutrition supplements in food production. Increase muscular strength & power output, Increases Muscle Mass, increase Anaerobic Endurance.

Usesβ-Alanine is a naturally occurring beta amino acid. β-Alanine is formed in vivo by the degradation of dihydrouracil (D449990) and carnosine. β-Alanine is also the rate-limiting precursor of carnosine, as a result supplementation with β-alanine increases the concentration of carnosine in muscles.

Usesβ-Alanine has been used as a ligand for the orphan MAS-related receptor. It has also been used in culture media used for certain strains of yeast to test for β-alanine auxotrophy.

General DescriptionAn N-blocked form of alanine.

Preparation methods · 2 items

PreparationAcrylonitrile and ammonia react in a solution of diphenylamine and t-butanol to create beta-aminopropionitrile, which is then alkalized to obtain beta-aminopropionic acid. In a dry autoclave, sequentially add acrylonitrile, diphenylamine and t- butanol, and stir for 5min. Then, add liquid ammonia, maintain the temperature at 100-109℃ and pressure at 1MPa, and stir for 4h. Cool to below 10℃ and stop mixing when the pressure reaches atmospheric pressure. At 65-70℃/(8.0-14.7kPa), decrease the pressure to recover t-butanol to obtain crude beta-aminopropionitrile. Distill the crude product under low pressure, collect the 66-105℃/(1.33-4.0kPa) distillation to obtain beta-aminopropionitrile, and maintain temperature for 1h. Steam under low pressure for half an hour to remove the ammonia in the reaction solution, add water, and drop in hydrochloric until PH reaches 7-7.2. Filter to remove trace impurities. Concentrate the filtered liquid until a large amount of solid precipitates, extract while hot and cool to below 10℃. Filter and vacuum dry to obtain beta-aminopropionic acid. This method requires 982kg beta-aminopropionitrile for every ton of product, and the yield of alkalization is 90%. Place the alkaline sodium hypochlorite solution obtained from degradation of succinimide (Hoc reaction) (containing 14% sodium hypochlorite, 8% sodium hydroxide, 30% sodium carbonate) and ice into a reaction chamber, mix and add succinimide, and let react at 18-25℃ for 0.5h. Increase temperature to 40-50℃ and allow to react for 1h. Add hydrochloric acid to adjust the PH to 4-5, decrease the pressure to condense. After condensed and cooled, add 3 times the amount of 95% ethanol to allow inorganic salts to precipitate, filter, and repeat once again. Then, dilute the filtered liquid with 4 times the amount of distilled water and reflux for 1h. Add activated charcoal to remove color, filter, and pass the filtered liquid through exchange resin. Add activated charcoal to remove color, filter, decrease pressure to condense, cool to crystalize, filter, use distilled water to recrystallize once, and obtain beta-aminopropionic acid. Hydrolyze and acidify beta-aminopropionitrile to obtain.

PreparationBy heating acrylic acid with concentrated aqueous ammonia under pressure, by addition of acrylonitrile to phthalimide or to ammonia; from β-aminopropionitrile, from succinimide by the Hofmann degradation.

Upstream & downstream products

Upstream raw materials

Sodium hypochlorite3-AminopropionitrileSuccinimideAMBERLITE(R) IRA-400 (CL)DiphenylamineActivated carbon,decolor

Downstream products

N-t-Boc-β-alaninecalcium di-beta-alaninate3-Maleimidopropionic acidPantothenic acid calcium salt monohydrateH-beta-Ala-OtBu HClEthyl 3-(isopropylamino)propanoateBENFURACARBCalcium D-Pantothenate2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamideL-AlaninePENTAGASTRIN5-Chloro-1H-indazole-3-carboxylic acidDisperse Blue 148Pamidronic acidN-hydroxyethyl-N-hydroxyalkyl-β-alanineN-(tert-Butoxycarbonyl)-4-piperidoneethyl 3-(chlorosulfanyl-propan-2-yl-amino)propanoateD-Pantothenic acid3-aminopropanal

Additional notes

DefinitionChEBI: A naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position.