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β-Alanin

Beta-Alanine

HCID 239
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Grundinformationen

CAS
107-95-9
Standard-SMILES
NCCC(=O)O
InChIKey
UCMIRNVEIXFBKS-UHFFFAOYSA-N
Summenformel
C3H7NO2
Durchschnittliche Molmasse
89,09 g/mol
Monoisotopische Masse
89,04767847

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Beta-Alanine
IUPAC
3-aminopropanoic acid
Lokaler Name
β-Alanin
Englischer Name
β-Alanine
Summenformel
C3H7NO2
Molmasse
89.09

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-3
Polarare Oberfläche (TPSA)
63,3 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
2
Schwere Atome
6
Formalladung
0
Komplexität
52,8

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Uses -> Biochemical Research
Drugs · 2 Einträge

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 Einträge

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 Einträge

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

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 3 Einträge

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.

Gefahrenhinweise

Regulatory Information · 4 Einträge

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

Toxikologische Informationen

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).

Sicherheitsdaten

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysAspartate Metabolism

Verwendung und Herstellung

Uses · 4 Einträge

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 Einträge

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
Anwendungen · 3 Einträge

Beschreibungβ-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%).

Zugehörige Reaktionen

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Solid

Colourless needles;

Ionization Efficiency · 6 Einträge

Positive

2.15

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Dissociation Constants · 2 Einträge

10.2

3.63 (at 5 °C)

Physikochemische Eigenschaften

Schmelzpunkt
202 °C · 202 °C (dec.)(lit.)
Siedepunkt
237.1 · 237.1±23.0 °C(Predicted)
Dichte
1 · 1,437 g/cm3
Brechungsindex
1.465 · 1.4650 (estimate)
FEMA
3252 · 3252 | BETA-ALANINE
Flammpunkt
204 · 204-206°C
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
2 O: · H2O: 1 M at 20 °C, clear, colorless
pka
3.55 · 3.55(at 25℃)
Aggregatzustand
Crystalline Powder
Farbe
White
PH
6 · 6.0-7.5
Geruch (Odor)
100 % · at 100.00 %. odorless
Geruchsart
odorless
Biologische Quelle
synthetic
Wasserlöslichkeit
Soluble in water(550g/L). Slightly soluble in alcohol. Insoluble in ether and acetone.
Decomposition
204 · 204-206 ºC
Merck
14 · 14,205
JECFA Number
1418 · 1418
BRN
906793 · 906793
Stabilität
Stable. Keep dry.
Kosmetik-Inhaltsstoffe Funktionen
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)
CAS Datenbank
107 · 107-95-9(CAS DataBase Reference)
NIST chemische Informationen
Beta-alanine(107-95-9)
EPA chemische Informationen
.beta.-Alanine (107-95-9)
wgk
3
tsca
TSCA listed
hs_code
29224920
RTECS-Nr.
UA2369200
risk_code
36/37/38
hazard_code
Xi
safety_code
24/25-36-26
Speicherklasse
11 - Combustible Solids

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

Verwendenβ-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.

Darstellung

synthetischeBy 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Natriumhypochlorit3-AminopropiononitrilSuccinimidAMBERLITE(R) IRA-400 (CL)DiphenylaminActivated carbon,decolor

Nachgelagerte Produkte

N-t-Boc-β-alanineCalciumdi-β-alaninat3-Maleimidopropionic acidPantothenic acid calcium salt monohydrateH-beta-Ala-OtBu HClEthyl 3-(isopropylamino)propanoateBenfuracarbCalciumpantothenat , D-Form2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamideL-AlaninPentagastrin5-Chloro-1H-indazole-3-carboxylic acidDisperse Blue 148(3-Amino-1-hydroxypropyliden)bisphosphonsureN-hydroxyethyl-N-hydroxyalkyl-β-alanineN-(tert-Butoxycarbonyl)-4-piperidoneethyl 3-(chlorosulfanyl-propan-2-yl-amino)propanoateD-Pantothensure3-aminopropanal

Ergänzende Hinweise

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