Basic information
- CAS
62-57-7- Standard SMILES
CC(C)(N)C(=O)O- InChIKey
FUOOLUPWFVMBKG-UHFFFAOYSA-N- Molecular formula
- C4H9NO2
- Average molar mass
- 103.12 g/mol
- Monoisotopic mass
- 103.06332853
Overview
2-aminoisobutyric acid is a rare, non-protein amino acid and end-product of pyrimidine metabolism, excreted in urine and found in some antibiotics of fungal origin. With the exception of a few bacteria, it is non-metabolisable, and therefore used in bioassays. It is functionally related to an isobutyric acid and a propionic acid. It is a tautomer of a 2-aminoisobutanoic acid zwitterion.
Names & identifiers
- Preferred name
- Aminoisobutyric acid
- IUPAC
- 2-amino-2-methylpropanoic acid
- English name
- 2-Aminoisobutyric Acid
- Molecular formula
- C4H9NO2
- Molecular weight
- 103.12
Names & synonyms
2-Aminoisobutyric acid62-57-72-Amino-2-methylpropanoic acidALPHA-AMINOISOBUTYRIC ACIDAlanine, 2-methyl-alpha-Methylalaninealpha-Aminoisobutanoic acidalpha,alpha-DimethylglycineAminoisobutyric acid1E7ZW41IQUCB 1637CHEBI:27971
Show more names
AIBAib-OHL-Aib-OHN-ME-ALA-OHN-ME-ALANINE
NSC-16590RefChem:465156200-544-02-MethylalanineH-Aib-OH2-Amino-2-methylpropionic acidNSC 16590a-Aminoisobutyric acid
Database identifiers
- CAS
62-57-7- PubChem CID
- 6119
- DTXSID
DTXSID0058772- ChEMBL
CHEMBL1230906- ChEBI
CHEBI:27971- UNII
- 1E7ZW41IQU
- EC Number
- 200-544-0
- Nikkaji
- J38.908K
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 63.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 87.7
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Amino Carboxylic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110]
Solubility181 mg/mL at 25 °C
Melting Point335 °C
Physical Description
Solid; [Merck Index] White solid; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
123.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
129 Ų [M-H]-
Physicochemical properties
- Melting point
- 300 °C · ≥300 °C
- Boiling point
- 193.35 °C · 193.35°C (rough estimate)
- Density
- 1.1602 · 1.1602 (rough estimate)
- refractive index
- 1.4183 · 1.4183 (estimate)
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Very easily soluble in water, poorly soluble in alcohol, insoluble in oils.
- pka
- 2.36 · 2.36(at 25℃)
- form
- Crystalline Powder
- color
- White
- Odor
- Practically odorless in the dry state
- Water Solubility
- SOLUBLE
- Merck
- 14 · 14,445
- BRN
- 506496 · 506496
- Major Application
- peptide synthesis
- InChI
- 1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)
- InChIKey
- FUOOLUPWFVMBKG-UHFFFAOYSA-N
- SMILES
- CC(C)(N)C(O)=O
- LogP
- -0.163 · -0.163 (est)
- CAS DataBase Reference
- 62 · 62-57-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 E7ZW41IQU · 1E7ZW41IQU
- NIST Chemistry Reference
- «alpha»-Aminoisobutanoic acid(62-57-7)
- EPA Substance Registry System
- 2 · Alanine, 2-methyl- (62-57-7)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- RTECS
- 7000000 · AY7000000
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29224995 · 29224995
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Eye Irrit. 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 6.3% (4 of 63) of reports.
Warning
H319 (93.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 63 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Alanine, 2-methyl-
Status: Active Update: 21-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30036
Alanine, 2-methyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryIntraperitoneal LD50 (mouse) = 750 mg/kg; [RTECS] May cause irritation; [Sigma-Aldrich MSDS] See (1)-3-Amino-2-methylpropionic acid.
Hazard Classes and CategoriesEye Irrit. 2A (93.7%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AY7000000
- hs_code
- 29224995
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Pharmacology
Tissue LocationsProstate
Cellular LocationsCytoplasm
Uses & manufacturing
General Manufacturing InformationAlanine, 2-methyl-: ACTIVE
Applications
Description2-Aminoisobutyric acid, also known as alpha-methylalanine or a-aminoisobutanoate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2-Aminoisobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Aminoisobutyric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2-Aminoisobutyric acid has been detected, but not quantified in, milk (cow). This could make 2-aminoisobutyric acid a potential biomarker for the consumption of these foods. Aminoisobutyric acid is a nonprotein amino acid (is an end product of pyrimidine metabolism) excreted in the urine of about 5% of healthy individuals , and high excretion is an autosomal recessive phenotype.
Uses2-Aminoisobutyric Acid inotransferases which can be used as a diagnostic tool to predict type II diabetes.
Uses2-Aminoisobutyric acid is a non- protein amino acid present in some antibiotics. It acts as a strong helix inducer in peptides. It is non-metabolisable used in bioassays.
Preparation methods
Preparationα-Aminoisobutyric Acid is prepared from Acetone (Blatt: Org. Synth. CoIl. vol. H, page 29, 1943) or by the Bucherer method (Org. Synth. vol. XX, 1940, page 42).
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A rare, non-protein amino acid and end-product of pyrimidine metabolism, excreted in urine and found in some antibiotics of fungal origin. With the exception of a few bacteria, it is non-metabolisable, and therefore used in bioassays.
Related reactions
172 records
Compound notes
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