(2S)-2-aminopropanoic acid

• ChemBase ID: 46
• Molecular Formular: C3H7NO2
• Molecular Mass: 89.09318
• Monoisotopic Mass: 89.04767847
• SMILES: OC(=O)[C@@H](N)C
• Canonical SMILES: C[C@@H](C(=O)O)N
• InChI: InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
• InChIKey: QNAYBMKLOCPYGJ-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-aminopropanoic acid
• IUPAC Traditional name: L-alanine
• Synonyms: (S)-2-Aminopropionic acid; L-α-Aminopropionic acid; L-2-AMINO-1-PROPANOL; (2S)-2-Aminopropanoic acid; (S)-(+)-Alanine; (S)-2-Aminopropanoic acid; (S)-Alanine; 2-Aminopropanoic acid; 2-Aminopropionic acid; a-Alanine; a-Aminopropionic acid; Alanine; L-(+)-Alanine; L-2-Aminopropanoic acid; L-2-Aminopropionic acid; L-a-Alanine; L-a-Aminopropionic acid; ALA; L-Alanine; L-Alanine; L-ALANINE U.S.P.; A; L-α-ALANINE; H-Ala-OH; (S)-2-氨基丙酸; L-α-氨基丙酸; L-丙氨酸; L-丙胺酸

Database IDs

• CAS Number: 56-41-7; 2749-11-3
• EC Number: 200-273-8
• MDL Number: MFCD00064410
• Beilstein Number: 1720248
• Merck Index: 14204
• PubChem SID: 24891260; 24901893; 46504866; 160963509; 24891241; 24890849
• PubChem CID: 5950
• FEMA ID: 3818
• Flavis Number: 17.002

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4748974
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.840927
• LogD (pH = 7.4): -2.843974
• Log P: -2.840788
• Molar Refractivity: 20.4973 cm^3
• Polarizability: 8.358352 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.05
• LOG S: 0.7
• Solubility (Water): 4.47e+02 g/l

PROPERTIES

Physical Property

• Solubility: 164 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; H2O: soluble100 mg/mL
• Apperance: powder
• Melting Point: >297°C; ca 295°C dec.
• Density: 1.40 g/ml; 1.432
• Optical Rotation: [α]20/D +13.5 to +15.5°, c = 10 in 6 M HCl; [α]20/D +13.5±1°, c = 5% in 5 M HCl; [α]20/D +14.5°, c = 10 in 6 M HCl; +14 (c=5 in 5N HCl)
• Hydrophobicity(logP): -2.8

Safety Information

• Storage Condition: Room Temperature (15-30°C); Room Temperature (15-30°C), Protect from light
• Storage Warning: IRRITANT
• RTECS: AY2990000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 20-25°C

Pharmacology Properties

• Gene Information: human ... CA1(759), CA2(760)

Product Information

• Purity: ≥98% (TLC); ≥98.0% (NT); ≥98.5%; ≥99%; ≥99.0%; 98%; 98.5%; 99%
• Grade: certified reference material; EP; PharmaGrade; purum; SAJ special grade; TraceCERT®; USP
• Optical Purity: ee: 99% (GLC)
• Suitability: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Impurities: endotoxin, tested
• Biological Source: from non-animal source
• Loss on Drying: ≤0.5% loss on drying
• Quality Level: GMP-COMPENDIA
• Empirical Formula (Hill Notation): C3H7NO2

DETAILS

MP Biomedicals - 05203557

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02194617

Cell Culture Reagent
Crystalline

MP Biomedicals - 02100287

Crystalline
Purity: 98.5%

DrugBank - DB00160

• Drug Groups: approved; nutraceutical
• Description: 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. [PubChem]
• Indication: Used for protein synthesis.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals

Sigma Aldrich - A4349

Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - A7469

包装
10 mg in autosmp vl
Biochem/physiol Actions
L-Alanine is a nonessential amino acid which is highly concentrated in muscle. It is a key player in the Glucose-Alanine cycle, which enables the removal of pyruvate and glutamate from muscle to the liver. Once in the liver, glucose is regenerated from pyruvate and returned to the muscle while glutamate ultimately participates in the urea cycle to form urea. The Glucose-Alanine cycle aides to conserve ATP in muscle for muscle contraction, while the energy burden of gluconeogenesis is imposed upon the liver.

Sigma Aldrich - A7627

包装
1 g in poly tube
1 kg in poly bottle
100, 500 g in poly bottle
Biochem/physiol Actions
Alanine is a nonessential amino acid that plays a key role in the glucose-alanine cycle between muscle tissue and the liver. In amino acid-degrading tissues such as muscle, amino groups are pooled as glutamate by transamination reactions. The amino group of glutamate is transferred to pyruvate via alanine aminotransferase, forming alanine and α-ketoglutarate. The alanine is passed into the blood and transported to the liver. This reaction is reversed in the liver where pyruvate can be used in gluconeogenesis to form glucose, which may return to other tissues through the circulatory system. Increased alanine levels correlate with higher blood pressure, energy intake, cholesterol levels, and body mass index.

Sigma Aldrich - A26802

Packaging
25 g in poly bottle

Sigma Aldrich - W381829

Packaging
1 kg in poly bottle
100 g in poly bottle

Sigma Aldrich - 44526

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• ɑ-Amino acids can be converted to the corresponding ɑ-chloro acids with a high degree of retention of configuration, by diazotization in the presence of HCl: J. Am. Chem. Soc., 76, 6054 (1954). The intermediate is thought to be a rigid oxiranone which prevents racemization. For an improved technique and list of examples, see: Org. Synth. Coll., 8, 119 (1993):