DL-Alanine
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DL-Alanine

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Alanine (abbreviated as Ala or A; encoded by the codons GCU, GCC, GCA, and GCG) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated -NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated -COO- form under biological conditions), and a side chain methyl group, classifying it as a nonpolar (at physiological pH), aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it.The L-isomer (left-handed) of alanine is one of the 20 amino acids encoded by the human genetic code. L-Alanine is second only to leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins. The right-handed form, D-Alanine occurs in bacterial cell walls and in some peptide antibiotics.

Category
DL-Amino Acids
Catalog number
BAT-003580
CAS number
302-72-7
Molecular Formula
C3H7NO2
Molecular Weight
89.09
DL-Alanine
IUPAC Name
2-aminopropanoic acid
Synonyms
DL-Ala-OH; (R,S)-2-Aminopropionic acid
Appearance
White crystalline powder
Purity
98.5-101.0% (Assay by titration)
Density
1.424 g/cm3
Melting Point
289 °C (dec.)
Boiling Point
212.9±23.0 °C(Predicted)
Storage
Store at RT
InChI
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)
InChI Key
QNAYBMKLOCPYGJ-UHFFFAOYSA-N
Canonical SMILES
CC(C(=O)O)N

DL-Alanine, a racemic mixture encompassing the D- and L-forms of alanine, an amino acid with diverse roles in both biology and industry. Here are the key applications of DL-Alanine presented with a high degree of perplexity and burstiness:

Nutritional Supplements: Embarking on its journey in the realm of dietary supplements, DL-Alanine contributes its prowess in offering amino acid support to athletes and individuals with heightened protein requirements. Its role extends to bolstering muscle strength and endurance through its involvement in protein synthesis. Moreover, it acts as a swift energy source during prolonged physical exertions, enhancing the performance of individuals striving for athletic excellence.

Pharmaceuticals: Within the pharmaceutical sphere, DL-Alanine emerges as a pivotal building block in the creation of diverse drugs and medicinal concoctions. Its significance transcends into the synthesis of peptides and serves as a fundamental component in select therapeutic agents. Leveraging its buffer properties, DL-Alanine finds utility in drug delivery systems to maintain stable pH levels, ensuring the efficacy and safety of pharmaceutical formulations.

Food Industry: Stepping into the domain of the food industry, DL-Alanine assumes the role of a flavor enhancer and a contributor to improved nutritional profiles. Widely incorporated in various food products, it enhances the sweet flavors of delicacies without introducing excess calories. Its integration also aids in fortifying processed foods, rendering them more balanced and health-conscious, catering to the evolving dietary preferences of consumers.

Biochemical Research: In the intricate landscape of biochemical research, DL-Alanine stands as a cornerstone, serving as a standard in amino acid analysis and protein quantification. Researchers rely on its presence to calibrate instruments and verify analytical methods for exploring amino acid compositions. This indispensable tool plays a crucial role in deciphering metabolic pathways and unraveling protein interactions within diverse biological samples, enabling significant advancements in the field of biochemistry.

1. Terahertz response of DL-alanine: experiment and theory
T J Sanders, J L Allen, J Horvat, R A Lewis Phys Chem Chem Phys. 2021 Jan 6;23(1):657-665. doi: 10.1039/d0cp05432a.
The terahertz (THz) spectrum of dl-alanine has been measured for the first time at cryogenic temperatures and with a pure sample. Several sharp absorptions are observed, over a wide frequency range (0.8-4.8 THz), at 8 K. The sample structure and purity were confirmed with both Raman spectroscopy and X-ray diffraction. Temperature dependent spectra revealed redshifting, with increasing temperature, for all modes except one at 2.70 THz. This mode exhibits blueshifting until ≈120 K, where it starts to redshift. A Bose-Einstein distribution has been used to model the frequency shift with temperature for the four lowest energy modes. Strong correlations between the fits and data indicate that these modes are caused by phonon excitation in an anharmonic potential. Density functional theory has also been used to identify the origin of these low frequency modes. They are attributed to large scale molecular vibrations.
2. dl-Alanine Covalently Bonded Giant Arsenotungstate with Rapid Photochromic and Decent Proton Conduction Properties
Kangting Zheng, Dongsheng Yang, Bingxue Niu, Yajing Ye, Pengtao Ma, Jingping Wang, Jingyang Niu Inorg Chem. 2022 Dec 19;61(50):20222-20226. doi: 10.1021/acs.inorgchem.2c03494. Epub 2022 Dec 8.
A dl-alanine covalently bonded giant arsenotungstate, namely, Na3Ba11H16[(AsW9O33)6{W2O5(H2O)(dl-Ala)}2{W3O6(H2O)(dl-Ala)}2{W2O5(dl-Ala)}] (1; dl-Ala = dl-alanine), has been synthesized and is composed of six [AsW9O33]9- fragments fused together via two [W2O5(H2O)(dl-Ala)]+ segments, two [W3O6(H2O)(dl-Ala)]5+ segments, and a [W2O5(dl-Ala)]+ segment. This complex represents the first carboxylate-based hybrid polyoxotungstate without the introduction of lanthanide ions. Besides, compound 1 demonstrates not only fast photochromic properties but also interesting proton conductivity properties, with an achieved conductivity of 2.830 × 10-4 S·cm-1 (65 °C, 75% relative humidity).
3. DL-Alanine
M Subha Nandhini, R V Krishnakumar, S Natarajan Acta Crystallogr C. 2001 May;57(Pt 5):614-5. doi: 10.1107/s010827010100261x. Epub 2001 May 15.
A determination of the structure of the title compound, C3H7NO2, leads to an accurate description of its molecular dimensions and crystal packing. As in the structure of the L-isomer, the molecules aggregate into alternating layers, each consisting of only one type of isomer. The molecules in each layer are interconnected through head-to-tail sequences generated by a cell translation and a 2(1) screw axis. Adjacent layers are interconnected by head-to-tail sequences generated by a glide plane.
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