DL-Asparagine
Basic information
- CAS
3130-87-8- Standard SMILES
NC(=O)CC(N)C(=O)O- InChIKey
DCXYFEDJOCDNAF-UHFFFAOYSA-N- Molecular formula
- C4H8N2O3
- Average molar mass
- 132.12 g/mol
- Monoisotopic mass
- 132.05349212
Overview
Asparagine is an alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group. It has a role as a Daphnia magna metabolite and an algal metabolite. It is a polar amino acid, an alpha-amino acid and a dicarboxylic acid monoamide. It contains a 2-amino-2-oxoethyl group. It is a conjugate base of an asparaginium. It is a conjugate acid of an asparaginate.
Names & identifiers
- Preferred name
- DL-Asparagine
- IUPAC
- 2,4-diamino-4-oxobutanoic acid
- English name
- DL-Asparagine monohydrate
- Molecular formula
- C4H8N2O3
- Molecular weight
- 132.12
Names & synonyms
DL-AsparagineASPARAGINE, DLDTXSID30859927NSC 7891EINECS 221-521-1NSC 206243DLAspartamineRefChem:589923DTXCID901972764-amino-2-azaniumyl-4-oxobutanoate3130-87-8Asparagine, DL-
Show more names
DL-AsnASPARAGINEh-dl-asn.hDL-Asn.H2ODL-AspartamineAsparagine,99%DL-Asparagine.H2O
H-DL-Asn-OH2-amino-3-carbamoyl-propanoic acid7006-34-0NSC7891D(-)-Asparagine monohydrateasparaginH-Asn-OH HOWLN: ZV1YZVQ
Database identifiers
- CAS
3130-87-8、70-47-3- PubChem CID
- 236
- DTXSID
DTXSID30859927- ChEBI
CHEBI:22653- Nikkaji
- J1.289K
Properties
Computed structural properties
- XLogP
- -3.4
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 134
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
Physical DescriptionMonohydrate: White crystalline powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 220 °C · 220 °C (dec.)(lit.)
- Boiling point
- 438 · 438.0±40.0 °C(Predicted)
- Density
- 1.404 · 1.404±0.06 g/cm3(Predicted)
- storage temp.
- Room Temperature
- solubility
- Aqueous Acid (Slightly), Water (Slightly)
- pka
- 2.17 · 2.17(at 20℃)
- form
- Fine Crystalline Powder
- color
- White
- Water Solubility
- soluble
- BRN
- 6234992 · 6234992
- Major Application
- peptide synthesis
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationChemical: DL-Asparagine
Other Safety InformationIMAP assessments - DL-Asparagine: Environment tier I assessment
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29241900
- risk_code
- 20/21/22-36/37/38
- hazard_code
- Xn
- safety_code
- 24/25-36-26
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Uses & manufacturing
UsesAsparagine is a non-essential amino acid; [Merck Index]
Applications
UsesDL-asparagine is a racemic mixture of the non-essential amino acids, L and D-aparagine. It is generally used in growth-media for bacteria-growth. DL-Asparagine monohydrate can also be used to synthesize other salts such as DL-asparaginium perchlorate, DL-asparaginium nitrate and dimethyl DL-aspartate.
Preparation methods
PreparationDL-Asparagine monohydrate was synthesized by dissolving maleic anhydride in 1,4-dioxane solution and refluxing with benzylamine after ammonolysis, followed by catalytic hydrogenation.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.
Related reactions
15 records
Compound notes
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