Asparagine

InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
Key: DCXYFEDJOCDNAF-REOHCLBHSA-N
InChI=1/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
Key: DCXYFEDJOCDNAF-REOHCLBHBD

SMILES

O=C(N)C[C@H](N)C(=O)O
Zwitterion: O=C(N)C[C@H]([NH3+])C(=O)[O-]

Properties

Chemical formula

C₄H₈N₂O₃Molar mass132.119 g·mol Appearance white crystals Density1.543 g/cm Melting point234 °C (453 °F; 507 K) Boiling point438 °C (820 °F; 711 K)

Solubility in water

2.94 g/100 mL Solubilitysoluble in acids, bases, negligible in methanol, ethanol, ether, benzene log P−3.82 Acidity (pK_a)

2.1 (carboxyl; 20 °C, H₂O)
8.80 (amino; 20 °C, H₂O)

Magnetic susceptibility (χ)

−69.5·10 cm/mol Structure

Crystal structure

orthorhombic Thermochemistry

Std enthalpy of
formation(Δ_fH₂₉₈)

−789.4 kJ/mol Hazards NFPA 704 (fire diamond)

1

0

Flash point219 °C (426 °F; 492 K) Safety data sheet (SDS) Sigma-AlrichSupplementary data page Asparagine (data page)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify ( ?)

Asparagine (symbol Asn or N) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH
₃ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO form under biological conditions), and a side chain carboxamide, classifying it as a polar (at physiological pH), aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it. It is encoded by the codons AAU and AAC.

The one-letter symbol N for asparagine was assigned arbitrarily, with the proposed mnemonic asparagiNe;