5794-13-8

Basic information

• Product Name: L(+)-Asparagine monohydrate
• Synonyms: ASPARAGINIC ACID SEMIAMIDE;ASPARAGINIC ACID SEMIAMIDE MONOHYDRATE;ASPARAGINE MONOHYDRATE;ASPARAGINE H2O;H-ASN-OH H2O;H-L-ASN-OH H2O;L-ALPHA-AMINOSUCCINAMIC ACID, MONOHYDRATE;L-ASN H2O
• CAS NO: 5794-13-8
• Molecular Formula: C₄H₈N₂O₃*H₂O
• Molecular Weight: 150.13
• EINECS: 200-735-9
• Product Categories: Amino ACIDS SERIES;Asparagine [Asn, N];alpha-Amino Acids;Amino Acids;Biochemistry;L-Amino Acids;Amino Acids;amino
• Mol File: 5794-13-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 233-235 °C(lit.)
• Boiling Point: 271.66°C (rough estimate)
• Flash Point: 218.7 °C
• Appearance: White to Off-white/powder
• Density: 1,543 g/cm3
• Vapor Pressure: 2.68E-15mmHg at 25°C
• Refractive Index: 31 ° (C=10, HCl)
• Storage Temp.: Store at 0-5°C
• Solubility: H2O: 20 mg/mL
• Water Solubility: 30 g/L (20 ºC)
• Merck: 14,837
• BRN: 5767869
• CAS DataBase Reference: L(+)-Asparagine monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: L(+)-Asparagine monohydrate(5794-13-8)
• EPA Substance Registry System: L(+)-Asparagine monohydrate(5794-13-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: Y
• Hazardous Substances Data: 5794-13-8(Hazardous Substances Data)

Usage

Chemical Properties

White or almost white, crystalline powder or colourless crystals.

Uses

Different sources of media describe the Uses of 5794-13-8 differently. You can refer to the following data:
1. L-Asparagine is a naturally occurring amino acid that is not an essential for humans and can be synthesized from central metabolic pathway intermediates.
2. L-Asparagine is a naturally occurring proteinogenic amino acid, used in biomanufacturing cell culture systems for the production of therapeutic recombinant proteins and monoclonal antibodies. It is used in the biosynthesis of proteins. It is also required for development and function of the brain.

General Description

Asparagine biosynthesis is catalyzed by glutamine-dependent asparagine synthetase in mammalian tissues. Elevated levels of free asparagine is observed in plants facing stress in the form of drought or high salt. It is also present in senescing leaves and germinating seeds.

Biochem/physiol Actions

Asparagine has high nitrogen to carbon ratio and is a key regulator for nitrogen storage and transport. Its thermal degradation in the presence of sugars leads to the acrylamide formation in foods. Asparagine serves as an amino acid exchange factor and is essential for amino acid homeostasis. It favors cancer cell proliferation.

InChI:InChI=1/C27H18Cl3N3O/c28-21-7-1-18(2-8-21)16-31-23-11-5-20(6-12-23)27(34)33-26-14-13-24(15-25(26)30)32-17-19-3-9-22(29)10-4-19/h1-17H,(H,33,34)/b31-16+,32-17+

Synthetic route

dichloro(p-cymene)ruthenium(II) dimer + sodium methylate (124-41-4) + silver trifluoromethanesulfonate (2923-28-6) + L-asparagine monohydrate (5794-13-8) → {(η6-p-cymene)Ru(L-asparagine(1-))}CF3SO3*NaCF3SO3*H2O

Conditions	Yield
In methanol byproducts: AgCl; under Ar, dropwise addn. of NaOMe-soln. to Ru-compd. and ligand in methanol, stirred for 15 min at room temp., addn. of AgCF3SO3 in ethanol; evapd. in vac., residue taken up in CH2Cl2 and few methanol, dropwise addn. to ether, washed with pentane, dried in vac.; elem. anal.;	85%

N-(tert-butoxy)carbonyl-L-isoleucine N-hydroxysuccinimide ester (3392-08-3) + L-asparagine monohydrate (5794-13-8) → (S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-succinamic acid (90315-41-6)

Conditions	Yield
With triethylamine In 1,4-dioxane; water Ambient temperature; overnight;	68%

benzoyl chloride (98-88-4) + L-asparagine monohydrate (5794-13-8) → Nα-benzoyl-L-asparagine

Conditions	Yield
With potassium carbonate In water	68%

carbonyl(pentamethylcyclopentadienyl)cobalt diiodide + L-asparagine monohydrate (5794-13-8) → {(C5(CH3)5)Co(O2CCH(NH2)CH2C(O)NH2)}(1+)*I(1-)*1.5H2O={(C5(CH3)5)Co(O2CCH(NH2)CH2C(O)NH2)}I*1.5H2O

Conditions	Yield
With sodium methanolate In methanol Ar; stirred; 15 h;; centrifuged; layered with Et2O; crystd.; elem. anal.;;	30%

chlorothalonil (1897-45-6) + L-asparagine monohydrate (5794-13-8) → 4-N-L-Asparagyl-2,5,6-trichloro-1,3-dicyanobenzene

Conditions	Yield
With sodium carbonate In methanol; water

vanadyl sulfate trihydrate + L-asparagine monohydrate (5794-13-8) → L-asparagine monohydrate-VO(2+)

Conditions	Yield
In water prepn. by mixing aq. soln. of L-asparagine monohydrate and VOSO4*3H2O; soln. slowly evapd.;

L-Tartaric acid (87-69-4) + L-asparagine monohydrate (5794-13-8) → L-asparagine L-tartaric acid (108590-03-0)

Conditions	Yield
In water at 40℃;

Relevant articles and documents

Preparation of an asparagine or a glutamine

A process for the preparation of compounds of the general formula EQU1 (in which n is an integer equal to 1 or 2 and X and Y which may be the same or different are hydrogen atoms or organic groups, except that when n=2 not more than one of X and Y may represent a hydrogen atom) in which a compound of the general formula EQU2 (in which M+ represents a cation, R represents an aliphatic group containing 1 to 3 carbon atoms and X, Y and n have the meanings given above) is reacted with ammonia in an aqueous medium and thereafter the compound of formula (I) is liberated by acidification of the reaction medium.