Chemical Properties
Arginine is a diaminomonocarboxylic acid. The nonessential amino acid, arginine, is a urea cycle amino acid and a
precursor for the neurotransmitter nitric oxide, which plays a role in the regulation of the brain’s system of dilation and constriction
of small blood vessels. It is strongly alkaline and its water solutions absorb carbon dioxide from the air (FCC, 1996). Functionality in
foods includes, but is not limited to, nutrient and dietary supplement
Chemical Properties
White crystalline powder
Physical properties
Solubility 14.87 (20 ℃) g/100 g H2O, pI 10.76, dissociation constants: pK1 2.01, pK2 9.04 (a-NH2), pK3 12.48 (guanidyl).
Occurrence
Reported present in cheese, chocolate, eggs, meat, nuts and other products.
Definition
ChEBI: An L-alpha-amino acid that is the L-isomer of arginine.
Aroma threshold values
Detection at 100%, faint.
Taste threshold values
Taste characteristics at 1000 ppm: hint of sourness.
General Description
L-Arginine is an amino acid that plays a key role in many physiological processes such as tissue repair and reproduction. It is a key precursor for synthesizing nitric oxide in mammals. Due to these factors, the dietary supplementation with L-arginine may show a range of health benefits.
Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Side effects
Nausea, abdominal pain and diarrhea
Bloating
Gout
Headache
Allergic response
Airway inflammation or worsening of asthma symptoms
Safety Profile
Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.
Synthesis
Enzymatically, arginine is formed in two reactions from citrulline. The first reaction (citrulline + succinate) is catalyzed
by the enzyme arginosuccinate synthetase. It is ATP dependent and with the formation of a new C–N bond in the gaunidino group of
arginosuccinate, water is removed and ATP is hydrolyzed. The second reaction is catalyzed by arginine synthetase and involves the
scission of arginosuccinate with the formation of arginine and fumaric acid.
target
NO | IL Receptor | cGMP
Drug interactions
L-arginine may interact with certain medications, including :
Blood-pressure-lowering medications: enalapril (Vasotec), losartan (Cozaar), amlodipine (Norvasc), furosemide (Lasix), etc.
Erectile dysfunction medications: sildenafil citrate (Viagra), tadalafil (Cialis), etc.
Blood-thinning medications: clopidogrel (Plavix), enoxaparin (Lovenox), heparin, warfarin (Coumadin), etc.
Antidiabetic medications: insulin, pioglitazone (Actos), glipizide (Glucotrol), etc.
Medications that increase blood flow: nitroglycerin (Nitro-Dur, Nitro-Bid, Nitrostat), isosorbide ( Sorbitrate, Imdur, Isordil), etc.
Diuretic medications: amiloride (Midamor), and triamterene (Dyrenium), spironolactone (Aldactone), etc.
Purification Methods
S-Arginine crystallises from H2O as the dihydrate and as plates from EtOH. It also crystallises from 66% EtOH. Its solubility in H2O is 15% at 21o. Its isoelectric point is at pH 10.76. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 1841 1961, Beilstein 4 IV 817.]
