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HomeProduct name listHomoarginine

Homoarginine

  • CAS NO.:156-86-5
  • Empirical Formula: C7H16N4O2
  • Molecular Weight: 188.23
  • MDL number: MFCD00237108
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Homoarginine Structural

What is Homoarginine?

Description

Homoarginine and 1-hydroxyhomoarginine were originally detected in significant concentration in the seeds of many Lathyrus species (Bell, 1962a,b; 1963). Homoarginine was isolated from the seeds of L. cicera (Bell, 1962b) and L. sativus (Rao et al., 1963). The hydroxy compound was obtained from the seeds of L. tingitanus (Bell, 1964). The comparative distribution of guanidino compounds in the seeds of two genus of the Papilionoideae, Lathyrus and Vicia, exhibits interesting features (Bell and Tirimanna, 1964). For example, the genus Lathyrus stores predominantly the C7 amino acids homoarginine, y-hydroxyhomoarginine and the related compound lathyrine, while the genus Vicia stores relatively high concentrations of canavanine and of the C6 amino acids arginine and y-hydroxyarginine. Apart from plants, homoarginine was found in small amounts in human body fluids ,. urine (Armstrong, 1967), serum (Matsumoto et al., 1976a) and cerebrospinal fluid (Mori et al., 1981b) and in mammalian brain (Mori et al., 1978, 1979 ). Increased urinary excretion was reported in hyperlysinemia (Armstrong and Robinow, 1967) and citrullinemia (Scott-Emuakpor et al., 19(2).
Homoarginine may be formed in mammals from lysine, by a homologous urea cycle in which arginine is replaced by lysine (Ryan and Wells, 1964; Scott-Emuakpor et al., 19(2). The excretion of homocitrulline and homoarginine in urine following administration of lysine to children supports this theory (Buergi et al., 1966). The biosynthesis of homoarginine has not been examined in plants, but y-hydroxyhomoarginine is synthesized from homoarginine in Lathyrus seeds (Bell, 1964). Subsequently both compounds have been identified as the precursors of the cyclic guanidino derivative, lathyrine, also present in Lathyrus seeds (Bell and Przybylska, 1965). Homoarginine and y-hydroxyhomoarginine probably serve as nitrogen reserves in Lathyrus seeds.
Inhibition of growth by homoarginine has been reported In various microorganisms (Walker, 1955; Rao et al., 1963).
gama-Hydroxyhomoarginine lactone isolated from the seeds of L. tingitanus (Bell, 1964) probably results from the cyclization of the open chain compound under acidic conditions.

Chemical properties

White to off-white powder

The Uses of Homoarginine

Homoarginine as marker for exogenous protein
Absorption and secretion of free homoarginine in the intestine: when 9 mmol homoarginine were infused into the proximal part of the jejunum, there was a 99.9% disappearance of the free amino acid homoarginine up to the ileum. In addition, following the infusion of 9 mmol homoarginine into the vena jugularis less than 0.2% of the infused homoarginine appeared in the intestine.
We concluded from these data that with the homoarginine method endogenous protein in the chyme of the intestine can be distinguished from the food protein as homoarginine is not incorporated into endogenous secreta and free homo arginine is completely absorbed.

The Uses of Homoarginine

Homoarginine is an inhibitor of human arginase activity.

Definition

ChEBI: An L-lysine derivative that is the L-enantiomer of homoarginine.

Properties of Homoarginine

Melting point: 207-209 °C
Boiling point: 376.3±52.0 °C(Predicted)
Density  1.39±0.1 g/cm3(Predicted)
storage temp.  Keep in dark place,Inert atmosphere,2-8°C
solubility  Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form  Powder
pka 2.52±0.24(Predicted)
color  White to off-white
CAS DataBase Reference 156-86-5(CAS DataBase Reference)

Safety information for Homoarginine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H332:Acute toxicity,inhalation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P330:Rinse mouth.
P363:Wash contaminated clothing before reuse.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P501:Dispose of contents/container to..…

Computed Descriptors for Homoarginine

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