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L-Citrulline

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Identification
Molecular formula
C6H13N3O3
CAS number
372-75-8
IUPAC name
(2S)-2-amino-5-ureido-pentanoic acid
State
State

At room temperature, L-Citrulline is typically in a solid state. It appears as a stable crystalline powder, which is common for amino acids outside of solution.

Melting point (Celsius)
214.00
Melting point (Kelvin)
487.00
Boiling point (Celsius)
451.00
Boiling point (Kelvin)
724.00
General information
Molecular weight
175.19g/mol
Molar mass
175.1880g/mol
Density
1.4020g/cm3
Appearence

L-Citrulline is a crystalline compound that is typically white or colorless. It is powdery in texture and can dissolve in water, producing a neutral solution. Commercial powdered forms of L-Citrulline are often used in supplements and can vary slightly in color depending on purity and the presence of additives.

Comment on solubility

Solubility of (2S)-2-amino-5-ureido-pentanoic acid

(2S)-2-amino-5-ureido-pentanoic acid, also known as L-arginine, showcases interesting solubility properties due to its ionic nature and polar functional groups. These characteristics influence its ability to dissolve in various solvents.

Key Solubility Characteristics:

  • Water Solubility: This compound is highly soluble in water, primarily because of its amino and urea groups that can form hydrogen bonds with water molecules.
  • Solvent Compatibility: In addition to water, (2S)-2-amino-5-ureido-pentanoic acid exhibits moderate solubility in polar organic solvents such as methanol and ethanol.
  • Temperature Considerations: Like many amino acids, its solubility typically increases with temperature, making warm solutions more effective for dissolving the compound.

It is notable that the solubility of (2S)-2-amino-5-ureido-pentanoic acid can also be influenced by pH. In acidic conditions, the compound can become protonated, thus affecting its solubility profile. In summary, its solubility is best described as:

"A compound with considerable water solubility due to its polar characteristics, allowing effective dissolution across varying conditions."

Understanding these solubility attributes is crucial for applications in biochemistry and pharmacology, where this compound is frequently utilized.

Interesting facts

Interesting Facts about (2S)-2-amino-5-ureido-pentanoic acid

(2S)-2-amino-5-ureido-pentanoic acid, commonly referred to as a derivative of the amino acid arginine, is a fascinating compound that plays a significant role in various biochemical processes. Here are some intriguing aspects of this compound:

  • Amino Acid Derivative: This compound incorporates an amine group, making it an essential building block in protein synthesis and metabolism.
  • Biological Significance: It is involved in the urea cycle, a crucial metabolic pathway in organisms that converts ammonia to urea, thus helping in the detoxification process.
  • Enzymatic Role: It serves as a substrate for various enzymes, impacting the regulation of different biochemical reactions in the body.
  • Research Applications: Scientists are actively studying its functions and potential applications in medicine, particularly in relation to metabolic disorders and nutritional supplements.
  • Structure-Activity Relationship: The specific configuration of its amino and urido groups contributes to its biological activity, making it an interesting subject for research into how structural changes affect function.

In summary, the study of (2S)-2-amino-5-ureido-pentanoic acid not only enhances our understanding of amino acid derivatives but also opens doors to advancements in health and nutrition. As the scientific community continues to explore the complexities of this compound, it may unveil new therapeutic avenues that leverage its unique properties.

Synonyms
L-citrulline
citrulline
372-75-8
H-cit-oh
delta-Ureidonorvaline
Sitrulline
N5-Carbamoyl-L-ornithine
(S)-2-Amino-5-ureidopentanoic acid
L-Cytrulline
Citrulline, L-
N(delta)-Carbamylornithine
N5-(Aminocarbonyl)ornithine
N5-carbamoylornithine
N5-(Aminocarbonyl)-L-ornithine
Ornithine, N5-(aminocarbonyl)-
L(+)-citrulline
alpha-Amino-delta-ureidovaleric acid
L-2-Amino-5-ureidovaleric acid
L-Ornithine, N5-(aminocarbonyl)-
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
2-Amino-5-ureidovaleric acid
MFCD00064397
L-citrullin
UNII-29VT07BGDA
EINECS 206-759-6
29VT07BGDA
NSC 27425
Ornithine, N5-carbamoyl-, L-
CHEBI:16349
Ngamma-carbamylornithine
N(5)-(aminocarbonyl)-L-ornithine
NSC-27425
N(5)-carbamoyl-L-ornithine
DTXSID80883373
cit
d-ureidonorvaline
gamma-ureidonorvaline
N(SUP 5)-(AMINOCARBONYL)-L-ORNITHINE
CITRULLINE (MART.)
CITRULLINE [MART.]
2-Amino-5-uredovaleric acid
CIR
L-CITRULLINE (USP-RS)
L-CITRULLINE [USP-RS]
L-(+)-Citrulline
(2S)-2-amino-5-(aminocarbonylamino)pentanoic acid
(2S)-2-Amino-5-(carbamoylamino)pentanoic Acid (Citrulline)
Ornithine, N5-carbamoyl-, L- (8CI)
N(5)-carbamoylornithine
N5-carbamylornithine
N~5~-carbamoyl-L-ornithine
Cytrulline
Ureidonorvaline
Ureidovalerate
H-Orn(carbamoyl)-OH;L-Citrulline
L-Citruline
gammaureidonorvaline
N-carbamylornithine
L-Citrulline, 4
Amino-ureidovalerate
ND-carbamylornithine
N()-carbamylornithine
L-Citrulline (DCF)
L-Citrulline, 98%
Ndelta-Carbamylornithine
starbld0002494
Amino-ureidovaleric acid
Ndelta-carbamy-ornithine
CITRULLINE [MI]
A-amino-d-ureidovalerate
L-Citrulline (Standard)
2-Amino-5-uredovalerate
2-Amino-5-ureidovalerate
L-N5-carbamoyl-Ornithine
CITRULLINE [VANDF]
bmse000032
bmse000800
bmse000858
CITRULLINE [WHO-DD]
A-amino-d-ureidovaleric acid
L-2-Amino-5-ureidovalerate
SCHEMBL20588
GTPL722
N5-(aminocarbonyl)-Ornithine
L-2-Amino-5-ureido-valerate
CHEMBL444814
Alpha-amino-delta-ureidovalerate
Alpha-amino-gamma-ureidovalerate
SCHEMBL13254095
BDBM92903
HY-N0391R
(S)-2-Amino-5-ureidopentanoate
L(+)-2-Amino-5-ureidovalerate
L-2-Amino-5-ureido-valeric acid
L-Citrulline, >=98% (TLC)
DTXCID301022909
HY-N0391
pentanoic acid, 2-amino-5-ureido-
L(+)-2-Amino-5-ureidovaleric acid
s3798
AKOS005259571
AKOS006240677
CCG-266398
CS-W019940
DB00155
FC15792
SMP1_000146
NCGC00142602-01
AC-23976
AS-12594
(2S)-2-amino-5-(carbamoylamino)pentanoate
(S)-2-amino-5-(aminocarbonyl)aminopentanoate
C00327
D07706
D71216
EN300-251063
M03230
(S)-2-amino-5-(aminocarbonyl)aminopentanoic acid
Q408641
L-2-AMINO-5-(CARBAMOYLAMINO)PENTANOIC ACID
EA65B21D-61C4-4748-9E9F-0CF6EDF9A21D
Z1198149761
(S)-2-Amino-5-ureidopentanoic acid,;L-2-Amino-5-ureidovaleric acid
L-Citrulline, United States Pharmacopeia (USP) Reference Standard
206-759-6