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Histidine

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Identification
Molecular formula
C6H9N3O2
CAS number
71-00-1
IUPAC name
(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
State
State

Histidine is typically a solid at room temperature, usually presented in the form of powder or crystalline flakes.

Melting point (Celsius)
282.00
Melting point (Kelvin)
555.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
155.16g/mol
Molar mass
155.1560g/mol
Density
1.4000g/cm3
Appearence

Histidine appears as a colorless to white crystalline solid. It is typically found in its zwitterionic form and is often crystallized from water in its anhydrous state.

Comment on solubility

Solubility of (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid

The compound (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid, with the chemical formula C6H9N3O2, exhibits noteworthy solubility characteristics that are worth discussing.

General Solubility Insights

This compound can be categorized as a zwitterionic amino acid derivative, which typically influences solubility in various solvents. The presence of both hydrophilic functional groups and a hydrophobic side chain plays a crucial role in determining its solubility.

Solubility in Water

Hydrophilic compounds, particularly those containing carboxyl and amino groups, tend to be soluble in water. In the case of (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid:

  • High Affinity for Water: The carboxylic acid functional group contributes to a significant degree of interaction with water molecules.
  • Ionic Interactions: The zwitterionic nature allows the molecule to interact favorably with polar solvents like water, leading to good solubility.

Solubility in Organic Solvents

When it comes to solubility in organic solvents, the following points are essential:

  • Limited Solubility: Due to its polar nature, (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid shows limited solubility in nonpolar organic solvents.
  • Biphasic Behavior: It may exhibit variable solubility in protic organic solvents, depending on the solvent's polarity and ability to form hydrogen bonds.

Conclusion

In summary, (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid displays:

  • Good solubility in water, thanks to its polar functional groups.
  • Limited solubility in nonpolar solvents, illustrating the classic principle of "like dissolves like."

Thus, understanding the solubility profile of this compound is essential for its application in various fields, including pharmaceuticals and biochemistry.

Interesting facts

Exploring (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid

(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid, commonly known as Histidine, is a fascinating amino acid that plays a vital role in biological systems. Here are some intriguing facts about this compound:

  • Essential Amino Acid: Histidine is classified as an essential amino acid for infants, meaning that it must be obtained through dietary sources, whereas adults can synthesize it.
  • Biological Roles: This amino acid is crucial for various physiological functions, including:
    • Protein synthesis
    • Enzymatic catalysis, particularly through histidine residues acting as proton donors or acceptors in enzymes
    • Production of histamine, a key mediator in immune responses and gastric acid secretion
  • Buffering Agent: Due to its unique side-chain properties, histidine can effectively act as a buffer in physiological pH ranges, helping to maintain acid-base balance in the body.
  • Imidazole Ring: The presence of the imidazole group in its structure allows histidine to participate in important biochemical reactions, particularly in enzyme active sites.
  • Food Sources: Rich sources of histidine include meat, fish, poultry, nuts, seeds, and dairy products, making it easy for most individuals to ensure their requirements are met.

In summary, (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid is not just a simple building block of proteins but also a compound with significant biological implications. As a compound that embodies the connection between nutrition and metabolic processes, histidine continues to be a subject of interest in both chemistry and biochemistry.

Synonyms
L-histidine
histidine
71-00-1
H-His-OH
glyoxaline-5-alanine
Anti-rheuma
histidina
Istidina
L-(-)-Histidine
S-Histidine
(L)-Histidine
Histidinum
HISTIDINE, L-
(S)-4-(2-Amino-2-carboxyethyl)imidazole
Histidine (VAN)
FEMA No. 3694
(2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid
L-Histidin
(S)-alpha-amino-1H-imidazole-4-propanoic acid
Histidine [USAN:INN]
Histidinum [INN-Latin]
4-(2-Amino-2-carboxyethyl)imidazole
(S)-Histidine
his
Histidina [INN-Spanish]
L-beta-(4-Imidazolyl)alanin
(S)-2-Amino-3-(4-imidazolyl)propionsaeure
L-hystidine
HSDB 1810
1H-Imidazole-4-alanine, (S)-
L-Hisidine
AI3-26558
7006-35-1
EINECS 200-745-3
L-beta-(4-Imidazolyl)-alpha-alanin
MFCD00064315
(S)-alpha-Amino-1H-imidazole-4-propionic acid
L-His
L-Alanine, 3-(1H-imidazol-4-yl)-
NSC 137773
UNII-4QD397987E
CHEBI:15971
L-His-OH
L-Histidine Base
alpha-Amino-4(or 5)-imidazolepropionic acid
Histidine (L-Histidine)
4QD397987E
NSC-137773
alpha-Amino-1H-imidazole-4-propionic acid, (S)-
1H-Imidazole-4-propanoic acid, alpha-amino-, (S)-
(S)-a-Amino-1H-imidazole-4-propanoic acid
DTXSID9023126
(S)-2-Amino-3-(4-imidazolyl)propionic acid
(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
HISTIDINE (II)
HISTIDINE [II]
Histidinum (INN-Latin)
Histidina (INN-Spanish)
HISTIDINE (MART.)
HISTIDINE [MART.]
(2S)-2-amino-3-(imidazol-4-yl)propanoic acid
HISTIDINE (EP MONOGRAPH)
HISTIDINE [EP MONOGRAPH]
HISTIDINE (USP MONOGRAPH)
HISTIDINE [USP MONOGRAPH]
Histidine, monohydrochloride
CHEBI:27570
NSC137773
1hsl
1lag
[3H]histidine
Histidine,(S)
[3H]-histidine
(2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid hydrochloride
Histidine (USP/INN)
HISTIDINE [INN]
L-Histidine (Standard)
HISTIDINE [MI]
L-Histidine (JP18)
L-2-Amino-3-(4-imidazolyl)propionic acid
HISTIDINE [HSDB]
HISTIDINE [USAN]
HISTIDINE [VANDF]
Lopac-H-8125
bmse000039
bmse000976
bmse001015
L-HISTIDINE [FCC]
L-HISTIDINE [JAN]
L-Histidine (H-His-OH)
amino-4-imidazoleproprionate
HISTIDINE [WHO-DD]
L-HISTIDINE [FHFI]
SCHEMBL3259
Lopac0_000566
US9138393, Histidine
US9144538, Histidine
(S)1H-Imidazole-4-alanine
CHEMBL17962
L-HISTIDINE [USP-RS]
(S)-1H-Imidazole-4-alanine
BDBM7953
DTXCID503126
GTPL3310
GTPL4670
L-Histidine, non-animal source
Imidazole C-4(5) deriv. 5
amino-4-imidazoleproprionic acid
amino-1H-imidazole-4-propanoate
HY-N0832R
Treating Periodontitis Toothpaste
L-Histidine, p.a., 98.5%
BDBM181118
3-(1H-imidazol-4-yl)-L-Alanine
HY-N0832
amino-1H-imidazole-4-propanoic acid
AKOS015854051
AKOS026676613
CCG-204656
CS-7781
DB00117
FH15651
SDCCGSBI-0050549.P002
SERINE IMPURITY C [EP IMPURITY]
(S)-a-Amino-1H-imidazole-4-propanoate
NCGC00015518-01
NCGC00162189-01
NCGC00162189-02
NCGC00162189-05
AC-35086
AS-14171
CAREDO Treating Periodontitis Toothpastes
DA-64956
(S)-alpha-Amino-1H-imidazole-4-propanoate
(S)-alpha-Amino-1H-imidazole-4-propionate
L-Histidine, BioUltra, >=99.5% (NT)
H0149
L-Histidine, SAJ special grade, >=98.5%
NS00074195
S3989
EN300-57334
(S)-2-Amino-3-(imidazol-4-yl)propanoic acid
C00135
CAREDO Treating Periodontitis Toothpastes100g
D00032
D70843
L-Histidine, ReagentPlus(R), >=99% (TLC)
M02982
L-Histidine, Vetec(TM) reagent grade, >=99%
(S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid
Q485277
B81AEDB0-EACA-4296-9BAB-52D60F137FFB
1H-Imidazole-4-propanoic acid, .alpha.-amino-, (S)-
F8881-8926
F8889-0575
L-Histidine, certified reference material, TraceCERT(R)
Z359369984
Histidine, European Pharmacopoeia (EP) Reference Standard
L-Histidine, United States Pharmacopeia (USP) Reference Standard
L-Histidine, Pharmaceutical Secondary Standard; Certified Reference Material
200-745-3
L-Histidine, cell culture tested, meets EP, USP testing specifications, from non-animal source