4998-57-6

Basic information

• Product Name: DL-Histidine
• Synonyms: 1H-Imidazole-4-alanine;D-Histidine/L-histidine,(1:1);rac-(R*)-2-Amino-3-(4-imidazolyl)propionic acid;DL-Histidine,98%;DL-Histdine;H-DL-His-OH (DL-Histidine;DL-Histidine free base
• CAS NO: 4998-57-6
• Molecular Formula: C₆H₉N₃O₂
• Molecular Weight: 155.15
• EINECS: 225-660-9
• Product Categories: alpha-Amino Acids;Amino Acids;Biochemistry;Amino Acids
• Mol File: 4998-57-6.mol

Chemical Properties

• Melting Point: 273 °C (dec.)(lit.)
• Boiling Point: 278.95°C (rough estimate)
• Flash Point: 231.3 °C
• Appearance: white to slightly yellow crystalline powder
• Density: 1.3092 (rough estimate)
• Vapor Pressure: 3.25E-09mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Store at RT.
• Solubility: 0.5 M HCl: soluble
• PKA: 1.8(at 25℃)
• Merck: 14,4720
• BRN: 7800
• CAS DataBase Reference: DL-Histidine(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Histidine(4998-57-6)
• EPA Substance Registry System: DL-Histidine(4998-57-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36/37-26
• WGK Germany: 3
• Hazardous Substances Data: 4998-57-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DL-Histidine is used as a skin-conditioning agent for its beneficial effects on the skin, promoting healthy skin appearance and function.
Used in Membrane Research:
DL-Histidine is used as a research compound to study the fouling behavior of polyethersulfone ultrafiltration membranes made with different PVP (polyvinylpyrrolidone), which can help in the development of more efficient and durable filtration systems.
Used in Nutritional Supplements:
DL-Histidine is used as a dietary supplement to support the body's natural production of histamine, which plays a crucial role in immune response and other physiological functions.
Used in Food Industry:
DL-Histidine is used as a flavor enhancer and a component in the production of certain additives, taking advantage of its unique taste and properties.
Used in Cosmetics:
DL-Histidine is used as an ingredient in the cosmetics industry for its skin-conditioning properties, helping to improve skin health and appearance in various cosmetic products.

Synthesis Reference(s)

Journal of the American Chemical Society, 67, p. 502, 1945 DOI: 10.1021/ja01219a513Chemical and Pharmaceutical Bulletin, 35, p. 3447, 1987

Biochem/physiol Actions

L-Histidine is involved in the one-carbon unit metabolism. It is associated with protein methylation. L-Histidine is a part of hemoglobin structure and function. L-Histidine is a component of dipeptides with antioxidative property. Histidine serves as a precursor for the formation of histamine, which is associated with allergic responses. Urocanic acid, an immune response modulator in skin is also biosynthesised from histidine.

InChI:InChI=1/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)

Upstream product

• 71-00-1 L-histidine 
• 10101-30-1 N-acetylhistidine 
• 14056-33-8 2-(benzoylamino)-3-imidazol-4-ylpropanoic acid 
• 71-00-1 L-histidine 
• 108-24-7 acetic anhydride 
• 4998-57-6 His 
• 58942-05-5 5-[(4-imidazolyl)methyl]hydantoin 

Downstream Products

• 71-00-1 L-histidine 
• 351-50-8 D-histidin 
• 19728-57-5 C₁₄H₁₅N₃O₄ 
• 557-11-9 allylurea 
• 71-00-1 L-histidine 
• 71-00-1 D-histidine 
• 128424-98-6 C₁₅H₁₇N₇O₇ 
• 128425-10-5 C₁₅H₁₇N₇O₇ 
• 507-29-9 hercynine 

Relevant articles and documents

Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography

In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with open-tubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L9(34). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5?μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77?mmol·m?2. The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.

Chromatographic Resolution of α-Amino Acids by (R)-(3,3'-Halogen Substituted-1,1'-binaphthyl)-20-crown-6 Stationary Phase in HPLC

Three new chiral stationary phases (CSPs) for high-performance liquid chromatography were prepared from R-(3,3'-halogen substituted-1,1'-binaphthyl)-20-crown-6 (halogen = Cl, Br and I). The experimental results showed that R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one α-amino acids have different degrees of separation on R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-(1,1'-binaphthyl)-20-crown-6 derivatives. Both the separation factors (α) and the resolution (Rs) are better than those of commercial crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR(+). This study proves the commercial usefulness of the R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 chiral stationary phase.

INSULIN PREPARATIONS CONTAINING METHIONINE

The invention relates to an aqueous pharmaceutical formulation having insulin, an insulin analog, or an insulin derivative, and methionine; and to the production thereof, to the use thereof for treating diabetes mellitus, and to a medication for treating diabetes mellitus.

ANTIBIOFILM GLYCOPEPTIDES

The present invention relates to peptides and compositions that have antibiofilm properties. In particular, the peptides and compositions of the invention can be used for the treatment or prevention of various conditions including dental caries, gingivitis, periodontitis, oral mucositis, dry mouth and xerostomia.

NOVEL INSULIN DERIVATIVES HAVING AN EXTREMELY DELAYED TIME-ACTION PROFILE

The invention relates to novel insulin analogs having a basal time-action profile, which are characterized by the following features: a) the B chain end consists of an amidated basic amino acid residue such as lysine or arginine amide; b) the N-terminal amino acid residue of the insulin A chain is a lysine or arginine radical; c) the amino acid position A8 is occupied by a histidine radical; d) the amino acid position A21 is occupied by a glycine radical; and e) one or more substitutions and/or additions of negatively charged amino acid residues are carried out in the positions A5, A15, A18, B-1, B0, B1, B2, B3 and B4.

AGENT FOR PREVENTING/TREATING CANCER

A human monoclonal antibody against a protein comprising the same or substantially the same amino acid sequence as the amino acid sequence represented by SEQ ID NO: 1 or SEQ ID NO: 3, its partial peptide, or a salt thereof, is useful as an agent for preventing/treating cancer, etc., an apoptosis inducer of cancer cells, a growth inhibitor of cancer cells, a cytotoxic agent against cancer cells through a host defense mechanism mediated by the Fc region of an antibody, and so on.

Modulation of Glutamine Synthetase Activity

Methods of screening and designing compounds as inhibitors of glutamine synthetase are provided herein. Compounds, e.g., serine protease inhibitors, and compositions comprising the same, that are useful for the treatment, prevention, and/or amelioration of bacterial infections, including Mycobacterium tuberculosis, are also provided.

NEUROMEDIN U DERIVATIVE

The objective of the present invention is to provide a new antifeedant. The other objective of the present invention is to provide a NMU derivative showing a high antifeedant activity even in common administration forms such as peripheral administration. A neuromedin U derivative wherein a methoxypolyethylene glycol is bound via a linker having a specific structure to a polypeptide which contains at least 8 amino acids of the C-terminus of an amino acid sequence of neuromedin U and which consists of the same or substantially the same amino acid sequence as the amino acid sequence of neuromedin U.

SOLUBILITY TAGS FOR THE EXPRESSION AND PURIFICATION OF BIOACTIVE PEPTIDES

Peptide tags, referred to here as inclusion body tags, are disclosed useful for the generation of insoluble fusion peptides. The fusion peptides comprise at least one inclusion body tag operably linked to a peptide of interest. Expression of the fusion peptide in a host cell results in a product that is insoluble and contained within inclusion bodies in the cell and/or cell lysate. The inclusion bodies may then be purified and the protein of interest may be isolated after cleavage from the inclusion body tag.

Compositions and Methods for Binding Lysophosphatidic Acid

Compositions and methods for making and using anti-LPA agents, for example, monoclonal antibodies, are described.