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| Targets |
As a racemic mixture of histidine, H-DL-His-OH does not have a single specific biological target. L-Histidine is a precursor for histamine and is incorporated into proteins, while D-histidine can interact with D-amino acid oxidase and certain transporters. The compound is used to study the stereospecificity of histidine-metabolizing enzymes such as histidine decarboxylase and histidine ammonia-lyase, as well as amino acid transporters. In its racemic form, the compound is not designed to target a particular receptor or enzyme with high specificity, but rather serves as a tool to investigate stereochemical preferences in biological systems. Its value lies in its ability to provide both enantiomers for comparative studies.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro, H-DL-His-OH is used to study amino acid transport, metabolism, and enzyme kinetics. For example, it can be used as a substrate for histidine decarboxylase to measure the production of histamine, or for histidine ammonia-lyase to measure the production of urocanic acid. The racemic mixture allows researchers to compare the activity of these enzymes with the L-isomer alone. In cell culture, DL-histidine can be used to supplement media to study histidine uptake and its effects on cellular functions such as histamine production or protein synthesis. The compound does not have intrinsic pharmacological activity such as receptor agonism; its effects are mediated through its metabolism to histamine or through its incorporation into proteins. It is not cytotoxic at physiological concentrations. |
| ln Vivo |
H-DL-His-OH is not a pharmacologically active drug and does not have defined in vivo activity as a therapeutic agent. When administered to animals, L-histidine is absorbed and utilized in protein synthesis or decarboxylated to histamine, while D-histidine is metabolized by D-amino acid oxidase. The compound may be used in nutritional studies to investigate histidine metabolism or to assess the effects of histidine supplementation on histamine levels and immune responses. However, the racemic mixture is not used clinically, as L-histidine is the natural form with biological activity. The compound's primary value is in research, where it serves as a tool to study stereospecificity and amino acid physiology.
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| Enzyme Assay |
In vitro enzyme assays using H-DL-His-OH typically involve measuring the activity of histidine-metabolizing enzymes. A standard protocol for histidine decarboxylase involves incubating the substrate with the enzyme preparation (e.g., bacterial or mammalian histidine decarboxylase) in a suitable buffer at pH 7.0-7.5 and 37°C. The production of histamine is quantified using fluorometric, colorimetric, or chromatographic methods. For histidine ammonia-lyase, the production of urocanic acid can be measured by absorbance at 277 nm. The initial velocity is calculated, and kinetic parameters can be determined using various substrate concentrations. These assays are used to study enzyme kinetics, inhibition, and the stereospecificity of the enzymes toward D- and L-histidine.
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| Cell Assay |
In vitro cellular assays using H-DL-His-OH are conducted to study histidine transport and metabolism in cultured cells. A typical protocol involves incubating cells (e.g., intestinal epithelial cells, neurons, or immune cells) with media containing DL-histidine at varying concentrations. Cellular uptake is measured by LC-MS/MS or by using radiolabeled histidine. The production of histamine or other metabolites can be measured in the culture supernatant. The effects on cellular functions, such as proliferation, cytokine production, or neurotransmitter release, can be assessed. These experiments help to elucidate the roles of histidine in cell physiology and the stereospecificity of histidine transporters and enzymes. The compound is generally used at concentrations ranging from 0.1 to 10 mM.
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| Animal Protocol |
In vivo animal studies with H-DL-His-OH are typically conducted in nutritional or metabolic research. A common protocol involves administering the compound to rodents via oral gavage or intraperitoneal injection at doses ranging from 10 to 500 mg/kg. Blood and tissue samples are collected at various time points to measure histidine, histamine, and other metabolites. The effects on histamine levels, immune function, gastric acid secretion, or neurological parameters may be assessed. DL-Histidine can also be used in studies of histidine metabolism in specific disease models, such as histidinemia or allergy. These studies help to understand the pharmacokinetics and biological effects of histidine and its stereoisomers. However, due to the presence of D-histidine, the results may differ from those obtained with L-histidine alone.
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| ADME/Pharmacokinetics |
As a racemic mixture, the pharmacokinetics of H-DL-His-OH are influenced by the different metabolism of the two enantiomers. L-Histidine is actively absorbed in the intestine, distributed throughout the body, and metabolized to histamine, urocanic acid, or incorporated into proteins. D-Histidine is absorbed less efficiently and is metabolized by D-amino acid oxidase in the liver and kidneys, producing hydrogen peroxide and the corresponding α-keto acid. The half-life of D-histidine is generally shorter due to rapid oxidation. The compound's distribution is dose-dependent, and its clearance is primarily renal for L-histidine and enzymatic for D-histidine. In research settings, DL-histidine is used to study stereospecific pharmacokinetics and metabolism. The compound has a melting point of 280-285°C (dec.) and is soluble in water.
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| Toxicity/Toxicokinetics |
The toxicity of H-DL-His-OH is generally low, as it is a mixture of a natural amino acid and its D-isomer. L-Histidine is essential and has no known toxicity at normal dietary levels. D-Histidine is metabolized by D-amino acid oxidase, and at very high doses, the production of hydrogen peroxide could cause oxidative stress, but this is unlikely at typical research doses. The compound may cause mild irritation to skin, eyes, and mucous membranes. It is not classified as a carcinogen, mutagen, or reproductive toxicant. Standard laboratory safety precautions, including the use of personal protective equipment, are recommended. No significant systemic toxicity is anticipated at doses up to 500 mg/kg in rodents.
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| References | |
| Additional Infomation |
DL-Histidine (H-DL-His-OH, CAS 34404-32-5) is a racemic mixture of histidine used as a research tool. Its chemical formula is C₆H₉N₃O₂ and molecular weight is 155.15. The compound appears as a white to off-white crystalline powder with a purity of ≥98% and a melting point of 280-285°C (dec.). It is soluble in water and dilute acids. DL-Histidine is used in studies of amino acid metabolism, enzyme stereospecificity, and as a building block for peptide synthesis when racemic mixtures are desired. It is not approved for human use and is intended for research purposes only. The compound is typically stored at room temperature in a cool, dry place.
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| Molecular Formula |
C14H20N2O4
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| Molecular Weight |
280.3196
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| Exact Mass |
280.142
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| CAS # |
34404-32-5
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| PubChem CID |
1551330
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| Appearance |
White to off-white solid powder
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| Density |
1.206g/cm3
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| Boiling Point |
499.6±45.0 °C at 760 mmHg
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| Melting Point |
229℃
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| Flash Point |
255.9±28.7 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.55
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| LogP |
1.36
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
20
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| Complexity |
304
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC=C(C=C1)COC(=O)NCCCC[C@H](C(=O)O)N
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| InChi Key |
CKGCFBNYQJDIGS-GFCCVEGCSA-N
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| InChi Code |
InChI=1S/C14H20N2O4/c15-12(13(17)18)8-4-5-9-16-14(19)20-10-11-6-2-1-3-7-11/h1-3,6-7,12H,4-5,8-10,15H2,(H,16,19)(H,17,18)/t12-/m1/s1
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| Chemical Name |
(2R)-2-amino-6-(phenylmethoxycarbonylamino)hexanoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5674 mL | 17.8368 mL | 35.6735 mL | |
| 5 mM | 0.7135 mL | 3.5674 mL | 7.1347 mL | |
| 10 mM | 0.3567 mL | 1.7837 mL | 3.5674 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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