Histidinol - ≥97% , CAS No.501-28-0

CAS: 501-28-0 Cat. No.: H1071290 Formula: C6H11N3O PubChem CID: 776

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥97%

Nomi e identificatori

Sorrisi canonici

C1=C(NC=N1)CC(CO)N

IUPAC Name

2-amino-3-(1H-imidazol-5-yl)propan-1-ol

InChIKey

ZQISRDCJNBUVMM-UHFFFAOYSA-N

INCHI

1S/C6H11N3O/c7-5(3-10)1-6-2-8-4-9-6/h2,4-5,10H,1,3,7H2,(H,8,9)

Isomeri SMILES

C1=C(NC=N1)CC(CO)N

PubChem CID

776

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Classe Organonitrogen compounds
      • Subclass Amines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Classe: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Not available
• Direct Parent: Aralkylamines
• Alternative Parents: Imidazoles Heteroaromatic compounds 1,2-aminoalcohols Azacyclic compounds Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Aralkylamine - Azole - Imidazole - Heteroaromatic compound - 1,2-aminoalcohol - Azacycle - Organoheterocyclic compound - Organic oxygen compound - Primary amine - Primary alcohol - Organooxygen compound - Primary aliphatic amine - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 141.170 g/mol
• XLogP3: -1.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 141.09 Da
• Monoisotopic Mass: 141.09 Da
• Topological Polar Surface Area: 74.900 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 99.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No manufacturer protocols are provided for this SKU. The following general research protocols are literature-based suggestions; adjust to your system.

• Enzyme assay (histidinol dehydrogenase, general)

  • Prepare histidinol stock: dissolve in assay buffer (e.g., 50 mM Tris or phosphate, pH 8.0) to 10–100 mM; filter sterilize if needed.
  • Reaction mix: buffer, NAD+ (0.2–1 mM), histidinol (0.1–10 mM), Mg2+ if required, and enzyme source. Incubate at 25–37°C.
  • Readout: monitor NADH formation at 340 nm or quantify histidine by derivatization/LC.

• Microbial selection (conceptual outline)

  • Use only with strains bearing appropriate histidinol resistance/marker genes. Prepare plates or media supplemented with histidinol at literature-recommended concentrations for the specific marker system. Validate minimal inhibitory concentrations for the host background.

• Derivatization for analytical detection

  • For fluorescence or UV enhancement, derivatize the amino group (e.g., with FDAA/Marfey’s reagent) and analyze by RP‑HPLC using volatile buffers.

Note: Concentrations, temperature, and timing must be optimized per enzyme/strain. Always consult primary literature and institutional biosafety guidelines.

Biological Roles

• Literature/general biological context (no clinical claims)

  • Metabolic intermediate: Histidinol is the immediate precursor to L‑histidine in the histidine biosynthetic pathway across bacteria, fungi, and plants. It is produced from histidinal and oxidized by histidinol dehydrogenase (HisD) to histidine, with NAD+ as cofactor.
  • Enzyme studies: Frequently used as a defined substrate for HisD activity assays and to probe regulation of the his operon and related feedback mechanisms in microbes.
  • Transport and uptake: Polar cationic at physiological pH; uptake in microbes may involve amino acid/polyamine transporters (species-dependent, literature reports vary).
  • Metal coordination: The imidazole moiety can coordinate transition metals; histidinol can act as a simple chelating ligand in model studies of metalloenzyme active sites (non-physiological but mechanistically informative).
  • pH-dependent speciation: At neutral pH, protonation of the α‑amine and partial protonation of the imidazole influence binding to proteins, nucleic acids, and membranes, affecting assay design and interpretation.

• Research utilities

  • Selection reagent in engineered strains carrying histidinol dehydrogenase variants or resistance markers (organism- and vector-specific).
  • Building block for synthesizing histidine analogs and probes to interrogate histidine-dependent catalysis and binding.

Note: All uses are for research and laboratory investigations only.

Buffer Applications

• Applicability: Histidinol itself is not a standard laboratory buffer component. While its imidazole ring exhibits acid–base activity, dedicated buffers such as histidine, imidazole, phosphate, Tris, and HEPES are preferred for defined buffering capacity.

• Practical guidance

  • If buffering near pH ~6–7 is required, consider histidine or imidazole buffers (literature pKa values ~6.0–6.8 for the imidazolium), which provide predictable buffer capacity and established recipes.
  • Histidinol solutions can alter pH due to amine protonation, but should not be relied upon for buffering; use an appropriate buffer system and treat histidinol as a solute.

• References for alternatives (general)

  • Histidine buffer: useful ~pH 5.5–7.0
  • Imidazole buffer: useful ~pH 6.2–7.5
  • Phosphate buffer: useful ~pH 6.0–8.0

Conclusion: Use a proper buffer; include histidinol as a component only if required by the assay, and verify pH independently.

Green Alternatives

• Context: Histidinol is a solid building block/biochemical, not a process solvent. “Greener” considerations focus on solvent choice and protecting-group strategy during its use rather than replacing the molecule itself.

• Greener solvent choices (literature/general)

  • Prefer water or aqueous ethanol for dissolution in bioassays when compatible with the system.
  • For organic reactions, consider bio-derived solvents such as 2‑MeTHF or Cyrene in place of chlorinated solvents; use EtOAc over DMF/DMAc when feasible.
  • For extractions/purifications, employ aqueous biphasic systems or ethanol/EtOAc, and minimize use of halogenated solvents.

• Example comparison (general)

  • Traditional: DMF, DCM for acylations and couplings; MeCN for LC.
  • Greener alternative: 2‑MeTHF or EtOAc for acylations; water/EtOH for couplings using water-tolerant reagents; ethanol/water mobile phases for prep RP chromatography.

• Waste minimization

  • Use protecting-group strategies that allow telescoped steps and avoid hazardous deprotection reagents (e.g., enzymatic catalysis, carbonate‑based protections).
  • Favor catalytic oxidations (e.g., TEMPO/bleach in water, transfer hydrogenation) over stoichiometric chromium or Dess–Martin reagents when oxidizing the alcohol.

Note: Validate reaction performance when changing solvents; physical properties (solubility, rates) can differ substantially.

Pharmaceutical Uses

• Applicability: Histidinol is primarily a research biochemical and synthetic building block. No pharmacopeial monograph or excipient designation is indicated here.

• Formulation/contextual notes (general)

  • As a polyfunctional amino alcohol, histidinol forms stable salts with mineral and organic acids; salt formation can modulate solubility for in vitro studies.
  • The imidazole ring introduces UV absorbance that can be leveraged for analytical monitoring in formulation studies (e.g., stability indicating methods), though this product is not presented as a pharmaceutical ingredient.
  • In preformulation research, amino alcohols are sometimes explored as counterions or complexing agents; any such use should remain within non-clinical laboratory investigations.

• Compliance

  • This product is supplied for research use only. It is not intended for use in humans, animals, or diagnostic applications. Confirm all regulatory requirements before considering any development-related studies.

Physical Properties

• Item-specific values

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula, molecular weight, SMILES, InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/typical properties (reference only; not item-specific specifications)

  • Physical state: typically a solid or viscous solid depending on salt form and hydration; free base is hygroscopic in many reports.
  • Solubility: highly soluble in water due to ionizable amine and polar imidazole; soluble in lower alcohols; poorly soluble in nonpolar solvents.
  • Acid–base behavior: amphoteric. Imidazole ring pKa of conjugate acid typically ~6.0–7.0; primary amine pKa typically ~9–10 (literature ranges depend on ionic strength and temperature). Alcohol is non-ionizing under neutral conditions.
  • Partitioning: expected low logP and high logD dependence on pH due to protonation state (literature generalization for amino alcohols with imidazole).
  • Hygroscopicity: amino alcohols with heteroaromatics may absorb moisture/CO2 (literature observation); handle quickly in ambient humidity.

Notes: For exact melting point, water content, residual solvents, metal content, and other release specifications, consult the item’s CoA/Spec Sheet. Do not treat literature values as specifications.

Quality and Grades

• Item-specific quality information

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grades (general guidance)

  • Research/Biochemical grade: Typically emphasizes low bioburden and suitability for biochemical assays; may include tighter controls on inorganic ions and UV-absorbing impurities that could interfere with enzyme assays (consult CoA for this item).
  • Synthetic/Technical grade: Suitable for general organic synthesis; may have broader impurity profiles not suitable for sensitive bioassays.
  • Salt forms: Histidinol is frequently supplied as free base or as mineral acid salts (e.g., dihydrochloride) in the literature; verify the exact form on the CoA, as mass, solubility, and handling differ.

• Practical notes for this compound class

  • UV background: Imidazole chromophore absorbs in the UV region; for chromatographic applications, confirm “low UV” specifications if needed.
  • Moisture content: Amino alcohols may be hygroscopic; Karl Fischer water and residual solvent content, if critical, should be verified on the CoA.

Conclusion: Consult the specific CoA/Spec Sheet accompanying this SKU for definitive assay, purity profile, counterion (if any), and analytical limits. Do not infer specifications from literature.

Reaction and Applications

• Research and assay applications (literature/general)

  • Biochemical substrate: Histidinol is the direct substrate of histidinol dehydrogenase (HisD), converting histidinol to histidine in the terminal steps of histidine biosynthesis (bacteria, fungi, plants). Employed in enzyme kinetics and pathway studies.
  • Genetic/selection marker systems: Histidinol resistance or utilization phenotypes are used in microbial genetics; histidinol can serve as a selective agent in certain yeast and bacterial systems when paired with appropriate marker genes (consult strain/construct documentation).

• Synthetic/chemical applications (literature)

  • Bifunctional building block: The primary amine and alcohol enable orthogonal transformations (e.g., N‑acylation, O‑acylation, Mitsunobu conversion of the alcohol, carbamate/urethane formation).
  • Imidazole chemistry: The ring can be N‑alkylated, metal-coordinated, or used to construct imidazolium salts and ligands for catalysis.
  • Oxidation/state manipulation: Oxidation of the primary alcohol provides the corresponding aldehyde or acid; with stereocontrol preserved, this relates to histidine derivatives when the carboxylate is regenerated via oxidation (route-dependent).

• Practical tips (general)

  • Protecting groups: Consider Boc/CBz/Fmoc on the amine and TBDMS/benzyl carbonate on the alcohol to enable selective transformations; imidazole N can be protected (e.g., trityl) if needed.
  • Protonation control: Reaction outcomes can depend on protonation (amine vs imidazole); adjust pH/base to favor desired nucleophilicity.
  • Purification: Strong polarity favors reversed-phase chromatography or ion-exchange; for salts, lyophilization from aqueous media is common.

Reaction Conditions

General guidance below is based on literature precedent for amino alcohols and imidazole-containing substrates; optimize per your system. These are not item-specific specifications.

• Protection/derivatization

  • N‑Boc protection: Boc2O (1.1–1.5 equiv), base (Na2CO3 or DIPEA), solvent H2O/dioxane or MeCN, 0–25°C, 1–4 h. Monitor by LC-MS.
  • O‑silylation: TBDMS‑Cl (1.2 equiv), imidazole (2–3 equiv), DMF or MeCN, 0–25°C, 2–12 h.
  • Imidazole N‑protection: Trityl chloride (1.1–1.5 equiv), base (Et3N), DCM, 0–25°C; or benzylation under mild conditions.

• Alcohol oxidation

  • TEMPO/NaOCl: CH2Cl2/H2O buffer (pH ~9), 0–5°C to rt, 0.5–2 h to aldehyde; longer or NaClO2 step for acid. Alternatively, catalytic TEMPO/bleach in water/MeCN as a greener option.
  • Swern/DMP/PCC: 0 to rt, 1–3 h (avoid overoxidation; protect amine when needed).

• Mitsunobu substitution (O→N inversion/replacement)

  • DEAD/DIAD with PPh3 in THF or toluene at 0–25°C; use appropriate nucleophile (e.g., phthalimide, benzoate). Consider greener variants (e.g., polymer-supported reagents).

• N‑Acylation/Amide formation

  • Activated esters (NHS, Pfp) or carbodiimide coupling (EDC/HOBt, DIC/DMAP) in water-miscible solvents (DMF, MeCN, 2‑MeTHF); 0–25°C, 1–16 h. Control pH to 7.5–9 for selectivity.

• Purification/analytics

  • HILIC or RP‑HPLC with aqueous ammonium formate/acetate (pH 4–6) for LC-MS compatibility. Ion-exchange for salts. Lyophilization commonly used to isolate salts from water.

Safety and Handling

• Item-specific hazard information (from Product Data)

  • Signal word: Not specified for this item; refer to SDS.
  • H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.

• General laboratory safety guidance (literature/general)

  • Likely hazards: Amino alcohols and heteroaromatics can cause irritation to skin, eyes, and respiratory tract. Avoid dust/aerosol formation.
  • PPE: Wear lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure.
  • First aid overview: If inhaled—move to fresh air; seek medical attention if symptoms persist. Skin/eye contact—rinse with water for at least 15 minutes; remove contaminated clothing. If ingested—rinse mouth; do not induce vomiting; seek medical attention. Always defer to the SDS.
  • Incompatibilities: Strong oxidizers; acylating and alkylating agents (reactive toward nucleophilic amine/alcohol). May form salts with strong acids; avoid uncontrolled neutralization/acid–base reactions with heat evolution.
  • Spill/cleanup: Avoid raising dust; collect solids by gentle sweeping or HEPA vacuum; wash area with water/compatible solvent while wearing PPE.
  • Waste: Dispose according to institutional and local regulations for organic nitrogen-containing compounds.

Always consult the product SDS for authoritative hazard classification and response procedures.

Solvent Selection

• Polarity and ionization (general/literature)

  • Histidinol is a polyfunctional, basic compound with an imidazole side chain. It is highly polar in its protonated forms and exhibits strong hydrogen-bonding capability.

• Solubility profile (literature expectations)

  • Water: high solubility, especially under acidic conditions where the amine/imidazole are protonated.
  • Alcohols (MeOH, EtOH): generally soluble; solubility may increase with slight acidification.
  • Polar aprotics (DMSO, DMF): highly soluble; useful for stock solutions for biochemical assays.
  • Nonpolar solvents (hexanes, toluene, MTBE): poor solubility.

• Selection tips

  • Aqueous work: Choose buffered aqueous media at pH 5–8 to maintain solubility while preserving imidazole functionality.
  • Organic synthesis: Use mixed solvent systems (e.g., MeOH/CH2Cl2, MeOH/THF) or polar aprotics for acylations/alkylations; add base or acid as needed to control protonation.
  • Chromatography: Normal-phase is challenging due to strong polarity; reversed-phase or HILIC is preferred. Include volatile buffers (e.g., ammonium formate/acetate) for LC-MS.

• Brief comparison (literature)

  • Water vs DMSO: Water is preferred for bioassays; DMSO offers higher stock concentrations and compatibility with organic transformations but may affect enzymes. Balance assay tolerance with solubility needs.

Storage and Reconstitution

• Item-specific storage

  • Storage conditions: Room temperature (per Product Data).
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• General handling and stability (literature/general)

  • Store in a tightly closed container, protected from moisture. For hygroscopic amino alcohols, a desiccator is recommended.
  • If long-term storage is anticipated, consider refrigeration (2–8°C) as a precaution, especially for aqueous solutions; avoid repeated freeze–thaw of solutions.

• Reconstitution guidance (general)

  • Solvents: Water, buffer (adjust pH 5.5–8.0), or polar organics (DMSO) depending on application.
  • Typical stock solutions: 10–500 mM in water or DMSO for lab use; filter-sterilize (0.22 μm) for biological assays.
  • pH considerations: Protonation enhances solubility; mild acidification (e.g., dilute HCl) may aid dissolution for the free base. Avoid strong acids/bases if not required by protocol.

• Stability of solutions (general)

  • Aqueous stocks are generally stable for days to weeks at 2–8°C; prepare fresh as needed for sensitive assays.

Always consult the product’s CoA/SDS for specific guidance on stability, container compatibility, and transport conditions.

Structure and Identity

Brief overview: Histidinol is the amino‑alcohol corresponding to the carboxyl‑reduced form of histidine; it bears an imidazole side chain, a primary alcohol (–CH2OH), and a primary amino group on the α‑carbon.

• Item-specific (from Product Data)

  • Product name: Histidinol (SKU H1071290)
  • CAS: 501-28-0
  • Storage conditions: Room temperature
  • Research use: For research use only
  • Other identifiers (SMILES, InChIKey, MF, MW): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/typical identity data (for reference only; not item-specific specs)

  • Common molecular formula: C6H11N3O
  • Typical molecular weight: ~141.17 g/mol
  • Core functional groups: primary alcohol (–CH2OH), primary amine (–CH–NH2), imidazole ring (1H‑imidazol‑4‑yl substituent)
  • 2D structural description: an imidazole ring attached via a methylene (–CH2–) to the α‑carbon, which also bears an amino group and a hydroxymethyl substituent; stereochemistry may be undefined unless specified (DL mixture) or specified as L- or D-histidinol.

• Structural features of note

  • Bifunctional nucleophile (amine and alcohol)
  • Heteroaromatic imidazole capable of metal coordination and acid–base chemistry
  • Potential chirality at the α‑carbon (not defined in this listing)

Synthetic Utility

• Functional group leverage (literature/general)

  • Primary amine: amenable to acylation (amides, ureas), carbamate formation (Boc, Cbz, Fmoc protection), reductive amination, and metal-catalyzed coupling after activation.
  • Primary alcohol: enables esterification, carbamate/urethane formation, Mitsunobu substitution to invert/replace OH, and oxidation to aldehyde/acid for accessing histidine analogs.
  • Imidazole: undergoes N‑alkylation/acylation, quaternization to imidazolium salts, and serves as a ligand/anchoring group in organometallic and materials chemistry.

• Retrosynthetic value

  • As a carboxyl-reduced histidine surrogate, histidinol allows stepwise reconstruction of the carboxylate or diversification of the side chain prior to oxidation, aiding access to noncanonical histidine derivatives.
  • Orthogonal protection: selective protection of amine vs alcohol vs imidazole enables convergent syntheses of multifunctional targets, peptidomimetics, and chelating ligands.

• Representative transformations (literature)

  • Selective N‑acylation in aqueous/green media using activated esters or enzymatic acylation.
  • Oxazoline/oxazolidinone formation from amino alcohol under dehydrative cyclization, providing chiral auxiliaries or intermediates.
  • Metal-binding ligand synthesis via imidazole N‑functionalization followed by immobilization on polymers or silica for affinity media.

Target Specificity

This product is a small-molecule biochemical, not an antibody or affinity reagent.

• Item-specific data required for target specificity (antigen, clone, isotype, species reactivity): Not applicable to this product type.

• Research context (general)

  • In biochemical assays, histidinol serves as a substrate for histidinol dehydrogenase (HisD). Any “specificity” arises from the enzyme–substrate relationship within the histidine biosynthetic pathway rather than from immunological binding parameters.