Emixustat - ≥99% , CAS No.1141777-14-1

CAS: 1141777-14-1 Cat. No.: E731519 Formule: C₁₆H₂₅NO₂ Poids moléculaire: 263.37 PubChem CID: 25221720

GRADE & PURITY ≥99%

Storage

Room temperature

Specifications

Spécifications et pureté

≥99%

Conditions de stockage de stockage

Room temperature

Type d'action

INHIBITOR

Pureté

≥99%

Propriétés du produit

ALogP

2.8

Noms et identifiants

Sourires canoniques

C1CCC(CC1)COC2=CC=CC(=C2)C(CCN)O

IUPAC Name

(1R)-3-amino-1-[3-(cyclohexylmethoxy)phenyl]propan-1-ol

InChIKey

WJIGGYYSZBWCGC-MRXNPFEDSA-N

INCHI

1S/C16H25NO2/c17-10-9-16(18)14-7-4-8-15(11-14)19-12-13-5-2-1-3-6-13/h4,7-8,11,13,16,18H,1-3,5-6,9-10,12,17H2/t16-/m1/s1

Isomères SMILES

C1CCC(CC1)COC2=CC=CC(=C2)[C@@H](CCN)O

CAS alternatif

1141777-14-1

PubChem CID

25221720

Termes d'entrée MeSH

ACU-4429;emixustat

Poids moléculaire

263.37

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Phenoxy compounds Aralkylamines Alkyl aryl ethers 1,3-aminoalcohols Secondary alcohols Monoalkylamines Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Phenol ether - Alkyl aryl ether - Aralkylamine - Monocyclic benzene moiety - 1,3-aminoalcohol - Secondary alcohol - Ether - Organic nitrogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Aromatic alcohol - Hydrocarbon derivative - Amine - Organic oxygen compound - Alcohol - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
• 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

Propriétés chimiques et physiques

• Poids moléculaire: 263.370 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 263.189 Da
• Monoisotopic Mass: 263.189 Da
• Topological Polar Surface Area: 55.500 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 241.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• 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

• Item-specific tested applications and protocols: Not specified for this item.

• General research usage notes (non-validated; adapt to your system)

  • Stock preparation: Dissolve in anhydrous DMSO to 10–50 mM. Store aliquots at ≤−20 °C, protected from light. Thaw immediately before use and avoid repeated freeze–thaw.
  • Biochemical assays: Dilute DMSO stock into assay buffer to a final DMSO concentration ≤1% v/v. Include vehicle controls. Verify solubility and absence of aggregation (e.g., by light scattering or detergent controls).
  • LC–MS quantification: Prepare calibration curves in matrix-matched solutions. Use stable-isotope-labeled internal standards if available. Assess carryover and stability in autosampler.

• Disclaimer

  • The above are general good-practice guidelines and are not item-specific validated protocols. Consult the literature and perform pilot experiments to qualify conditions for your assay.

Biological Roles

• Context (literature; no clinical claims)

  • Emixustat is described in the literature as a small-molecule modulator of the visual (retinoid) cycle in retinal pigment epithelium. It is reported to interact with the enzymatic pathway responsible for the isomerization of all-trans-retinyl esters to 11-cis-retinol, thereby attenuating chromophore regeneration in photoreceptors (literature). These properties make it useful as a research probe for dissecting retinoid metabolism and light-adaptation mechanisms.

• Experimental usage (general research)

  • Tool compound in enzyme assays and cell-free systems modeling steps of the visual cycle.
  • Reference material in analytical workflows quantifying retinoids and related metabolites by LC–MS/MS.
  • Aid for studying phototransduction adaptation by modulating chromophore availability in ex vivo models.

• Practical considerations

  • Light sensitivity: When working alongside retinoids, control light exposure rigorously to avoid confounding degradation.
  • Protein/serum binding: Basic, hydrophobic small molecules can show significant nonspecific binding; consider adding inert carriers (e.g., low levels of Tween-20 or BSA) for consistent assay recovery, if compatible with your system.

• Note

  • Target specificity and potency parameters are not provided for this item; consult primary literature and verify under your assay conditions.

Buffer Applications

• Not a buffering agent. Emixustat is a small organic research compound and does not serve as a pH buffer.
• Practical note (general)
  • If preparing aqueous solutions of amine-containing small molecules, acetate or citrate buffers at pH 3–5 are commonly used to enhance solubility of protonated species (literature). Verify compatibility with your assay readout.

Green Alternatives

• Scope

  • As a solid small molecule used mainly as a research reference or probe, “green alternatives” pertain to solvent choices and handling practices rather than replacement of the compound itself.

• Greener solvent considerations (general)

  • Prefer water or buffered aqueous media for salt forms when feasible.
  • Ethanol over methanol, and acetonitrile over DMF for certain analytical methods, where solubility and stability permit.
  • Minimize DMSO volumes in biological assays to ≤0.1–1% v/v to reduce solvent burden.

• Comparison (general guidance; not item-specific specifications)

  | Use case | Typical choice | Greener alternative | Trade-offs | |---|---|---|---| | Stock solution for screening | DMSO | 50% EtOH/water or acetate buffer (pH 4–5) for salt forms | Possible lower solubility; stability must be verified | | LC–MS sample | MeOH or ACN | EtOH (if method compatible) | Viscosity/ionization efficiency may vary | | Crystallization/recovery | ACN/EtOAc | EtOAc/IPA mixtures | Solubility may limit yield |

• Process choices

  • Use amber vials, minimize energy-intensive freeze–thaw by aliquoting, and adopt microscale assays to reduce chemical consumption.

Pharmaceutical Uses

• Scope

  • No therapeutic or clinical claims are made. For research use only.

• Research/formulation context (general)

  • Emixustat may be used as a reference standard for analytical method development (e.g., dissolution, stability-indicating HPLC) in preformulation research.
  • Salt-form screening, polymorph assessment, and hygroscopicity testing can be conducted to understand solid-state behavior in a research/manufacturing development setting.
  • Compatibility studies with common excipients (e.g., microcrystalline cellulose, lactose, HPMC) may be performed in early-stage formulation research; none are specified for this item.

• Standards and compliance

  • No pharmacopeial monograph is referenced for this item. Where compendial alignment is needed, develop in-house specifications mirroring typical compendial quality attributes (identity, purity, assay, residual solvents, water, heavy metals) and document on a study-specific specification sheet.

Physical Properties

• Item-specific physical properties (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties (context; not item specifications)

  • Emixustat and its salts are typically solids at ambient temperature (literature). Solubility is commonly enhanced in polar aprotic solvents (DMSO, DMF) and in dilute aqueous acid when a protonated amine is present (literature).
  • Ionization: contains at least one basic amine; expected to be cationic under acidic conditions, improving aqueous solubility (literature).
  • Partitioning: as a small organic base, logP/logD can vary substantially with pH and salt form; determine experimentally for your system.

• Methodological guidance

  • For quantitative work, measure solubility and logD at experimental pH and ionic strength.
  • Confirm melting point and water content by DSC/TGA/KF on the received lot if these attributes are critical for your application.
  • Any specific values required for method validation should be derived from the lot-specific CoA and verified in-house.

Quality and Grades

• Item-specific information

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

• Guidance on interpreting grades (general)

  • Research grade materials are typically suitable for method development, screening, and exploratory studies. If LC–MS reference-standard quality is required (e.g., quantitative bioanalysis), verify assay, residual solvents, and inorganic content by CoA and, if necessary, perform in-house qualification.
  • For materials used in trace analysis, low UV background and low nonvolatile residue are advantageous; confirm if an HPLC/LC–MS grade statement is provided on the lot CoA.

• Practical quality controls

  • Identity confirmation: NMR, HRMS, and HPLC/UPLC purity check under your analytical method.
  • Moisture and form: Karl Fischer and chloride assay (if salt form is claimed) to confirm stoichiometry.
  • Stability-indicating methods: Develop a short UPLC method to monitor forced-degradation pathways (acid/base, oxidative, thermal, photolytic) for your workflow.

• Note

  • Where specific numeric specifications (e.g., purity %, water content) are required, rely on the lot-specific CoA; values are Not specified for this item in the current listing.

Reaction and Applications

• This product is primarily a small-molecule research chemical rather than a general-purpose reagent.

• Applications (research use; literature/general)

  • Employed as a reference/benchmark compound in biochemical studies interrogating the visual cycle in retinal pigment epithelium models (e.g., enzyme assays). No medical or clinical claims are made; for research use only.
  • Utilized in analytical method development (HPLC/UPLC, LC–MS/MS) as a system suitability or calibration reference in laboratories studying retinoid pathway biochemistry.

• Practical tips

  • Prepare concentrated DMSO stocks to reduce freeze–thaw cycles; dispense single-use aliquots.
  • Verify salt form and neutral equivalent before preparing molar solutions.
  • For photolabile systems, protect from strong light during assays and sample prep.

• Not typically used in synthetic transformations

  • Unlike building blocks or catalysts, emixustat is not commonly employed as a reagent in bond-forming reactions. If derivatization is desired (e.g., to create internal standards), standard amine-functional compound handling applies (literature).

Reaction Conditions

• Not generally applicable

  • This compound is not typically employed as a reagent or catalyst in synthetic reactions; therefore, standard “reaction condition” guidance is not applicable.

• If derivatization is undertaken (general guidance)

  • Solvents: DMF, DCM, MeCN, or THF for acylation/alkylation of amines; ensure anhydrous conditions when required.
  • Bases: DIPEA, triethylamine, or Na2CO3 for acylations/carbamate formations.
  • Temperatures: 0–25 °C for most functionalizations to maintain integrity; monitor by TLC/UPLC.
  • Workup: Aqueous quench with pH control to avoid amine protonation complications; extract with appropriate organic solvent; protect from strong light if relevant.

• Note

  • All parameters above are general, literature-style guidance for amine-containing small molecules and are not item-specific specifications.

Safety and Handling

• Product Data safety fields

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification/Pictograms: Not specified for this item; refer to SDS.

• General laboratory precautions (not a substitute for SDS)

  • Handle in a fume hood; avoid inhalation of dust or aerosols. Use appropriate PPE: lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile).
  • Avoid contact with strong oxidizers and strong acids/bases until compatibility is established for the specific form (free base vs. salt).
  • If preparing DMSO or DMF stocks, prevent skin contact; these solvents facilitate dermal absorption of solutes.

• First-aid overview (general)

  • Skin/eye contact: Rinse with water for ≥15 min. Remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: Move to fresh air. Seek medical advice if symptoms develop.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.

• Hygiene and waste

  • Avoid release to the environment; dispose of contents/containers in accordance with institutional and regulatory requirements.
  • Defer to the product-specific SDS for authoritative hazard, toxicological, and exposure-control information.

Solvent Selection

• Item-specific solubility: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general dissolution guidance for small organic bases like emixustat

  • Primary/secondary amines often dissolve well in polar aprotic solvents such as DMSO and DMF; moderate solubility may be achieved in acetonitrile, methanol, or ethanol (literature). Protonated forms (e.g., hydrochloride salt) dissolve more readily in aqueous media at low pH.
  • Suggested stock preparations (general practice)
    • DMSO stocks: 10–50 mM are commonly used for bioassays; further dilute into assay buffers with ≤1% final DMSO to minimize solvent effects.
    • Acidified aqueous: For salt forms, dissolve in water or buffer adjusted to pH 3–5; filter sterilize if needed for cell-free biochemical assays.

• Selection tips

  • For LC–MS reference solutions: use LC–MS grade DMSO/MeOH and syringe filtration (0.2 µm PTFE) to remove particulates.
  • For stability: minimize exposure to light and elevated temperature; consider amber vials and inert headspace if long-term storage of solutions is required.

• Comparison (general)

  • DMSO: maximal solubilization, excellent for small-molecule stocks; high boiling point.
  • MeOH/EtOH: good miscibility with water; may reduce stability for some amines.
  • Buffer (pH < pKa of amine): enhances aqueous solubility for protonated species.

Storage and Reconstitution

• Item-specific storage/shipping

  • Storage Conditions: Room temperature (as provided in Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance (supplemental; not item-specific specifications)

  • Keep container tightly closed, in a dry place, protected from strong light. Use desiccant if hygroscopicity is observed.
  • For long-term stability of solutions, prepare single-use aliquots and store frozen (e.g., −20 to −80 °C) in amber vials to minimize light- and temperature-induced degradation.

• Reconstitution (general practice)

  • Choose solvent based on assay: DMSO for maximum solubility; aqueous acidic buffer for salt forms if compatible. Filter through 0.2 µm PTFE/nylon if particulate is present.
  • Record exact solvent, concentration, and lot number on vial labels and in ELN/LIMS for traceability.

• Note

  • Where exact shelf life, permissible freeze–thaw cycles, and solution stability are required, these are Not specified for this item; determine empirically and consult the lot-specific CoA/SDS.

Structure and Identity

• Item-specific identifiers (from Product Data)

  • SKU: E731519
  • Product Name: Emixustat
  • CAS: 1141777-14-1
  • InChIKey: 399937 (as provided; note this does not match the typical InChIKey format — verify on CoA/SDS)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general identity notes (for context; not item specifications)

  • Emixustat is known in the literature as a small-molecule modulator of the visual cycle and is often handled either as the free base or as the hydrochloride salt (literature).
  • Structural features (literature): non-retinoid scaffold bearing a basic amine functionality; typically formulated as a salt for improved handling. Exact 2D structure and stereochemistry should be confirmed from primary literature or reference standards.

• Practical identity guidance

  • Because the salt form and exact structural identifiers are not specified in this listing, confirm the form (free base vs. salt) and stereochemistry from the product’s CoA before quantitative work (e.g., assay prep, LC–MS reference standard preparation).

Synthetic Utility

• Not a general-purpose building block

  • Emixustat is typically used as a finished small-molecule probe/reference rather than a synthon.

• Derivatization possibilities (general chemistry)

  • If the molecule bears a primary/secondary amine (literature indicates a basic amine functionality), potential transformations include: acylation to amides, carbamate formation, reductive alkylation, N-alkylation under controlled conditions, and isotopic labeling for internal standards.
  • For analytical internal standards, introduce stable isotopes (2H, 13C, 15N) at metabolically stable positions; verify that derivatization does not alter chromatographic behavior beyond intended scope.

• Cautions

  • Any modification will change physicochemical and biological properties; do not extrapolate activity from the parent compound without empirical verification.
  • Protect potential photolabile motifs during synthesis and workup if working alongside retinoid system probes.

Target Specificity

• Item-specific target information: Not specified for this item; refer to CoA/Spec Sheet and primary literature.
• General note
  • While emixustat is discussed in literature within the context of the visual cycle, no target, potency, or selectivity data are provided in this product listing. Users should verify biochemical targets and assay conditions independently.