GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.10 mM in DMSO
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Punto di fusione (°C)
86 °C
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Recensioni
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Application Protocols
No vendor‑validated bioassay protocols are provided for this item. The following are general research workflows (literature/practice) suitable for α‑hydroxy fatty acids:
DMSO stock preparation for screening:
Warm the vial to room temperature in a desiccated environment. Add anhydrous DMSO to achieve 10–50 mM. Vortex and sonicate gently until fully dissolved. Filter (PTFE, 0.2 µm) if particulates persist. Aliquot and store at −80 °C to avoid freeze–thaw.
Liposome incorporation (thin‑film hydration):
Dissolve 2‑hydroxypalmitic acid with other lipids (e.g., phosphatidylcholine, cholesterol) in CHCl3/MeOH (2:1). Evaporate to a thin film under reduced pressure. Dry ≥2 h under high vacuum. Hydrate with warm buffer (e.g., PBS, 40–60 °C) to desired concentration with vigorous vortexing. Optional: Extrude through 100–200 nm membranes. Characterize by DLS and lipid assay.
Esterification to analytical standards (methyl ester):
Reflux in methanolic HCl (3N) 1–3 h under N2. Quench with saturated NaHCO3, extract with hexanes/Et2O, wash, dry, and concentrate. Analyze by GC–MS.
These are general guidelines; optimize solvent, temperature, and ratios for your system. Item-specific tested applications, recommended dilutions, and positive controls are not specified for this item.
Biological Roles
General biochemical context (literature; not a medical claim):
2‑Hydroxypalmitic acid is a member of the 2‑hydroxy fatty acids that occur naturally as N‑acyl chains in sphingolipids (e.g., 2‑hydroxy‑ceramides and galactosylceramides). Its biosynthesis in mammals is catalyzed by fatty acid 2‑hydroxylase (FA2H), which introduces the α‑hydroxy group into saturated acyl chains prior to sphingolipid assembly.
The α‑hydroxy substitution modulates lipid packing, hydrogen bonding, and membrane phase behavior. In myelin and other highly ordered membranes, 2‑hydroxy acyl chains contribute to stability and protein–lipid interactions.
Degradation involves peroxisomal α‑oxidation pathways; the α‑OH enables decarboxylative steps not accessible to non‑hydroxylated fatty acids. Metabolic interconversion with 2‑keto fatty acids can occur via dehydrogenases.
Research utility:
Tool compound for reconstituting 2‑hydroxy‑sphingolipids in model membranes or proteoliposomes to study membrane order, raft formation, and lipid–protein affinity.
Standard for analytical lipidomics (monitoring FA2H activity, profiling 2‑hydroxy acyl pools). Derivatization (e.g., to methyl/benzyl esters) can enhance chromatographic performance.
Item-specific biological certifications, source, stereochemistry, and endotoxin levels are not specified for this item; refer to CoA/Spec Sheet if such parameters are critical to your application.
Buffer Applications
This compound is not a buffering agent and is not typically used to establish or maintain buffer pH.
Practical notes (general):
Aqueous use typically requires conversion to the sodium or potassium salt to improve dispersion at neutral pH. Incorporation into buffers is commonly achieved via co‑solvent (e.g., ≤1–2% DMSO or ethanol) and carriers (fatty acid–free BSA, cyclodextrins, or lipid vesicles).
For liposome or micelle‑based delivery into buffered systems, pre‑formulate in a thin‑film and hydrate with the target buffer (e.g., PBS) at temperatures above the lipid transition to ensure uniform incorporation.
For actual buffer recipes, pKa values, and capacities, refer to dedicated buffering agents (HEPES, Tris, phosphate).
Green Alternatives
Greener choices relate primarily to solvent and reagent selection during derivatization or formulation; the substrate itself is a lipid‑like molecule.
Greener solvent swaps (literature/general):
Replace DCM with ethyl acetate or 2‑MeTHF for extractions and some couplings.
Substitute THF with 2‑MeTHF or CPME in esterifications and protection steps.
Favor ethanol over methanol where feasible (lower toxicity) for Fischer esterifications or stock solutions.
More benign reagents:
Use EDC·HCl (water‑soluble urea byproduct) instead of DCC (allergenic dicyclohexylurea) for Steglich‑type couplings.
Employ catalytic organobases (DMAP, pyridine alternatives) judiciously; recover and reuse where possible.
Waste and energy considerations:
Given its high melting point relative to many solvents, mild warming rather than reflux often suffices for dissolution; employ closed‑loop solvent recovery.
Convert workups to aqueous bicarbonate/acid brine sequences to minimize chlorinated waste.
Alcoholic media | MeOH | EtOH/i‑PrOH | Reaction rate can be slower
Note: No item‑specific environmental certifications are provided; consult your EHS program for process‑level green metrics (E‑factors, PMI).
Pharmaceutical Uses
No therapeutic claims are made. The following refers to formulation and process roles in research and development contexts (literature/general):
Excipient and delivery research:
As a hydrophobic α‑hydroxy fatty acid, 2‑hydroxypalmitic acid can serve as a lipid component in experimental liposomes, solid lipid nanoparticles, or self‑emulsifying drug delivery systems to modulate membrane rigidity and hydrogen‑bonding at the interface.
Ester or amide derivatives may act as pro‑lipophilic conjugates to enhance membrane permeability or depot behavior in preclinical studies.
Processing considerations:
The α‑OH offers additional handles for conjugation (e.g., carbonate/carbamate linkages to APIs or polymers) compared with non‑hydroxylated palmitic acid.
For analytical QC in formulations, derivatization to methyl esters (FAMEs) facilitates GC analysis; HPLC with evaporative or MS detection is used for the intact acid and conjugates.
Regulatory/status notes:
Pharmacopeial monographs, residual solvent limits, and specific excipient specifications are not provided for this item. Any use in manufacturing requires independent qualification, safety assessment, and compliance with applicable regulations.
Item-specific pharmacopeia status, residuals, and impurity profiles: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific properties from Product Data:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage/Shipping (from Product Data):
Storage: Store at −80 °C.
Shipped: On dry ice packs + cold packs.
Literature/general physical data (reference values; not item-specific specifications):
Physical state: Waxy solid or crystalline solid at ambient temperature (typical for long‑chain saturated α‑hydroxy acids).
Melting point: Reported values vary in literature depending on stereochemistry and purity; generally elevated relative to palmitic acid due to α‑OH and potential H‑bonding. Specific value not provided here.
Boiling point: Not meaningful at 1 atm (thermal decomposition before boiling); handled as a high‑melting solid.
Solubility: Practically insoluble in water at neutral pH; soluble in polar organic solvents (e.g., methanol, ethanol), chlorinated solvents, and DMSO; increased aqueous solubility upon conversion to its sodium/potassium salt or at pH > pKa.
Acid dissociation: Carboxyl pKa typically in the ~3.6–4.2 range for α‑hydroxy fatty acids (literature; depends on medium/ionic strength).
Partitioning: High hydrophobicity expected; logP estimated >5 (literature/computational estimates for C16 α‑hydroxy acids).
Numerical values (mp, density, refractive index, water content, metal content) are not specified for this item; refer to CoA/Spec Sheet.
Actual behavior can vary with enantiomeric composition and microstructure (crystalline polymorph vs amorphous).
Quality and Grades
Item-specific grade (from Product Data):
Grade: Moligand™
Interpretation and context (general; not a specification):
Moligand™ indicates inclusion in a small‑molecule/compound library suitable for ligand discovery, biochemical screening, or medicinal chemistry hit‑finding workflows. Such materials are commonly provided with identity confirmation (e.g., NMR/HRMS) and a defined storage and shipping regimen to preserve integrity for screening.
UV cutoffs, residual solvent content, water content, metals, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Practical implications for users:
Expect research‑grade material appropriate for SAR exploration, target‑agnostic screening, or as a reference standard for lipid biochemistry assays. If chromatographic grade (HPLC/LC–MS) performance or enantiomeric purity is required, verify via the CoA and, if needed, perform in‑house QC (e.g., chiral HPLC, Karl Fischer, residual solvent by GC–MS).
Stereochemistry: The Moligand™ listing does not specify (R) vs (S) or racemate for this item. If biological assays are sensitive to configuration (common for 2‑hydroxy fatty acids), confirm enantiomeric composition or resolve as necessary.
Documentation:
For exact acceptance criteria (assay, impurities, residual solvents), please consult the CoA/Spec Sheet provided with the batch.
Reaction and Applications
Representative applications (literature/general; expandable from common use of α‑hydroxy fatty acids):
Lipid biochemistry: Reference substrate or modulator in studies of 2‑hydroxy‑ceramide biosynthesis and α‑oxidation pathways. Useful for reconstitution of model membranes or liposomes when specific α‑OH functionality is desired.
Surface chemistry/materials: Precursor for hydrophobic α‑hydroxy esters and urethanes; can impart adhesion or H‑bonding capability to hydrophobic coatings.
Derivatization standards: Forms stable esters and amides for GC/LC method development in lipidomics.
Transformations and tactics:
Chemoselective activation of the carboxyl: EDC·HCl/HOBt or DIC/DMAP for esterification; EDCI/HATU for amidation. SOCl2 or oxalyl chloride convert to the acid chloride (protect the α‑OH to avoid side reactions).
Protection strategies: Convert the secondary alcohol to a silyl ether (TBS/TBDPS) or benzyl ether; alternatively, form an acyl protecting group (e.g., Ac) when conditions tolerate.
Oxidation/reduction: TEMPO or Dess–Martin periodinane can oxidize the α‑OH to the corresponding 2‑keto acid; NaBH4/CeCl3 (Luche) reduces 2‑keto acids back with potential stereocontrol (applied to analogs).
Ensure anhydrous conditions for coupling chemistry. Pre‑dry in vacuo over P2O5 or molecular sieves if needed.
For biological assays, warm gently and vortex/sonicate to obtain clear DMSO stocks; avoid repeated freeze–thaw by aliquoting.
Reaction Conditions
General literature guidance for common transformations of α‑hydroxy fatty acids (adapt as needed to your substrate and scale):
Steglich esterification (to α‑hydroxy esters):
Typical: Carboxylic acid (1.0 eq), ROH (1.5–3.0 eq), DCC or EDCI (1.2–1.5 eq), catalytic DMAP (0.05–0.2 eq), CH2Cl2 or EtOAc, 0 °C to rt, 2–16 h.
Notes: Prefer EDCI to avoid DCU isolation; pre‑cool to minimize O→N acyl transfer; protect α‑OH if mixed selectivity is problematic.
Fischer esterification:
Typical: ROH (solvent), catalytic H2SO4 or p‑TsOH (1–5 mol%), reflux 4–24 h with water removal (Dean–Stark for higher alcohols).
Notes: Longer chains benefit from heating and vigorous stirring for dissolution.
Amide formation (EDCI/HATU):
Typical: Acid (1.0 eq), amine (1.1–1.5 eq), EDCI (1.2–1.5 eq) or HATU (1.1–1.2 eq), base (DIPEA 2–3 eq), DMF or DCM, 0 °C to rt, 2–12 h.
Notes: Protect or transiently acylate the α‑OH to avoid mixed anhydrides/oxazolones.
Acid chloride route:
Typical: SOCl2 (3–5 eq), catalytic DMF, reflux 1–2 h; then couple to ROH/RNH2 with base (pyridine/Et3N) at 0 °C→rt.
Oxidation to 2‑keto acid:
Typical: Dess–Martin periodinane (1.3 eq), CH2Cl2, 0 °C→rt, 1–3 h; or TEMPO/NaOCl (pH ~8.6, biphasic), 0–5 °C.
Purification/workup:
Warm solvents (EtOAc/Hex) aid dissolution; neutralize residual acids/bases carefully to prevent saponification.
Yields for these transformations are substrate‑ and setup‑dependent; consult the primary literature for exact procedures and expected ranges.
Safety and Handling
Item-specific hazard data from Product Data:
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 safety guidance for α‑hydroxy long‑chain fatty acids (literature/standard practice):
Likely to cause skin/eye irritation upon contact; avoid inhalation of dust/particulates. Handle in a chemical fume hood to minimize aerosolization when weighing or dissolving.
Personal protective equipment (PPE): Laboratory coat, safety glasses or splash goggles, and appropriate chemical‑resistant gloves (e.g., nitrile). For weighing fine powders, consider a particulate respirator per institutional policy.
First aid (general): In case of skin contact, wash with soap and water. For eye exposure, rinse cautiously with water for several minutes and seek medical attention if irritation persists. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical advice.
Incompatibilities: Strong oxidizing agents; strong bases (uncontrolled saponification) and strong acids (no hazard beyond normal acid handling but can promote dehydration under forcing conditions). Avoid prolonged heating which may cause dehydration/oxidation.
Thermal/chemical stability: Stable at ambient conditions when dry and protected from light/air; may slowly oxidize at the α‑position over extended storage.
Always consult the product‑specific SDS for authoritative hazard classification, exposure limits, and detailed response procedures.
Solvent Selection
2‑Hydroxypalmitic acid is a long‑chain, largely hydrophobic α‑hydroxy acid. Solvent choice is driven by balancing its lipophilicity with the ionizable carboxyl group.
Water: Very low solubility at neutral pH; increases markedly above pH ~6 as the carboxylate salt forms.
Alcohols (MeOH, EtOH, i‑PrOH): Good solubility when warmed; commonly used for stock solutions.
Aprotic polar solvents: DMSO and DMF readily dissolve at room temperature; DMSO is preferred for biological screening stocks.
Ethers/esters: THF and ethyl acetate dissolve upon warming; useful for extractions and esterifications.
Hydrocarbons: Limited solubility; may dissolve when hot or as the free acid in nonpolar blends.
Practical recommendations:
For biochemical assays: Prepare concentrated stocks in DMSO (e.g., 10–50 mM), then dilute into assay buffers containing carrier lipid/protein or cyclodextrin if needed to avoid precipitation. Consider converting to the sodium salt for aqueous applications.
For synthetic transformations: Use dry DCM, THF, MeCN, or toluene depending on coupling/protection strategy. Alcoholic solvents (MeOH/EtOH) are convenient for Fischer esterification.
Small comparison (general):
DMSO vs DMF: DMSO offers broader compatibility with screening; DMF is advantageous for amide couplings but is more challenging to remove.
THF vs 2‑MeTHF (green): Similar solvating power; 2‑MeTHF provides greener profile and improved phase separation in workups.
Storage and Reconstitution
Item-specific conditions (from Product Data):
Storage: Store at −80 °C.
Shipping: Dry ice packs + cold packs.
General handling guidance (for long‑chain α‑hydroxy acids):
Upon receipt: Keep frozen. Allow the sealed container to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation.
Aliquoting: To minimize freeze–thaw and headspace moisture, prepare single‑use aliquots under dry inert gas (N2/Ar) if the material will be redissolved multiple times (e.g., for screening).
Light and air: Store protected from light and air to limit slow oxidation at the α‑position. Use amber containers when feasible.
Reconstitution suggestions (general):
Analytical/synthetic use: Dissolve in dry DMSO, DMF, MeOH, EtOH, or CHCl3/MeOH mixtures. Gentle warming (30–50 °C) and sonication can aid dissolution.
Aqueous applications: Convert to the sodium or potassium salt, or prepare concentrated DMSO stocks and dilute into buffered media containing carriers (e.g., fatty acid–free BSA) to avoid precipitation.
Stability notes:
Long‑term stability is enhanced at −80 °C in the dry state. Avoid repeated temperature cycling. For solutions, store at −20 to −80 °C depending on solvent and intended use; verify stability by LC–MS/NMR before critical experiments.
Any item‑specific shelf life, assay at release, or stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
2‑Hydroxypalmitic acid is the α‑hydroxy derivative of palmitic acid (hexadecanoic acid), i.e., 2‑hydroxyhexadecanoic acid. It is a long‑chain α‑hydroxy carboxylic acid (C16), belonging to the 2‑hydroxy fatty acids family.
Item-specific identifiers (from Product Data):
SKU: H1500022
CAS: 764-67-0
Grade: Moligand™
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity data (for reference; not item-specific specifications):
Structural features: one terminal carboxylic acid (–CO2H) and one α‑oriented secondary alcohol at C2 (–CHOH–). The remaining chain is a linear saturated C14 alkyl segment terminating in –CH3.
Stereochemistry: Chiral at C2; material may be racemic or enantioenriched depending on source. Configuration (R/S) is not specified for this item.
2D description in words (general):
A 16‑carbon saturated backbone bearing a carboxyl at C1 and a hydroxyl substituent at C2. From the carboxyl carbon (C1), C2 is a secondary alcohol center bonded to the carboxyl carbon, a hydroxyl group, a long n‑tetradecyl chain (C3–C16), and a hydrogen atom.
Synthetic Utility
2‑Hydroxypalmitic acid is a bifunctional building block combining a carboxylic acid with an adjacent secondary alcohol on a long alkyl chain, enabling orthogonal transformations.
Retrosynthetic/value propositions (general):
Precursor to α‑hydroxy esters and amides that introduce controlled H‑bonding within hydrophobic matrices (polymers, coatings, lipids).
Platform for accessing 2‑keto acids (via oxidation) and subsequent stereocontrolled reductions to set C2 configuration.
Provides a handle for tethering hydrophilic headgroups (through the α‑OH) while maintaining a C16 hydrophobic tail.
Key reactions (literature/common practice):
Selective acylation of the α‑OH (Ac2O/pyridine or acid chlorides with base) versus global esterification of the carboxyl (Steglich, Fischer). Use protecting groups to control order.
Formation of acid chlorides (SOCl2, oxalyl chloride) for coupling to sterically hindered alcohols/amines, typically after protecting the α‑OH as TBS/TBDPS.
EDCI/HOBt or HATU‑mediated amidations to furnish α‑hydroxy amides (potential H‑bond donors/acceptors in supramolecular assemblies).
Oxidation of the α‑OH (Dess–Martin, TEMPO/bleach variants) to 2‑ketohexadecanoic acid, enabling subsequent enantioselective reductions or aldol‑type chemistry at C2 (via enolates of the keto acid derivatives).
Practical notes:
Dry, inert conditions improve coupling efficiency. Trace water promotes lactonization/dehydration side reactions under harsh activation.
For chiral applications, begin from enantioenriched 2‑HPA or resolve downstream; α‑substituted center strongly influences packing and properties.
Target Specificity
This product is a small molecule (α‑hydroxy fatty acid), not a biological macromolecule or antibody. Therefore, attributes such as antigen/epitope, clone, isotype, and species reactivity do not apply.
Item-specific data: Not specified for this item; refer to CoA/Spec Sheet if any target binding studies are provided.
For guidance on biochemical assay design using 2‑hydroxypalmitic acid (e.g., as a substrate, standard, or membrane component), see Reaction & Applications and Application Protocols.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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