2-Monostearin (Standard) , CAS No.621-61-4

CAS: 621-61-4 Cat. No.: M1437979 Summenformel: C21H42O4 PubChem CID: 79075

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

2-Monostearin (Standard) is the analytical standard of 2-Monostearin. This product is intended for research and analytical applications. 2-Monostearin is a biochemical reagent.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

Kanonisches Lächeln

CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO

IUPAC Name

1,3-dihydroxypropan-2-yl octadecanoate

InChIKey

YQEMORVAKMFKLG-UHFFFAOYSA-N

INCHI

1S/C21H42O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h20,22-23H,2-19H2,1H3

Isomere SMILES

CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO

WGK Deutschland

3

PubChem CID

79075

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Klasse Glycerolipids
      • Subclass Monoradylglycerols
        • Ebene5 Monoacylglycerols
          • Ebene6 2-monoacylglycerols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Klasse: Glycerolipids
• Subclass: Monoradylglycerols
• Intermediate Tree Nodes: Monoacylglycerols
• Direct Parent: 2-monoacylglycerols
• Alternative Parents: Fatty acid esters Carboxylic acid esters Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 2-acyl-sn-glycerol - Fatty acid ester - Fatty acyl - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as 2-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 2-position.
• External Descriptors: 2-monoglyceride

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

Application Protocols

No manufacturer‑validated application protocols are provided in the Product Data for this item.

General/literature guidance for common lab uses:

• Stock preparation (biochemical assays):
  • Dissolve 2‑Monostearin at 10–50 mg/mL in DMSO or chloroform. For aqueous assays, dilute into buffer containing 0.05–0.5% nonionic surfactant or fatty‑acid‑free BSA while vortexing/sonicating; keep final organic solvent ≤1–2% v/v for enzyme assays.
• Liposome/emulsion work:
  • Melt lipid (≥65–75 °C depending on composition) and blend with co‑lipids; add warm aqueous phase under high shear (probe sonication or rotor–stator). Rapidly cool to set structure.
• Analytical QC:
  • Assess purity and isomer ratio by 1H/13C NMR; confirm by HPLC‑ELSD/RI or GC after silylation. Store analytical standards under inert atmosphere at −20 °C.

For application‑critical work, develop and validate protocols in your own lab and consult primary literature.

Biological Roles

• Metabolic context (literature)

  • 2‑Monoacylglycerols (2‑MAGs) are key intermediates in dietary lipid digestion and absorption. Pancreatic lipase hydrolyzes triacylglycerols primarily to 2‑MAG + free fatty acids, which are taken up by enterocytes and re‑esterified.
  • 2‑MAGs can undergo acyl migration to 1‑MAG in aqueous/neutral conditions; enzymes may show positional specificity (e.g., MAGL hydrolyzes MAGs to glycerol + fatty acid).

• Signaling (literature)

  • While unsaturated 2‑MAGs (e.g., 2‑arachidonoylglycerol) serve as endocannabinoid ligands, saturated 2‑MAGs like 2‑monostearin mainly function structurally/energetically and as substrates in lipid turnover rather than as potent signaling molecules.

• Membrane/colloid behavior (literature)

  • Saturated MAGs form lamellar and gel phases; they influence bilayer packing, melting transitions, and can modulate permeability when incorporated into liposomes or emulsions.

Note: Information above is general background for research/lab understanding and is not a medical or clinical claim.

Buffer Applications

This compound is not a buffering agent and is not typically used to set or maintain pH.

• Practical note: In aqueous assays, 2‑Monostearin is dispersed rather than dissolved; use compatible assay buffers (e.g., phosphate, HEPES) supplemented with carriers (e.g., 0.05–0.5% nonionic surfactant or fatty‑acid‑free BSA) to maintain colloidal stability.
• For precise pH control, select conventional buffers appropriate to your assay; this product does not provide buffering capacity.

Green Alternatives

While 2‑Monostearin itself is a bio‑based lipid (derivable from renewable fatty acids), consider greener practices around its use and processing.

• Sourcing considerations (general)

  • Prefer feedstocks derived from sustainably produced stearic acid (e.g., certified palm‑free or RSPO‑certified supply chains) and glycerol from bioderived sources.

• Process/solvent choices

  • Favor biocatalytic routes (lipase‑catalyzed esterification/transesterification) in green solvents or solvent‑free melt conditions, reducing energy input and side‑products.
  • Replace chlorinated solvents with ethyl acetate, 2‑MeTHF, or ethanol/isopropanol where solubility permits; note that highly lipophilic MAGs may still require halogenated solvents for certain analytics.

• Stabilization and waste minimization

  • Use antioxidants only as needed (e.g., tocopherols) and under inert atmosphere to extend shelf life; minimize repeated heating cycles to reduce degradation and waste.

Small comparison (literature, qualitative)

• Route: Chemical esterification (acid/DMAP) — Pros: fast; Cons: harsher, more byproducts.
• Route: Enzymatic (lipase) — Pros: regioselective, milder, less waste; Cons: enzyme cost, solvent constraints.

Pharmaceutical Uses

For research and formulation development only; not for human or veterinary use.

• Excipient roles (literature)

  • Nonionic emulsifier/co‑emulsifier in creams, lotions, ointments, and suppositories; can increase viscosity and stabilize O/W or W/O emulsions.
  • Component of self‑emulsifying and solid self‑emulsifying drug delivery systems (SEDDS/SMEDDS/S‑SEDDS) to enhance dispersion of lipophilic actives upon aqueous dilution.
  • Matrix/structurant in lipid‑based formulations and solid dispersions; influences melt profile and drug release kinetics.

• Regulatory/compendial

  • “Glyceryl monostearate” exists in various pharmacopeial monographs (often as a mixture of mono‑ and di‑glycerides); however, positional isomer purity (sn‑2) and grade must be verified per application. This specific item’s pharmacopeial status is Not specified for this item; refer to CoA/Spec Sheet.

• Process notes

  • Incorporate by melting into the oil phase (60–80 °C depending on composition), then emulsify under shear; avoid prolonged high‑temperature exposure to limit acyl migration and hydrolysis.

Physical Properties

Item-specific values are not provided in the Product Data; do not treat literature values as product specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature for C21H42O4 ≈ 358.56 g/mol)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature: C21H42O4)
• Melting point: typically in the waxy‑solid range; values reported for monoacylglycerols of C18:0 vary around ~60–75 °C depending on isomer/polymorph (literature; not a specification for this item)
• Boiling point: decomposes before boiling at atmospheric pressure; not typically distilled (literature)
• Density: approximately 0.95–1.00 g/mL (solid/waxy; literature, temperature/polymorph dependent)
• Solubility (qualitative, literature)
  • Water: very low solubility; dispersible with surfactants/heat
  • Organic: soluble in chloroform, dichloromethane, toluene, hot ethanol/isopropanol; soluble in many lipid‑friendly solvents (e.g., ethyl acetate, THF); typically soluble in DMSO
• LogP: high (expected >6 for C18 MAG; literature, computational estimates vary)
• Refractive index: not typically reported for solid MAGs (literature)

Note: Actual item-specific values (mp, residual solvents, peroxide value, water content, etc.) are Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• “Standard” designation: In the absence of a stated analytical grade, “Standard” typically denotes a research‑use material meeting internal release specifications suitable for general biochemical/chemical applications (not guaranteed for chromatography UV cutoffs or trace‑metal specs unless stated).
• Typical quality considerations for monoacylglycerols (general/literature)
  • Isomeric composition: 2‑MAG can undergo acyl migration to 1‑MAG; ratio of 2‑ vs 1‑isomer may change upon storage or heating. If positional purity matters (e.g., enzymology at sn‑2), verify via NMR/GC.
  • Free fatty acid/diacylglycerol/triacylglycerol content: impurities commonly assessed by GC or HPLC with ELSD/RI.
  • Peroxide value and acid value: indicators of oxidative or hydrolytic degradation in lipids; check CoA if relevant.
  • Residual solvents and water: can affect polymorphism and handling; verify on CoA when critical.
• Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.

For regulated applications (e.g., excipient qualification), request detailed specifications, CoA, and batch analytical data.

Reaction and Applications

• Research applications (general/literature)

  • Lipid research: model saturated monoacylglycerol for studies of membrane physics, phase behavior, and lipid polymorphism.
  • Enzymology: substrate for lipases and monoacylglycerol lipase (MAGL); positional specificity assays (sn‑2 vs sn‑1) and acyl‑migration kinetics.
  • Formulation science: nonionic emulsifier/co‑emulsifier in O/W and W/O systems; stabilizes dispersions, enhances texture in semi‑solids; component of self‑emulsifying drug delivery systems (SEDDS/SMEDDS) as an excipient.
  • Materials/colloids: templating/structuring agent; forms lamellar/gel phases; can modulate rheology of oleogels.

• Synthetic/derivatization uses (general)

  • Precursor to di‑ and triacylglycerols via acylation (acyl chloride/anhydride or enzymatic transesterification).
  • Selective functionalization of primary diol (1,3‑OH) for protecting‑group strategies on glycerol frameworks.
  • Conversion to carbonate, ether, or silyl derivatives to tailor amphiphilicity.

• Practical tips

  • Minimize acyl migration: maintain lower temperatures, neutral to mildly acidic conditions, brief reaction times; use immobilized lipases for regioselective transformations.
  • Drying: vacuum over P2O5 or molecular sieves; avoid strong desiccants that may catalyze acyl migration in solution.
  • Analysis: verify isomer ratio and purity by 1H/13C NMR (diagnostic glycerol resonances), GC after silylation, or HPLC‑ELSD/RI.

• Manufacturer Applications (from catalog): Not specified; this section expands on typical research uses above.

Reaction Conditions

The following are literature‑based general conditions for common manipulations of monoacylglycerols; they are not product specifications.

• Enzymatic acylation to diacylglycerol (DAG)

  • Catalyst: immobilized CAL‑B (e.g., Novozym 435)
  • Acyl donor: fatty acid, vinyl ester, or acid anhydride (1–2 equiv per OH)
  • Solvent: tert‑butanol, 2‑MeTHF, or solvent‑free melt
  • Temperature: 35–60 °C; Time: 4–24 h
  • Notes: molecular sieves or reduced pressure to remove water/ethanol; high regioselectivity for primary OHs.

• Chemical acylation (to DAG/TAG)

  • Reagents: fatty acyl chloride or anhydride (1.1–2.2 equiv per OH)
  • Base: pyridine or Et3N; Catalyst: DMAP (0.05–0.2 equiv)
  • Solvent: CH2Cl2 or toluene; Temperature: 0–25 °C (stepwise), then warm to 40–60 °C if needed
  • Notes: monitor to limit over‑acylation and acyl migration; quench with weak acid then purify by silica (pre‑deactivated with 1–2% Et3N).

• Etherification of primary OHs

  • Conditions: NaH or KOtBu (0.5–1.5 equiv), alkyl halide (1.1–2.0 equiv), solvent THF/DMF
  • Temperature: 0–25 °C; Time: 1–6 h
  • Notes: protect the secondary alcohol if selectivity is required.

• Analytical derivatization for GC

  • Silylation: BSTFA + 1% TMCS, 60–70 °C, 15–30 min to form TMS ethers; improves volatility for GC‑FID/MS.

Yields and exact conditions vary with substrate and scale; consult primary literature for optimization.

Safety and Handling

• GHS status (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 considerations (literature/general guidance)

  • 2‑Monostearin is a nonionic lipid, generally regarded as having low acute toxicity; nonetheless, handle as a laboratory chemical.
  • Potential hazards: combustible solid; dust may form combustible dust‑air mixtures. May cause mild eye/skin irritation.
  • PPE: lab coat, safety glasses or goggles, and appropriate gloves (e.g., nitrile). Use in a well‑ventilated area; avoid generating dust/aerosols.
  • Incompatibilities: strong oxidizing agents; strong bases/acids can catalyze hydrolysis or acyl migration in solution.
  • First aid (overview; refer to SDS for details):
    • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
    • Inhalation: move to fresh air; seek medical attention if symptoms occur.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
  • Firefighting: treat as a combustible organic solid; use CO2, dry chemical, or foam. Thermal decomposition may generate irritating fumes.

Always consult and follow the product‑specific SDS for authoritative safety information.

Solvent Selection

This product is a nonionic lipid/solid; solvent considerations focus on dissolving/dispersing for formulation or reaction setup.

• Polarity/miscibility profile (literature)

  • Highly lipophilic; practically insoluble in water, but dispersible with surfactants or upon melting.
  • Good solubility: chloroform, dichloromethane, toluene, THF, ethyl acetate, diethyl ether, hexanes (warming may help), hot ethanol/isopropanol; typically soluble in DMSO for biochemical assays.

• Practical selection tips

  • For analytical sample prep (GC/FAME derivatization workflows): dissolve in chloroform or chloroform:methanol (2:1) for robust solubilization.
  • For enzymology (lipase/MAGL assays): DMSO stocks (≤10–20 mg/mL) diluted into assay buffer containing dispersants (e.g., 0.1% Triton X‑100, Tween 20) or BSA; avoid high organic fractions that denature proteins.
  • For formulation/emulsions: melt and incorporate into oil phase; mix with co‑surfactants (e.g., polysorbates) and add aqueous phase under shear.
  • For synthetic transformations: use aprotic organic solvents (toluene, THF, MeCN, CH2Cl2) depending on catalyst/base; exclude moisture to minimize hydrolysis/acyl migration.

• When to choose alternatives

  • If aqueous compatibility is needed, consider using a self‑emulsifying system (e.g., MAG + PEGylated surfactant) or shorter‑chain MAGs for improved dispersibility.
  • For cubic‑phase crystallography, monoolein (unsaturated MAG) is often preferred; saturated MAGs favor gel/lamellar phases at room temperature.

Storage and Reconstitution

• Storage conditions (from Product Data)

  • Store at −20 °C.
  • Shipped in: Ice chest + ice pads.

• Additional handling guidance (general/literature)

  • Protect from light, heat, and moisture. For long‑term storage, keep tightly sealed under inert gas (nitrogen/argon) to minimize oxidation and hydrolysis.
  • Avoid repeated freeze–thaw and thermal cycling; dispense into single‑use aliquots.

• Reconstitution/solubilization (general)

  • Organic stocks: dissolve in chloroform, dichloromethane, toluene, THF, ethyl acetate, or DMSO. For alcoholic solvents (ethanol/isopropanol), warming may be required.
  • Aqueous use: prepare an organic stock and disperse into pre‑warmed buffer containing surfactant (e.g., 0.1% Tween 20) or BSA with vigorous mixing/sonication. Alternatively, melt the material and emulsify into the aqueous phase under shear.

• Stability notes

  • Monitor for increases in acid value (hydrolysis) or changes in isomer ratio (2→1 acyl migration) over time, especially if stored above −20 °C or subjected to heat.

Refer to the product‑specific CoA/SDS for any additional storage or stability instructions.

Structure and Identity

Brief description: 2‑Monostearin is the sn‑2 monoacylglycerol of stearic acid (octadecanoic acid) — a nonionic lipid consisting of a glycerol backbone esterified at the secondary (2) hydroxyl with an n‑C18:0 fatty acyl group; the primary (1,3) hydroxyls remain free.

• Item-specific identifiers (from Product Data)

  • SKU: M1437979
  • Product name: 2-Monostearin (Standard)
  • CAS: 621-61-4
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Core structural features (general/literature)

  • Molecular formula (sn‑2 monostearin): C21H42O4 (literature)
  • Molecular weight: ~358.56 g/mol (literature, for C21H42O4)
  • Functional groups: one long‑chain saturated fatty acyl ester; two free alcohols (vicinal diol at C1 and C3 of glycerol)
  • Stereochemistry: the sn‑2 center is prochiral in glycerol but becomes a stereogenic center upon monoacylation; commercial material is typically racemic unless otherwise specified (literature)
  • 2D description: a three‑carbon glycerol scaffold with an ester linkage at the central carbon; terminal and penultimate carbons bear free hydroxyls; the acyl substituent is a linear C17H35 chain attached via –C(=O)– to the glycerol O at C2.

• Synonyms (general/literature)

  • 2‑Monoacylglycerol, stearoyl (sn‑2 MAG, C18:0)
  • 2‑Glyceryl monostearate; 2‑monostearoylglycerol

Synthetic Utility

• Functional group landscape

  • One ester (stearate) and two free hydroxyls enable divergent functionalization: selective acylation/alkylation of primary diols, carbonate formation, silylation, and further esterifications.

• Retrosynthetic/value as building block (literature)

  • Serves as a glycerol‑based linchpin to access 1,2‑ or 1,3‑diacylglycerols and triacylglycerols with controlled substitution via stepwise acylation or enzymatic routes.
  • Useful for preparing labeled lipids (e.g., 13C/2H tagging on glycerol or acyl chain) for metabolism studies.

• Named/typical transformations

  • Enzymatic acylation/transesterification with immobilized Candida antarctica lipase B (CAL‑B) for regioselective synthesis of structured lipids.
  • Chemical acylation using acyl chlorides/anhydrides (DMAP or pyridine catalysis) to give DAGs/TAGs.
  • Etherification of primary hydroxyls (Williamson ether) to generate nonhydrolyzable analogs.

• Considerations

  • Control acyl migration (2→1 MAG) by using low temperatures, short times, and appropriate catalysts/solvents; verify regiochemistry by NMR.
  • Protecting‑group strategies may be required for selective manipulations (e.g., silyl protection of one primary OH).

Target Specificity

Not applicable — this product is a small‑molecule lipid, not an antibody, enzyme, or ligand with defined biological “target specificity” under product data. No antigen/epitope/clone/isotype information is provided.