Monocaprylin(GMC) - ≥98%, Monoacylglycerol+diacylglycerol+triacylglycerol , CAS No.26402-26-6

CAS: 26402-26-6 Cat. No.: M1516128 Formula: C₁₁H₂₂O₄ Molecular Weight: 218.29 Beilstein Registry Number: 2(2)303 EC Number: 247-668-1

GRADE & PURITY ≥98%, Monoacylglycerol+diacylglycerol+triacylglycerol

Storage

Room temperature

Shipped In

Normal

Specifications

Specifications & Purity

≥98%, Monoacylglycerol+diacylglycerol+triacylglycerol

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

Canonical Smiles

CCCCCCCC(=O)OCC(CO)O

IUPAC Name

2,3-dihydroxypropyl octanoate

InChIKey

GHBFNMLVSPCDGN-UHFFFAOYSA-N

INCHI

1S/C11H22O4/c1-2-3-4-5-6-7-11(14)15-9-10(13)8-12/h10,12-13H,2-9H2,1H3

Isomeric SMILES

CCCCCCCC(=O)OCC(CO)O

Molecular Weight

218.29

Beilstein

2(2)303

Reaxy-Rn

1724525

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1724525&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerolipids
      • Subclass Monoradylglycerols
        • Level5 Monoacylglycerols
          • Level6 1-monoacylglycerols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerolipids
• Subclass: Monoradylglycerols
• Intermediate Tree Nodes: Monoacylglycerols
• Direct Parent: 1-monoacylglycerols
• Alternative Parents: Fatty acid esters Secondary alcohols Carboxylic acid esters 1,2-diols Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1-acyl-sn-glycerol - Fatty acid ester - Fatty acyl - 1,2-diol - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Primary alcohol - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Alcohol - Organic oxide - Organooxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.
• External Descriptors: octanoate ester - 1-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

Chemical and Physical Properties

• Melt Point(°C): 41 °C
• Molecular Weight: 218.290 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 218.152 Da
• Monoisotopic Mass: 218.152 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 159.000
• 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 vendor-validated assay protocols or dilutions are provided for this item.

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

• General laboratory usage examples (for guidance only):

  • Nanoemulsion screening: Combine oil phase (e.g., monocaprylin + triglyceride), surfactant (e.g., polysorbate), and aqueous phase under high-shear mixing; refine ratios via pseudo-ternary phase diagrams.
  • Enzymatic transesterification: Charge monocaprylin and acyl donor with immobilized lipase; incubate 40–60 °C with gentle agitation; remove byproduct alcohol under reduced pressure to shift equilibrium.
  • Stock solution preparation: Dissolve monocaprylin at 50–200 mg/mL in ethanol or isopropanol; add to buffer under stirring to a final organic content ≤2–5% v/v as assay-compatible.

These examples are illustrative; adjust conditions to your system and follow institutional safety practices.

Biological Roles

Monocaprylin is a monoacylglycerol (MAG), a key intermediate in lipid metabolism and digestion.

• Literature/general biochemical context:

  • Formation: Generated in vivo during lipolysis of dietary triglycerides by lipases, and can undergo acyl migration between the 1- and 2-positions of glycerol.
  • Metabolism: Hydrolyzed by monoacylglycerol lipase or further acylated to di- and triacylglycerols; the octanoyl moiety can undergo mitochondrial β-oxidation.
  • Self-assembly: MAGs form lyotropic liquid crystalline phases with water and co-solvents; this property underlies their utility in membrane protein crystallization and delivery research.
  • Membrane interactions: As nonionic amphiphiles, MAGs can insert into lipid bilayers and affect fluidity/permeation characteristics in model systems (research observations).

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

All information pertains to research and laboratory contexts only. No medical or clinical claims are made.

Buffer Applications

Monocaprylin is not a buffering agent and does not define pH. However, it can be incorporated into buffers as a solubilizer or to create dispersions of hydrophobic analytes.

• Practical guidance (general):

  • Prepare a stock in ethanol, isopropanol, or DMSO; add slowly to buffered aqueous media (e.g., PBS, HEPES) under vigorous stirring or sonication.
  • Use co-surfactants (e.g., polysorbate 80) or co-solvents (e.g., propylene glycol) to stabilize nanoemulsions or mixed micelles.
  • Maintain temperature above its softening point during preparation to reduce viscosity and aid dispersion; cool while stirring to lock in the microstructure.

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

Green Alternatives

Monocaprylin itself is often bio-based (derived from glycerol and caprylic acid sourced from natural oils), and can serve as a greener alternative to petrochemical surfactants in some contexts.

• Sustainability aspects (general):

  • Renewable feedstocks: Glycerol (biodiesel byproduct) and fatty acids from plant oils can underpin a renewable supply chain.
  • Low VOC: Low volatility relative to many organic solvents; can reduce VOC emissions when used as a vehicle/co-solvent.

• Alternatives/complements (literature/general):

  • 2-MeTHF or CPME (for organic synthesis solvent needs) vs chlorinated solvents when monocaprylin is considered only as a solvating excipient.
  • Sugar-based surfactants (alkyl polyglucosides) or polyglycerol esters for higher biodegradability in aqueous systems.

• Comparison snapshot (general):

  • Monocaprylin: Nonionic, bio-based, excellent oil solubilizer; limited water solubility; favorable for lipase chemistry and O/W emulsions with co-surfactants.
  • PEG surfactants (e.g., polysorbates): High water compatibility but petrochemical-derived; potential oxidative byproducts.
  • APGs: Readily biodegradable, good foaming; may be less effective in solubilizing very hydrophobic oils compared with monoacylglycerols of medium chain length.

Selection should balance performance, renewability, toxicity profile, and downstream processing constraints.

Pharmaceutical Uses

For research use only. The following describes typical formulation roles of glycerol monocaprylate in a laboratory or development context (no medical claims).

• Excipient roles (literature/general):

  • Emulsifier/co-surfactant in oil-in-water emulsions, nanoemulsions, and SEDDS/SMEDDS prototypes for solubilizing lipophilic APIs.
  • Vehicle for topical, transdermal, or oral prototype formulations; improves wetting and dispersion of hydrophobic actives when combined with hydrophilic surfactants and co-solvents.
  • Component in lipid-based delivery systems (e.g., mixed MAG/triglyceride matrices) and lyotropic liquid crystal phases for research.

• Development considerations:

  • Assess acid value and peroxide value to minimize API degradation.
  • Map pseudo-ternary phase diagrams to identify robust self-emulsifying regions with selected oils and surfactants.
  • Verify extractables/leachables compatibility with container-closure materials (nonionic lipids can plasticize some polymers).

• Regulatory/compendial status: Not specified for this item; consult relevant pharmacopeias and the product CoA if compendial compliance is required.

Physical Properties

A medium-chain monoacylglycerol, typically a waxy solid or viscous liquid near ambient temperature depending on isomer ratio and purity.

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

• Literature/general values (for glycerol monocaprylate; indicative only):

  • Molecular weight: ~218.29 g/mol
  • Appearance: colorless to pale yellow viscous liquid or soft solid (varies with isomer content)
  • Solubility: Miscible with many organic solvents (ethanol, isopropanol, acetone, chloroform, ethyl acetate); limited solubility in water but can self-assemble and emulsify; soluble in edible oils and MCTs (literature).
  • Amphiphilicity: Nonionic surfactant; can form micelles/microemulsions with co-solvents or co-surfactants (literature).
  • Density, refractive index, melting point, boiling point, logP, pKa: Not reliably standardized across grades for monocaprylin; consult CoA/SDS or primary literature for the specific lot.

Notes for users:

• Physical state can change with temperature; gentle warming (~30–45 °C) commonly reduces viscosity to facilitate handling (general lab practice).
• Free hydroxyls enable hydrogen bonding, impacting solvent choice and chromatographic behavior (general chemistry knowledge).

Quality & Grades

Grade and purity are not specified in the Product Data for this SKU; please consult the CoA/Spec Sheet for assay, isomer composition (1- vs 2-monoglyceride), acid value, water content, and residual solvents.

• Item-specific notes:

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

• Interpreting common quality metrics for monocaprylin (general guidance):

  • Assay (monoglyceride content): Higher % MAG minimizes di-/triacylglycerol impurities and improves reproducibility in self-assembly and enzymatic reactions.
  • Isomer ratio (1-MAG vs 2-MAG): Impacts physical properties and reactivity due to acyl migration propensity. Suppliers may report positional isomer distribution.
  • Acid value/peroxide value: Indicators of hydrolysis/oxidation; low values are preferable for stability and odor control in formulations.
  • Water content (e.g., KF): Affects microemulsion formation and lipase-catalyzed reactions.
  • Residual solvents/metals: Relevant for synthetic and analytical applications; HPLC/GC methods can quantify.

• Grade context (general):

  • Reagent grade: Suitable for most research uses.
  • High-purity or chromatography grade: Tighter control of UV absorbance and volatiles, beneficial for analytical development.
  • Bio-based feedstock: Many monocaprylin products are derived from natural fats/oils; confirm origin if required for your application.

Reaction & Applications

Monocaprylin functions both as a substrate/reagent (due to its ester and diol functionalities) and as a nonionic surfactant/vehicle in formulation science.

• As a reagent/building block (literature/general):

  • Ester hydrolysis/saponification to glycerol and octanoate; useful for kinetic or enzymology studies (lipases, esterases).
  • Transesterification and interesterification with other acyl donors using organocatalysts or lipases (e.g., CAL-B) to access designer monoacylglycerols or structured lipids.
  • Selective derivatization of the free hydroxyl groups (e.g., acylation, carbonate formation, tosylation) for subsequent transformations and polymer/conjugate synthesis.

• As a functional excipient (research use):

  • Emulsifier/co-surfactant in oil-in-water systems; helps solubilize lipophilic actives in nanoemulsions and self-emulsifying systems (SEDDS/SMEDDS) when combined with co-solvents (ethanol, propylene glycol) and hydrophilic surfactants.
  • Solvent/vehicle for hydrophobic small molecules in biological assays, with gradual dispersion into aqueous media under agitation.

• Practical tips (general):

  • Minimize prolonged exposure to strong acids/bases to limit hydrolysis and acyl migration (1↔2 MAG).
  • For enzymatic processes, maintain mild temperatures (typically 30–60 °C) and controlled water activity; remove byproducts (e.g., using vacuum or molecular sieves) to drive equilibrium.
  • For formulation screening, map pseudo-ternary phase diagrams (oil–surfactant–water) to identify microemulsion regions.

Reaction Conditions

Typical laboratory conditions involving monocaprylin are summarized for guidance (literature/general). Optimize for your specific system.

• Hydrolysis/saponification:

  • Base-catalyzed: MeOH/H2O with NaOH or KOH (0.5–1.0 equiv), 20–40 °C, 0.5–4 h; monitor by TLC/GC. Quench and acidify to pH ~2 to isolate octanoic acid; glycerol partitions to aqueous phase.
  • Enzymatic: Lipase (e.g., CAL-B) in buffer or biphasic system, 25–40 °C; control water activity to favor hydrolysis vs transesterification.

• Transesterification/interestification:

  • Enzymatic: CAL-B (immobilized), neat or in tert-butanol/hexane; 40–60 °C; removal of formed alcohol (vacuum or molecular sieves) drives equilibrium. Reaction times from hours to overnight are common; yields often high when equilibrium managed.
  • Chemical: Acid/base catalysis in anhydrous solvents (e.g., toluene, MeCN); mild bases (DBU) or acids (p-TsOH) at 25–60 °C; minimize to limit acyl migration.

• Diol derivatization:

  • Silylation: TBDMS-Cl, imidazole, DMF, 0–25 °C.
  • Carbonate formation: Triphosgene or CDI with alcohols; 0–25 °C, aprotic solvent.
  • Selective acylation: Ac2O/DMAP or acid chloride/DMAP, 0–25 °C; positional selectivity may require protecting groups.

• Workup/purification:

  • Use brine washes to break emulsions; add small amounts of alcohol to aid phase separation.
  • Silica chromatography with hexane/EtOAc/MeOH gradients; consider deactivated silica to reduce tailing of hydroxylated species.

Safety & Handling

Safety information specific to this catalog item is not provided in the Product Data and may vary by supplier and grade.

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature, Cool
  • Shipped In: Normal
  • GHS Classification, Signal Word, H-Statements, Pictograms: Not specified for this item; refer to SDS.

• General safety considerations for monoacylglycerols (literature/typical):

  • Expected hazards: Generally low acute toxicity; may cause skin or eye irritation on contact; combustible organic material. Avoid inhalation of aerosols/mists and prolonged skin contact.
  • Incompatibilities: Strong oxidizers (risk of exotherm/oxidation), strong acids/bases (can catalyze hydrolysis/acyl migration), and strong reducing agents (general chemical reactivity guidance).
  • Thermal behavior: Viscosity decreases on warming; avoid overheating to prevent decomposition; do not heat in the presence of strong bases or acids.

• PPE and handling (good laboratory practice):

  • Wear safety glasses, lab coat, and appropriate gloves (e.g., nitrile). Use in a well-ventilated area or fume hood when preparing sprays/aerosols or using volatile co-solvents.
  • First aid (overview; defer to SDS): Rinse eyes cautiously with water if contacted; wash skin with soap and water; if inhaled as aerosol, move to fresh air; if ingested in lab context, rinse mouth and seek medical attention.

Always consult the product-specific SDS for authoritative hazard and first-aid information.

Solvent Selection

Monocaprylin is a nonionic amphiphile: a C8 fatty acyl chain attached to a glycerol bearing two free hydroxyls. It dissolves readily in many organic solvents and can emulsify or solubilize hydrophobic materials.

• Polarity/miscibility (literature/general):

  • Highly soluble: ethanol, isopropanol, methanol, acetone, ethyl acetate, chloroform, dichloromethane, MTBE, toluene; miscible with medium-chain triglycerides and vegetable oils.
  • Limited water solubility, but can form micelles or microemulsions with co-solvents (e.g., ethanol, propylene glycol) and co-surfactants (e.g., polysorbates).

• Selection tips (general lab practice):

  • For stock solutions: Use ethanol, isopropanol, or DMSO to prepare concentrated stocks for biochemical assays; dilute into aqueous buffers under stirring.
  • For extractions/formulations: Ethyl acetate or ethanol often offers good balance of safety and solvency; chloroform is effective for lipid analytics (e.g., Folch/Bligh–Dyer systems).
  • For enzymatic transformations: Solvent-free or tert-butanol/hexane systems are common to preserve lipase activity (literature).

• Comparison (general):

  • Versus longer-chain MAGs (e.g., monoolein): Monocaprylin is less viscous and generally more polar, aiding handling and dispersion.
  • Versus PEG surfactants: Lower hydrophilicity; better solvent compatibility with oils, but poorer water solubility.

Always verify solvent grade compatibility with your downstream analytics and equipment materials.

Storage & Reconstitution

Maintain product integrity by minimizing hydrolysis, oxidation, and acyl migration.

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature, Cool
  • Shipped In: Normal

• General guidance for monocaprylin:

  • Storage: Keep tightly closed in a dry, cool place away from direct light. For long-term storage, consider an inert headspace (nitrogen/argon) to limit oxidation. Avoid prolonged exposure to strong acids/bases.
  • Container compatibility: Glass preferred; high-density polyethylene (HDPE) or fluoropolymer-lined caps reduce extractables.
  • Stability: Stable under recommended conditions; monitor acid value/peroxide value for sensitive applications (literature/general).

• Handling/reconstitution:

  • If viscous or semi-solid, gently warm to 30–45 °C to liquefy before dispensing; avoid overheating.
  • Solubility tips: Readily dissolves in ethanol, isopropanol, acetone, ethyl acetate, chloroform, and oils; limited water solubility—use co-solvents or surfactants for aqueous systems.
  • Freeze–thaw: Not typically required; if frozen for storage, allow to equilibrate to room temperature and mix before use to ensure homogeneity.

• Item-specific specifications (water content, inhibitors, stabilizers): Not specified for this item; refer to CoA/Spec Sheet.

Structure & Identity

Monocaprylin (glycerol monocaprylate, GMC) is a monoacylglycerol formed by esterification of glycerol with caprylic (octanoic) acid; it retains two free hydroxyls and one octanoyl ester.

• Item-specific (from Product Data):

  • SKU: M1516128
  • Product Name: Monocaprylin (GMC)
  • CAS: 26402-26-6
  • InChIKey: 101890 (as listed; consult CoA/SDS for definitive identifier)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (general information for glycerol 1- or 2-monooctanoate):

  • Synonyms: Glyceryl monocaprylate; 1-monooctanoyl-rac-glycerol; monoacylglycerol C8 (MAG C8)
  • Molecular formula (literature): C11H22O4 (monoester of glycerol with octanoic acid)
  • Molecular weight (literature): ~218.29 g/mol
  • Structural features: Nonionic amphiphile; one ester function (–COO–), two unprotected alcohols (–CH2OH/–CHOH). Often supplied as a positional isomer mixture (1- and 2-monoglyceride) due to acyl migration.
  • 2D description in words: A glycerol backbone with an octanoyl group esterified to one hydroxyl; the remaining two hydroxyls are free, conferring modest polarity to an otherwise medium-chain lipid tail.

Synthetic Utility

Monocaprylin provides a versatile platform combining an ester with two free alcohols on a glycerol backbone, enabling diverse transformations.

• Functional group reactivity (literature/general):

  • Ester: Hydrolysis (acid/base/enzymatic), transesterification (metal-/enzyme-catalyzed), aminolysis to amides under activating conditions.
  • Diol: Selective protection (e.g., acetonide, silyl ethers), carbamate/carbonate formation, tosylation/mesylation enabling further substitution or oligomerization.
  • Acyl migration: Base/acid catalyzed 1↔2 isomerization; manage with mild conditions and rapid workups to control regioisomer purity.

• Applications:

  • Lipase-catalyzed synthesis of structured lipids and designer MAGs (e.g., solvent-free interesterification at 40–60 °C).
  • Preparation of lipid–polymer conjugates, surfactants, and pro-moieties by leveraging the diol for attachment while retaining the C8 chain for hydrophobicity.
  • Model substrate in kinetics of esterase/lipase activity and for studying micellar/colloidal effects on reaction rates.

• Practical notes:

  • Low volatility simplifies solvent removal; however, high viscosity may necessitate gentle heating and vacuum.
  • Purification commonly via normal-phase silica (use deactivated silica or add 0.1–1% acetic acid/triethylamine to minimize tailing of polyols).

Target Specificity

This product is a small-molecule lipid excipient/reagent, not a biological targeting reagent or antibody.

• Item-specific targeting data: Not applicable.

If your application requires a targeting biomolecule (e.g., antibody, ligand), please see antibody/bioconjugate categories.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store in a cool place.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 26402-26-6, the molecular formula is C11H22O4, and the molecular weight is 218.29 g/mol. InChIKey GHBFNMLVSPCDGN-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.