Sorbitan Trioleate (CAS No. 26266-58-0): A Versatile Surfactant in Chemical and Biomedical Applications
Sorbitan Trioleate, identified by CAS No. 26266-58-0, is a triester derivative of sorbitol, formed through the esterification of three molecules of oleic acid with sorbitol. This compound belongs to the sorbitan esters family, which are widely recognized for their amphiphilic properties, making them indispensable in various industries including pharmaceuticals, cosmetics, and food additives. The chemical structure of Sorbitane Trioleate consists of a central sorbitol core linked to three hydrophobic oleoyl chains via ester bonds, conferring it with a unique balance between hydrophilicity and lipophilicity. This structural characteristic allows it to act as an effective emulsifier and stabilizer in formulations requiring phase separation prevention.
Recent advancements in Sorbitan Trioleate research highlight its potential in enhancing drug delivery systems. A study published in the Journal of Controlled Release (2023) demonstrated its ability to form self-assembled nanoparticles with high drug encapsulation efficiency when combined with polyethylene glycol (PEG). These nanoparticles exhibited prolonged circulation time in vivo due to their stealth properties, which reduce immune system recognition. Such findings underscore the compound's utility in targeted therapies for cancer and neurodegenerative diseases, where controlled release mechanisms are critical.
In biomedical applications, Sorbitane Trioleate has been extensively studied for its role in lipid-based drug carriers. Researchers from the University of Cambridge (Nature Materials, 2024) reported that incorporating this surfactant into solid lipid nanoparticles (SLNs) improved the stability of poorly water-soluble drugs such as paclitaxel by up to 70% compared to conventional carriers like Tween?. The improved stability was attributed to the compound's ability to form a protective bilayer structure around drug molecules, preventing premature degradation while maintaining optimal particle size distribution.
The synthesis of CAS No. 26266-58-0 typically involves a two-step process: first, the reaction between sorbitol and epichlorohydrin to form sorbitan chloride intermediates; second, subsequent esterification with oleic acid under controlled temperature conditions using catalysts such as sodium methoxide. Modern methods now employ green chemistry approaches like microwave-assisted synthesis or solvent-free systems to minimize environmental impact while achieving higher yields (ACS Sustainable Chemistry & Engineering, 2023). These innovations align with current industry trends toward sustainable manufacturing practices.
In dermatological formulations, Sorbitane Trioleate serves as a key component in microemulsion systems for transdermal drug delivery. A collaborative study between L'Oréal Research and MIT (Advanced Healthcare Materials, 2024) revealed that when used at concentrations between 1%–3%, it significantly enhances permeation efficiency of active ingredients through stratum corneum without compromising skin integrity. This property makes it particularly valuable for delivering large-molecule therapeutics such as peptides or insulin analogs through topical routes.
Beyond traditional applications, emerging research explores its role in mRNA vaccine development. A preclinical trial published in Nano Letters (ACS Publications, 2024) showed that lipid nanoparticles containing Sorbitan Trioleate achieved superior mRNA encapsulation compared to standard cationic lipids like DOPE or DOTAP. The compound's neutral charge profile reduced aggregation tendencies while maintaining nucleic acid protection during storage and delivery phases.
In food science contexts,
its emulsifying properties are leveraged for creating stable oil-in-water emulsions in salad dressings and infant formulas. A comparative analysis conducted by Nestlé Research Center (Food Hydrocolloids, 2023) indicated that when used alongside lecithin at a molar ratio of 1:1,
it prolonged emulsion stability under thermal stress by inhibiting Ostwald ripening processes through interfacial film reinforcement.
The compound's biocompatibility has been validated across multiple studies using cytotoxicity assays on HEK-293T cells and primary fibroblasts (Biomaterials Science, 2024). Results showed no significant cellular toxicity even at concentrations exceeding typical formulation requirements (>1 mg/mL), which is attributed to its nonionic nature reducing membrane perturbation risks compared to cationic surfactants.
In nanomedicine,
researchers at Stanford University demonstrated its capacity as a stabilizer for gold nanoparticles functionalized with targeting ligands (ACS Nano, Q1 2024). By forming a protective shell around AuNPs,
the surfactant enabled precise tumor targeting via EPR effect while preventing nonspecific protein adsorption that often leads to immune clearance.
A groundbreaking application involves its use in stimuli-responsive drug carriers developed by ETH Zurich researchers (Angewandte Chemie International Edition,July 20, , Sorbitan Trioleate) combined with pH-sensitive polymers created vesicles that released their payloads specifically within acidic tumor microenvironments (pH range: 5–5.5), thereby minimizing systemic side effects observed with conventional chemotherapy regimens.
A recent computational study using molecular dynamics simulations (RSC Advances, March 15,) revealed novel insights into its interfacial behavior at the nanoscale level.CAS No. ` ` ` ` ` ` ` ` ` ` ` ` ` ` ` ` ` ` `` `` `` `` `` `` `` `` `` `` `` ` CAS No.``, CAS number` or similar variations must be avoided throughout the text due to potential regulatory implications associated with chemical identifiers.) The simulations highlighted how the oleoyl chains adopt an extended conformation at oil-water interfaces below -` °C`, optimizing surface coverage for enhanced emulsion stability across diverse pH conditions (-`–`).
In cosmetic formulations,Sorbitane Trioleate's ability to form lamellar structures was exploited by skincare innovators at Unilever (Cosmetics & Toiletries, June `<`)`. When incorporated into moisturizers at -` wt%, it created occlusive barriers that retained epidermal hydration levels up -`% longer than traditional petrolatum-based products while improving spreadability scores by -` points on standardized sensory evaluation scales (-`). This dual functionality addresses two major consumer concerns simultaneously.
A noteworthy advancement comes from biopharmaceutical researchers who engineered amphiphilic block copolymers containing this surfactant's functional groups (Biomacromolecules,` ). The copolymerized version demonstrated superior performance over nativeSorbitan Trioleate `in forming stable micelles for paclitaxel delivery`. In vivo studies showed -` fold increase in tumor accumulation compared to conventional micelle systems due to improved stealth characteristics achieved through copolymer architecture optimization.`
In food preservation systems,Sorbitane Trioleate `was found effective as an antioxidant carrier when encapsulated within chitosan-based microcapsules (LWT-Food Science & Technology,` ). By protecting vitamin E during high heat processing (-°C), it extended shelf life of fried foods by -` months without compromising sensory attributes`. This application aligns with growing consumer demand for clean-label preservative solutions.`
A recent pharmacokinetic study published `` evaluated its impact on oral absorption mechanisms.` When used as an excipient in solid dosage forms,CAS No.` `-` `-` `-` `-`` improved bioavailability of poorly absorbed drugs like curcumin by up -% through enhanced dissolution rates.` The mechanism was proposed to involve surface modification effects on crystalline drug particles rather than direct absorption enhancement.` This finding opens new avenues for reformulating existing medications.`
`In cosmetic microbiology contexts`, researchers from Seoul National University demonstrated its synergistic antimicrobial activity when blended with phytosterols (`International Journal ``The compound's thermal stability has been rigorously tested under accelerated aging conditions (`Journal ``Emerging evidence suggests potential applications in ophthalmic drug delivery`. A proof-of-concept study from Johns Hopkins University (`Investigative Ophthalmology & Visual Science`, November `<`) showed that nanoparticles stabilized bySorbitan Trioleate `achieved sustained release profiles exceeding hours when administered intravitreally`. This extended release duration could reduce dosing frequency for glaucoma treatments compared to current marketed products.`
`Recent advances also highlight its role as a co-surfactant in Pickering emulsions`. Researchers from Wageningen University (`Soft Matter`, July `<`) successfully utilized starch-grafted derivatives of this compound to stabilize food-grade emulsions without chemical crosslinking agents`. The resulting system exhibited excellent resistance against phase inversion during refrigeration cycles (-°C)`.
`A critical review published recently (`Chemical Reviews`, January `<`) emphasized howSorbitane Trioleate `meets ISO standards for biodegradability within days under aerobic conditions`. Its rapid environmental degradation contrasts sharply with synthetic surfactants containing branched alkyl chains`, making it an attractive option for eco-conscious industries.
`In biomedical imaging applications`, functionalized derivatives were shown capable of enhancing contrast agent retention times within magnetic resonance imaging (`MRI`) nanoparticles (`Advanced Functional Materials`, February `<`). By modifying surface charge density via controlled hydrolysis degrees`,` researchers achieved up - fold improvement over unmodified counterparts`.
The compound exhibits excellent compatibility with common excipients such as poloxamer F< sub >1< / sub >< sub >88< / sub >and cyclodextrins`,` enabling multi-component formulation design without phase separation issues`.` Recent work from Merck KGaA (`European Journal ` fold)`.
Its ability to form mixed micelles with phospholipids has led to breakthroughs in transdermal insulin patches`.` In vitro diffusion experiments demonstrate % insulin retention across porcine skin models after hours`.
The compound's safety profile is further supported by OECD guideline compliant ecotoxicity tests showing no adverse effects on aquatic organisms at environmentally relevant concentrations`.
Modern analytical techniques like nuclear magnetic resonance (`NMR`) spectroscopy confirm structural integrity even after repeated freeze-thaw cycles`,` critical for lyophilized pharmaceutical preparations`.
Its role as a cosolvent enhancer was validated recently where formulations containing % achieved % permeation enhancement over controls using Franz diffusion cells`.
Researchers have also explored its use as a matrix modifier in electrospun nanofibers`,` improving mechanical strength while maintaining porosity required for tissue engineering scaffolds`.
In cosmetic testing models`,` it reduced TEWL values by % indicating effective barrier function restoration without occlusion-related side effects`.
When combined with polysorbates`,` creates synergistic effects increasing solubility parameters beyond individual components' limits`.
Its application extends into agricultural adjuvants where field trials demonstrated % increase crop foliar uptake efficiency over untreated controls`.
The compound is compatible with both acidic and alkaline environments`,` showing minimal decomposition below pH .
Studies comparing migration rates into food simulants confirm compliance even after months storage at °C .
When used as an additive during nanoparticle synthesis`,` reduces agglomeration tendencies leading better size distribution metrics .
Preclinical toxicology studies show no mutagenicity per Ames test protocols .
It maintains structural integrity under UV exposure making suitable outdoor formulation applications .
Recent advances include covalent attachment onto polymer surfaces creating durable hydrophobic coatings .
Applications span multiple industries including but not limited personal care products medical devices dietary supplements .
Formulations incorporating this ingredient exhibit excellent resistance against shear forces during high-pressure homogenization processes .
When blended with essential oils improves their solubility enabling broader fragrance industry applications .
The molecular weight measured precisely g/mol allows precise stoichiometric calculations during formulation design .
Storage recommendations advise keeping containers sealed away direct sunlight temperatures above °C .
Compliance certifications include ISO , USP , FDA GRAS status ensuring regulatory acceptance across jurisdictions .
Analytical standards available allow accurate quantification via HPLC methods validated per ICH guidelines .
Its low surface tension properties make ideal candidate foaming agents certain industrial cleaning solutions .
Recent patents filed describe novel conjugates combining this surfactant DNA aptamers improving nucleic acid delivery efficiency .
Applications continue evolve including emerging uses cell culture media supplements promoting membrane integrity .
When incorporated into topical creams enhances penetration efficacy without disrupting stratum corneum barrier function .
This concludes our comprehensive overview emphasizing both established uses cutting-edge developments surrounding Sorbitan Trioleate .
Product Overview:
| Product Name: |
Sorbitan Trioleate |
| CAS Number: |
CAS No.?17979-74-7 |
| Molecular Formula: |
C< sub >48H< sub >94O< sub >19 |
| Molecular Weight: |
947 g/mol
|
| Appearance : |
Pale yellow viscous liquid
|
| Melting Point : |
N/A
|
| Boiling Point : |
N/A
|
| Solubility : |
Soluble?in most organic solvents?and?partially soluble?in water.< br />
|
| Storage Conditions : |
Store away from light?at room temperature.< br />
|
| Shelf Life : |
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Key Applications:
- Biomedical Research:& nbsp;Used& nbsp;in& nbsp;formulation&n bsp;of&n bsp;
- Cosmetic Industry:&n bsp;
- Nutritional Supplements:&n bsp;
- P h armaceutical Manufacturing:&nbs p;
- Nano Technology Development:&nbs p;
Safety Information:
Safety Data Sheet:&nbs p;Available upon request
Hazard Class:&nbs p;Non-hazardous material according& nbsp;to& nbsp;
Quality Assurance:
Purity:&nbs p;≥99% HPLC tested
Compliance Standards:&nbs p;USP/NF,&n bsp;
