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| Targets |
As a glycolipid, 6-O-Oleoyltrehalose is used as an excipient in the formation of lipid nanoparticles (LNPs) for drug delivery. Its primary biochemical role is to act as a non‑ionic surfactant and stabilizing agent. It interacts with lipid bilayers and interfaces, reducing surface tension and preventing the denaturation and aggregation of proteins (like LDH) during freezing and thawing.
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| ln Vitro |
In vitro, 6-O-Oleoyltrehalose is used as a stabilizer to preserve the activity of enzymes such as Lactate Dehydrogenase (LDH) during freeze/thaw cycles. In a typical assay, LDH is mixed with varying concentrations of the trehalose derivative and subjected to several freeze-thaw cycles (e.g., freezing at -80degC and thawing at 37degC). After the cycles, the residual enzymatic activity is measured by following the reduction of NAD+ to NADH at 340 nm. The LDH activity can be preserved by up to 93% in the presence of 1% 6-O-oleoyltrehalose. The compound also demonstrates biodegradable and low surface tension reduction properties.
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| ln Vivo |
In vivo, 6-O-Oleoyltrehalose has been evaluated as a component of topical formulations. In a study using rabbit ear skin with a tape stripping test, lipid nanoparticles (LNPs) containing 6-O-oleoyltrehalose and encapsulating cyclosporin A preferentially accumulated in the stratum corneum rather than in the epidermis and dermis. This indicates its potential for enhancing localized drug delivery to the skin's outer barrier, making it valuable for dermatological research.
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| Enzyme Assay |
Non-cell-based (cell-free) experiments for 6-O-Oleoyltrehalose focus on its physicochemical and stabilizing properties. A typical assay to measure LDH stabilization involves mixing LDH enzyme (e.g., from rabbit muscle) with varying concentrations of 6-O-Oleoyltrehalose (0.01% to 1% w/v) in a phosphate buffer (pH 7.2). The samples are subjected to multiple freeze-thaw cycles (e.g., 3-5 cycles of freezing at -80degC and thawing at 37degC). The residual LDH activity is then measured at 340 nm by adding pyruvate and NADH. The surface activity is measured by a tensiometer using the pendant drop method to calculate the reduction in surface tension.
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| Cell Assay |
Cell-based experiments for 6-O-Oleoyltrehalose are primarily conducted to assess its use in drug delivery systems. For ex vivo studies, lipid nanoparticles (LNPs) containing 6-O-oleoyltrehalose and a fluorescently labeled immunosuppressant (e.g., cyclosporin A) are prepared. In a tape stripping test using rabbit ear skin, the LNP formulation is applied topically. After a designated period (e.g., 4-24 hours), the stratum corneum is removed via adhesive tape, and the fluorescence intensity in the tape strips and residual skin (epidermis and dermis) is measured to quantify drug penetration and accumulation. The results show a preference for accumulation in the stratum corneum compared to deeper skin layers.
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| Animal Protocol |
In vivo animal experiments for 6-O-Oleoyltrehalose are limited. The compound is primarily used ex vivo as a formulation component. The main in vivo applications would be part of a drug delivery study for a therapeutic compound. For example, an LNP formulation containing 6-O-oleoyltrehalose and an active pharmaceutical ingredient (API) might be applied topically to mice or rats. The animal is observed for signs of irritation or efficacy. Standard protocols include measuring skin thickness, performing histology, and analyzing blood levels of the API. The compound is not typically administered systemically.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 6-O-Oleoyltrehalose is not applicable, as it is an excipient and not a therapeutic agent. Its physical properties are well-defined: it has a molecular formula of C30H₅4O12 and a molecular weight of 606.74 g/mol. As a glycolipid, it is biodegradable. It is stored as a solid at -20degC (stable for 3 years) or in a solvent at -80degC. It is soluble in DMSO and organic solvents.
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| Toxicity/Toxicokinetics |
The toxicity of 6-O-Oleoyltrehalose is considered low. As a derivative of the generally recognized as safe (GRAS) disaccharide trehalose, it is expected to have low oral toxicity. However, as a research chemical, standard safety precautions apply: the compound may be harmful if swallowed, inhaled, or absorbed through the skin. It may cause skin and eye irritation. It should be handled in a well-ventilated area (fume hood) with appropriate PPE (lab coat, gloves, safety goggles).
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| References | |
| Additional Infomation |
Additional information: 6-O-Oleoyltrehalose is a white to off-white powder. Its IUPAC name is (2R,3R,4S,5S,6R)-2-[(2S,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol, with an oleoyl group attached at the 6-O position. It is available from chemical suppliers (e.g., Biosynth: NNA73338). It is also known as trehalose monooleate and 6-trehalose monooleate.
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| Molecular Formula |
C30H54O12
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| Molecular Weight |
606.74
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| CAS # |
338733-38-3
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| Appearance |
Typically exists as solids at room temperature
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6482 mL | 8.2408 mL | 16.4815 mL | |
| 5 mM | 0.3296 mL | 1.6482 mL | 3.2963 mL | |
| 10 mM | 0.1648 mL | 0.8241 mL | 1.6482 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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