| Field | Specification |
|---|---|
| Target | |
| Alternative names | Glucopyranosyl lipid A |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C96H184N3O22P |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Monophosphoryl lipid A, also known as Glucopyranosyl lipid A, is a toll-like receptor 4 agonist derived from the cell wall of nonpathogenic Salmonella. It can be used in immunization and vaccine research[1]. It is supplied as a white to off-white solid (C96H184N3O22P, MW 1763.47) at 99.87% purity.
Physical & Chemical Properties
| CAS Number | 1246298-63-4 |
|---|---|
| Molecular Formula | C96H184N3O22P |
| Molecular Weight | 1763.47 g/mol |
| Purity | 99.87% |
| Appearance | Solid |
| Color | White to off-white |
| SMILES | CCCCCCCCCCCCCC(O[C@@H](CC(N[C@@H]1[C@@H](OC(C[C@H](OC(CCCCCCCCCCCCC)=O)CCCCCCCCCCC)=O)[C@H](OP(O)([O-])=O)[C@@H](CO)O[C@H]1OC[C@@H]2[C@@H](O)[C@H](OC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H](NC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H](O)O2)=O)CCCCCCCCCCC)=O.[NH4+] |
| Target | TLR4 |
| Signaling Pathway | Immunology/Inflammation |
| Solubility | In Vitro: DMSO: 25 mg/mL (14.18 mM; Requires sonication and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | -20°C, sealed storage, away from moisture. In solvent: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 25 mg/mL (14.18 mM) | requires sonication and warming and heat to 60°C; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); sealed storage, away from moisture; avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 90% Corn Oil |
|---|---|
| Result | 2.5 mg/mL (1.42 mM); suspension; requires sonication |
| How to prepare | Gives a suspension at 2.5 mg/mL. The suspension is suitable for oral and intraperitoneal dosing. For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 900 μL corn oil. |
Data provided by the manufacturer.
In Vitro
In dendritic cells, Monophosphoryl lipid A (100 μg/ml, 2 hours) activates NF-κB and modulates TLR2[2]. Monophosphoryl lipid A (24 hours; 5~100 μg/ml; dendritic cells) drives IL-12 production by human cells[2]. Raising the amount of Monophosphoryl lipid A from 0.1 to 1 μg also increases the percentage of matured BMDCs[1]. Monophosphoryl lipid A up-regulates dendritic cell surface markers and enhances T cell responses. In CD4 T cells, Monophosphoryl lipid A increases calcium mobilization of activated T cells[2].
Western Blot Analysis[2]
| Cell Line | Dendritic cells |
|---|---|
| Concentration | 100 μg/ml |
| Incubation Time | 2 hours |
| Result | Induced NF-κB activation and modulated TLR2. |
In Vivo
In mice, the generated Monophosphoryl lipid A has been demonstrated to activate APC and to boost both Th1- and Th2-specific immune responses[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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