Trehalose
Trehalose, extracted from Saccharomyces cerevisiae, is a non-reducing sugar formed by an α,α-1,1-glucosidic bond between two α-glucose units, which can be used as a food additive and pharmaceutical excipient. Trehalose is associated with the capacity of stress tolerance in certain types of unicellular and multicellular organisms. For mammalian cells, presence of extra- and intracellular trehalose has been reported to enhance tolerance against desiccation and freezing. However, trehalose must be present on both sides of the cell membrane to confer protection. Due to the non-charged and hydrophilic properties, trehalose is unable to freely penetrate the mammalian cell membrane without external interventions such as acetylation. Using trehalose as a backbone to engineer cell permeable chemicals provides an exciting opportunity for investigating the trehalose potency as an intracellular, nontoxic protective agent in various cell types during biopreservation studies.
References:
1. Megarry AJ, Booth J, Burley J. Amorphous trehalose dihydrate by cryogenic milling. Carbohydrate Research, 2011, 346(8): 1061-1064.
2. Abazari A, Meimetis LG, Budin G, et al. Engineered Trehalose Permeable to Mammalian Cells. PLoS One, 2015, 10(6): e0130323.
Physical Appearance | A solid |
Storage | Store at -20°C |
M.Wt | 342.3 |
Cas No. | 99-20-7 |
Formula | C12H22O11 |
Solubility | ≥34.2 mg/mL in H2O; insoluble in DMSO; insoluble in EtOH |
Chemical Name | (2R,2'R,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-6,6'-oxybis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol) |
SDF | Download SDF |
Canonical SMILES | OC[C@]1([H])[C@](O)([H])[C@@](O)([H])[C@](O)([H])[C@](O[C@]2([H])[C@@](O)([H])[C@](O)([H])[C@@](O)([H])[C@@](O2)([H])CO)([H])O1 |
Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Chemical structure

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