22:0 Trehalose

• CAT Number: I020777
• CAS Number: 66758-35-8
• Molecular Formula: C56H106O13
• Molecular Weight: 987.45
• Purity: 98%
• Synonyms: 22:0 Trehalose; D-(+)-trehalose 6,6'-dibehenate
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-(docosanoyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl docosanoate
• InChI: InChI=1S/C56H106O13/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-47(57)65-43-45-49(59)51(61)53(63)55(67-45)69-56-54(64)52(62)50(60)46(68-56)44-66-48(58)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h45-46,49-56,59-64H,3-44H2,1-2H3/t45-,46-,49-,50-,51+,52+,53-,54-,55-,56-/m1/s1
• InChIKey: ZLJJDBSDZSZVTF-LXOQPCSCSA-N
• SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)CCCCCCCCCCCCCCCCCCCCC)O)O)O)O)O)O

22:0 Trehalose（Cat No.:I020777）is a modified form of trehalose, a disaccharide sugar composed of two glucose molecules. In this case, 22:0 refers to the fatty acid chain attached to the trehalose molecule, specifically a 22-carbon saturated fatty acid. This modification can enhance the compound’s properties, such as solubility, stability, or biological activity. 22:0 Trehalose has potential applications in drug delivery systems, cosmetics, and biotechnology. Its unique structure may improve its interaction with cell membranes or help protect sensitive compounds, though further research is needed to fully explore its industrial and therapeutic uses.

Reference

1: Cejka C, Kubinova S, Cejkova J. Trehalose in ophthalmology. Histol Histopathol. 2019 Jun;34(6):611-618. doi: 10.14670/HH-18-082. Epub 2019 Jan 9. PMID: 30623968.
2: Lee HJ, Yoon YS, Lee SJ. Mechanism of neuroprotection by trehalose: controversy surrounding autophagy induction. Cell Death Dis. 2018 Jun 15;9(7):712. doi: 10.1038/s41419-018-0749-9. PMID: 29907758; PMCID: PMC6003909.
3: Zhang Y, DeBosch BJ. Using trehalose to prevent and treat metabolic function: effectiveness and mechanisms. Curr Opin Clin Nutr Metab Care. 2019 Jul;22(4):303-310. doi: 10.1097/MCO.0000000000000568. PMID: 31033580.
4: Soper AK, Ricci MA, Bruni F, Rhys NH, McLain SE. Trehalose in Water Revisited. J Phys Chem B. 2018 Jul 26;122(29):7365-7374. doi: 10.1021/acs.jpcb.8b03450. Epub 2018 Jul 17. PMID: 29965765.
5: Jana S , Kulkarni SS . Synthesis of trehalose glycolipids. Org Biomol Chem. 2020 Mar 18;18(11):2013-2037. doi: 10.1039/d0ob00041h. PMID: 32115587.
6: Walmagh M, Zhao R, Desmet T. Trehalose Analogues: Latest Insights in Properties and Biocatalytic Production. Int J Mol Sci. 2015 Jun 15;16(6):13729-45. doi: 10.3390/ijms160613729. PMID: 26084050; PMCID: PMC4490520.
7: Bragg JT, D’Ambrosio HK, Smith TJ, Gorka CA, Khan FA, Rose JT, Rouff AJ, Fu TS, Bisnett BJ, Boyce M, Khetan S, Paulick MG. Esterified Trehalose Analogues Protect Mammalian Cells from Heat Shock. Chembiochem. 2017 Sep 19;18(18):1863-1870. doi: 10.1002/cbic.201700302. Epub 2017 Aug 18. PMID: 28722776.
8: Lee J, Ko JH, Mansfield KM, Nauka PC, Bat E, Maynard HD. Glucose-Responsive Trehalose Hydrogel for Insulin Stabilization and Delivery. Macromol Biosci. 2018 May;18(5):e1700372. doi: 10.1002/mabi.201700372. Epub 2018 Apr 17. PMID: 29665232; PMCID: PMC5986559.
9: Eleutherio E, Panek A, De Mesquita JF, Trevisol E, Magalhães R. Revisiting yeast trehalose metabolism. Curr Genet. 2015 Aug;61(3):263-74. doi: 10.1007/s00294-014-0450-1. Epub 2014 Sep 11. PMID: 25209979.
10: Sakhaee N, Sakhaee S, Takallou A, Mobaraki A, Maddah M, Moshrefi R. Hydrodynamic volume of trehalose and its water uptake mechanism. Biophys Chem. 2019 Jun;249:106145. doi: 10.1016/j.bpc.2019.03.002. Epub 2019 Apr 2. PMID: 30959240.