22:0 Trehalose

For research use only. Not for therapeutic Use.

  • CAT Number: I020777
  • CAS Number: 66758-35-8
  • Molecular Formula: C56H106O13
  • Molecular Weight: 987.45
  • Purity: 98%
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Incorporation of the glycolipid trehalose 6,6'-dibehenate (TDB) into cationic liposomes composed of the quaternary ammonium compound dimethyldioctadecylammonium (DDA) produce an adjuvant system which induces a powerful cell-mediated immune response and a strong antibody response, desirable for a high number of disease targets.


Catalog Number I020777
CAS Number 66758-35-8
Synonyms

22:0 Trehalose; D-(+)-trehalose 6,6'-dibehenate

Molecular Formula C56H106O13
Purity 98%
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,2'R,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-oxybis(3,4,5-trihydroxytetrahydro-2H-pyran-6,2-diyl))bis(methylene) didocosanoate
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 O[C@H]([C@@H](COC(CCCCCCCCCCCCCCCCCCCCC)=O)O[C@H](O[C@@H](O[C@@H]([C@H]([C@@H]1O)O)COC(CCCCCCCCCCCCCCCCCCCCC)=O)[C@@H]1O)[C@@H]2O)[C@@H]2O
Reference

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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.

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