Synonym
22:0 Trehalose; D-(+)-trehalose 6,6'-dibehenate
IUPAC/Chemical 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 Key
ZLJJDBSDZSZVTF-LXOQPCSCSA-N
InChi Code
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
SMILES Code
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
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
987.45
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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.
