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Merck
CN

30564

Trehalose 6-hexadecanoate

≥95.0% (GC)

Synonym(s):

α,α-Trehalose 6-palmitate, α-D-Glucopyranosyl-α-D-glucopyranoside 6-hexadecanoate, 6-O-Palmitoyl-α,α-trehalose, Trehalose 6-palmitate

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About This Item

Empirical Formula (Hill Notation):
C28H52O12
CAS Number:
42939-93-5
Molecular Weight:
580.71
UNSPSC Code:
12161900
PubChem Substance ID:
329753539
NACRES:
NA.25

Key Documents

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SMILES string

O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]2O[C@H](COC(CCCCCCCCCCCCCCC)=O)[C@@H](O)[C@H](O)[C@H]2O

InChI

1S/C28H52O12/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(30)37-17-19-22(32)24(34)26(36)28(39-19)40-27-25(35)23(33)21(31)18(16-29)38-27/h18-19,21-29,31-36H,2-17H2,1H3/t18?,19?,21-,22-,23?,24?,25+,26+,27-,28-/m1/s1

InChI key

VNHFMAKRYDWMAF-DHFWNHDGSA-N

assay

≥95.0% (GC)

form

powder

mol wt

580.71 g/mol

CMC

0.0061 mM

storage temp.

2-8°C

Application

Trehalose is commonly used as a stabilizer and protective material for biomaterial compounds. Because of these characteristics, Trehalose is introduced as a hydrophilic part. Due to these properties of Trehalose, protein degeneration is expected to be prevented with Trehalose detergents. Therefore, Trehalose detergents may keep the function of the protein and be utilized in the field of proteomics research.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH2298
BCCF8351
BCBV5767
BCBR6784V
BCBQ2455V

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Nawal K Paul et al.
The Journal of organic chemistry, 78(2), 363-369 (2012-12-12)
It was shown that reaction of trehalose with 1 equiv of a fatty acid in pyridine promoted by 1 equiv of the uronium-based coupling agent 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) at room temperature gives a good yield of the primary ester accompanied
A K Datta et al.
Carbohydrate research, 218, 95-109 (1991-09-30)
A simplified synthesis of 6-mono- and 6,6'-di-corynomycolate esters of alpha,alpha-trehalose, and related compounds, was achieved by coupling the (hydroxyl-protected) acids to the partially trimethylsilylated sugar in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine. As acid reactants, (2-RS,3-RS)-3-hydroxy-2-tetradecyloctadecanoic acid (DL-corynomycolic acid) and
L Schiefelbein et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 76(3), 342-350 (2010-09-08)
Nonionic polyethylene glycol-derived surfactants are today's choice as surfactants in protein formulations. Different groups discovered that although surface-induced stresses are reduced by these excipients, the long-term stability of different proteins decreased due to polyethylene glycol-related induction of oxidation processes under
Chemical and biochemical studies on carbohydrate esters. V. Anti Ehrlich ascites tumor effect and chromatographic behaviors of fatty acyl monoesters of sucrose and trehalose.
Y Nishikawa et al.
Chemical & pharmaceutical bulletin, 25(7), 1717-1724 (1977-07-01)
Surface activities of monoacyl trehaloses in aqueous solution.
Chen, J., et al.
Food Sci. Technol., 40, 412-417 (2006)

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