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30611

Sigma-Aldrich

Trehalose 6-dodecanoate

≥95.0% (GC)

Synonym(s):

α,α-Trehalose 6-laurate, α-D-Glucopyranosyl-α-D-glucopyranoside 6-dodecanoate, 6-O-Lauroyl-α,α-trehalose, Trehalose 6-laurate

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About This Item

Empirical Formula (Hill Notation):
C24H44O12
CAS Number:
64622-91-9
Molecular Weight:
524.60
UNSPSC Code:
12161900
PubChem Substance ID:
329753546
NACRES:
NA.25

assay

≥95.0% (GC)

form

powder

mol wt

524.60 g/mol

technique(s)

protein quantification: suitable

CMC

0.15 mM

storage temp.

2-8°C

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(CCCCCCCCCCC)=O)[C@@H](O)[C@H](O)[C@H]2O

InChI

1S/C24H44O12/c1-2-3-4-5-6-7-8-9-10-11-16(26)33-13-15-18(28)20(30)22(32)24(35-15)36-23-21(31)19(29)17(27)14(12-25)34-23/h14-15,17-25,27-32H,2-13H2,1H3/t14?,15?,17-,18-,19?,20?,21+,22+,23-,24-/m1/s1

Inchi Key

LISGDTVWONGLJR-VOEYTPSHSA-N

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

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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M Woudenberg-van Oosterom et al.
Biotechnology and bioengineering, 49(3), 328-333 (1996-02-05)
The acylation of several disaccharides by ethyl butanoate and ethyl dodecanoate was catalyzed by Candida antarctica lipase in tert-butyl alcohol, at temperatures ranging from 40 degrees to 82 degrees C (reflux temperature). The relative reaction rates of the various disaccharides
T Raku et al.
Journal of biotechnology, 100(3), 203-208 (2002-11-22)
To improve trehalose lipophilicity, trehalose was regioselectively esterified with vinyl fatty acid esters in dimethyl formamide by protease from Bacillus subtilis to give 6-O-lauroyltrehalose, 6-O-myristoyltrehalose, 6-O-palmitoyltrehalose, 6-O-stearoyltrehalose, 6-O-oleoyltrehalose and 6-O-linoleoyltrehalose. The influence of structural variation by changing fatty acid substitute
Lipase-catalyzed esterification of some alpha-D-glucopyranosides in dry media under focused microwave irradiation.
Gelo-Pujic, M., et al.
Journal of the Chemical Society. Perkin Transactions 1, 23, 2777-2278 (1996)
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)
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