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T0167

D-(+)-Trehalose dihydrate

Name: <SC>D</SC>-(+)-Trehalose dihydrate
Brand: SIGMA

from Saccharomyces cerevisiae, powder, BioReagent, suitable for cell culture, suitable for insect cell culture, ≥99%

Synonym(s):

α,α-Trehalose, α-D-Glucopyranosyl-α-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₂₂O₁₁ · 2H₂O

CAS Number:

6138-23-4

Molecular Weight:

378.33

UNSPSC Code:

12352201

NACRES:

NA.75

PubChem Substance ID:

24899871

EC Number:

202-739-6

Beilstein/REAXYS Number:

5322018

MDL number:

MFCD00071594

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Properties

Quality Level

200

biological source

Saccharomyces cerevisiae

product line

BioReagent

assay

≥99%

form

powder

technique(s)

cell culture | insect: suitable, cell culture | mammalian: suitable

solubility

H₂O: 50 mg/mL

SMILES string

[H]O[H].[H]O[H].OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C12H22O11.2H2O/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12;;/h3-20H,1-2H2;2*1H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-;;/m1../s1

InChI key

DPVHGFAJLZWDOC-PVXXTIHASA-N

Description

General description

Trehalose is a non-reducing disaccharide, ubiquitously present in nature. It is used as a food preservative and also to retain enzymes, vaccines, cells and many other molecules. Trehalose is present as hemolymph sugar among the invertebrates.

Application

D-(+)-Trehalose dihydrate has been used in a slow-freezing method for freezing rabbit oocytes. It has also been used in solid-surface vitrification (SSV) of in vitro-matured oocytes. It is suitable for use as a cryoprotectant in a variety of cell freezing media.

Biochem/physiol Actions

Trehalose is essential for embryogenesis, carbon metabolism, photosynthesis and flowering in plants. It predominantly exists among the species that supports anhydrobiosis (life without water). It serves as a carbohydrate reserve in microorganisms and protects them from adverse conditions, such as heat, cold, dehydration, desiccation and oxidation. Trehalose acts as a chemical chaperone affecting protein folding. It is known to prevent amyloid generation and accummulation of β-amyloid in vitro. A similar effect of trehalose has been observed with huntingtin protein aggregation. Thus, it might serve as a protective agent in Alzheimer′s disease and Huntington′s disease.

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Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Production of good-quality porcine blastocysts by in vitro fertilization of follicular oocytes vitrified at the germinal vesicle stage

Somfai T, et al.

Theriogenology, 73, 147-156 (2010)

Trehalose metabolism: from osmoprotection to signaling

Iturriaga G, et al.

International Journal of Molecular Sciences, 10(9), 3793-3810 (2009)

Developmental competence of in vitro-fertilized porcine oocytes after in vitro maturation and solid surface vitrification: effect of cryopreservation on oocyte antioxidative system and cell cycle stage