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81619

Sigma-Aldrich

Ectoine

≥95.0% (HPLC)

Sinônimo(s):

(S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid, Thp(B)

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About This Item

Fórmula empírica (Notação de Hill):
C6H10N2O2
Número CAS:
96702-03-3
Peso molecular:
142.16
Beilstein:
7288977
Número CE:
431-910-1
Número MDL:
MFCD03419286
Código UNSPSC:
24112111
ID de substância PubChem:
329769212
NACRES:
NA.21

Nível de qualidade

200

Ensaio

≥95.0% (HPLC)

Formulário

powder

peso molecular

142.16 g/mol

condição de armazenamento

dry at room temperature

cor

white

solubilidade

methanol: soluble 10 mg/mL, clear, colorless to almost colorless

cadeia de caracteres SMILES

CC1=N[C@@H](CCN1)C(O)=O

InChI

1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1

chave InChI

WQXNXVUDBPYKBA-YFKPBYRVSA-N

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Descrição geral

Ectoine, also known as 4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, is a zwitterionic amino acid derivative that is a compatible osmoprotectant solute produced in certain aerobic, chemoheterotrophic, and halophilic bacteria to protect against osmotic stress, radiation, and other unfavorable environmental conditions.

Aplicação

The practical applications of ectoine include enzyme stabilization, anti-inflammatory treatment, neurodegenerative disease prevention, and other therapeutic applications.

Ações bioquímicas/fisiológicas

Ectoine works as an enzyme stabilizer by maintaining hydration and reducing enzyme denaturation due to temperature changes. It also increases the stability of double-stranded DNA at high temperatures.

Outras notas

Stabilizer for enzymes and biological macromolecules

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
BCCH1854
BCCG0908
BCCF8454
BCCF8455
BCCF0707

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Jens Smiatek et al.
Biophysical chemistry, 160(1), 62-68 (2011-10-22)
We have performed Molecular Dynamics simulations of ectoine, hydroxyectoine and urea in explicit solvent. Special attention has been spent on the local surrounding structure of water molecules. Our results indicate that ectoine and hydroxyectoine are able to accumulate more water
K. Lippert, E.A. Galinski
Applied Microbiology and Biotechnology, 37, 61-61 (1992)
Ruediger Graf et al.
Clinics in dermatology, 26(4), 326-333 (2008-08-12)
The protective properties of ectoine, formerly described for only extremophilic microorganisms, can be transferred to human skin. Our present data show that the compatible solute ectoine protects the cellular membrane from damage caused by surfactants. Transepidermal water loss measurements in
Ralf Spindler et al.
Cryobiology, 64(3), 250-260 (2012-02-22)
Cellular response during the freeze-thaw process strongly affects the cryopreservation outcome including cell morphology and cell viability. Cryomicroscopy was used to individually analyze the osmotic response of human pulmonary microvascular endothelial cells (HPMECs) during slow cooling (1 °C/min) to -60
Naomi Ofer et al.
Applied and environmental microbiology, 78(20), 7483-7486 (2012-08-14)
Mycobacterium smegmatis is a commonly used mycobacterial model system. Here, we show that M. smegmatis protects itself against elevated salinity by synthesizing ectoine and hydroxyectoine and characterize the phenotype of a nonproducing mutant. This is the first analysis of M.
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