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81619

Sigma-Aldrich

Ectoine

≥95.0% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C6H10N2O2
Numéro CAS:
96702-03-3
Poids moléculaire :
142.16
Numéro Beilstein :
7288977
Numéro CE :
431-910-1
Numéro MDL:
MFCD03419286
Code UNSPSC :
24112111
ID de substance PubChem :
329769212
Nomenclature NACRES :
NA.21

Niveau de qualité

200

Pureté

≥95.0% (HPLC)

Forme

powder

Poids mol.

142.16 g/mol

Conditions de stockage

dry at room temperature

Couleur

white

Solubilité

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

Chaîne 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

Clé InChI

WQXNXVUDBPYKBA-YFKPBYRVSA-N

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Description générale

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.

Application

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

Actions biochimiques/physiologiques

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.

Autres remarques

Stabilizer for enzymes and biological macromolecules

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BCCM0586
BCCM5363
BCCL5220
BCCH1854
BCCJ4305

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Adam Bownik et al.
Arhiv za higijenu rada i toksikologiju, 67(4), 260-265 (2016-12-30)
Ectoine is a compatible water molecule-binding solute (osmoprotectant) produced by several bacterial species in response to osmotic stress and unfavourable environmental conditions. This amino acid derivative can accumulate inside cells at high concentrations without interfering with natural processes and can
Ulrich Sydlik et al.
The European respiratory journal, 41(2), 433-442 (2012-10-27)
The life span of neutrophilic granulocytes has a determining impact on the intensity and duration of neutrophil driven lung inflammation. Based on the compatible solute ectoine, we aimed to prevent anti-apoptotic reactions in neutrophils triggered by the inflammatory microenvironment in
Alexander S Reshetnikov et al.
Extremophiles : life under extreme conditions, 15(6), 653-663 (2011-10-06)
The genes of ectoine biosynthesis pathway were identified in six species of aerobic, slightly halophilic bacteria utilizing methane, methanol or methylamine. Two types of ectoine gene cluster organization were revealed in the methylotrophs. The gene cluster ectABC coding for diaminobutyric
M.D. Vangala et al.
Bioforum, 23, 760-760 (2000)
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
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