81619
Ectoine
≥95.0% (HPLC)
Synonym(s):
(S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid, Thp(B)
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About This Item
Empirical Formula (Hill Notation):
C6H10N2O2
CAS Number:
Molecular Weight:
142.16
Beilstein:
7288977
EC Number:
MDL number:
UNSPSC Code:
24112111
PubChem Substance ID:
NACRES:
NA.21
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Quality Level
Assay
≥95.0% (HPLC)
form
powder
mol wt
142.16 g/mol
storage condition
dry at room temperature
color
white
solubility
methanol: soluble 10 mg/mL, clear, colorless to almost colorless
SMILES string
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
InChI key
WQXNXVUDBPYKBA-YFKPBYRVSA-N
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General description
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.
Biochem/physiol Actions
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.
Other Notes
Stabilizer for enzymes and biological macromolecules
Storage Class Code
11 - Combustible Solids
WGK
WGK 1
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
Rakesh Kumar Harishchandra et al.
Biochimica et biophysica acta, 1808(12), 2830-2840 (2011-09-06)
Ectoine and hydroxyectoine belong to the family of compatible solutes and are among the most abundant osmolytes in nature. These compatible solutes protect biomolecules from extreme conditions and maintain their native function. In the present study, we have investigated the
Lei Cai et al.
Microbial cell factories, 10, 88-88 (2011-11-02)
Halophilic bacteria have shown their significance in industrial production of polyhydroxyalkanoates (PHA) and are gaining more attention for genetic engineering modification. Yet, little information on the genomics and PHA related genes from halophilic bacteria have been disclosed so far. The
Fabrizio Marinelli et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(49), E1285-E1292 (2011-11-16)
Numerous membrane importers rely on accessory water-soluble proteins to capture their substrates. These substrate-binding proteins (SBP) have a strong affinity for their ligands; yet, substrate release onto the low-affinity membrane transporter must occur for uptake to proceed. It is generally
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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