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81619

Sigma-Aldrich

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

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
Xiangyang Li et al.
Journal of bacteriology, 194(16), 4473-4474 (2012-07-31)
We present the draft genome sequence of Pseudomonas stutzeri TS44, a moderately halotolerant, arsenite-oxidizing bacterium isolated from arsenic-contaminated soil. The genome contains genes for arsenite oxidation, arsenic resistance, and ectoine/hydroxyectoine biosynthesis. The genome information will be useful for exploring adaptation
Denise Freimark et al.
Cryobiology, 63(2), 67-75 (2011-05-31)
Human mesenchymal stem cells (hMSCs) have great potential for clinical therapy and regenerative medicine. One major challenge concerning their application is the development of an efficient cryopreservation protocol since current methods result in a poor viability and high differentiation rates.
T. Sauer et al.
GIT Labor-Fachzeit., 39, 892-892 (1995)
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

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