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Merck
CN

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:
96702-03-3
Molecular Weight:
142.16
UNSPSC Code:
24112111
NACRES:
NA.21
PubChem Substance ID:
329769212
EC Number:
431-910-1
Beilstein/REAXYS Number:
7288977
MDL number:
MFCD03419286

Key Documents

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Product Name

Ectoine, ≥95.0% (HPLC)

InChI key

WQXNXVUDBPYKBA-YFKPBYRVSA-N

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

SMILES string

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

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

Quality Level

200

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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.

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.

Other Notes

Stabilizer for enzymes and biological macromolecules

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN2331
BCCM0586
BCCM5363
BCCL5220
BCCH1854

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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
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
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
M.D. Vangala et al.
Bioforum, 23, 760-760 (2000)
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
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