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

Quality Level

200

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

81619-1G-F:
81619-10G-F:
81619-100G-F:
81619-VAR-F:
81619-BULK-F:

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Certificates of Analysis (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
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
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.
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
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