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Merck
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E2271

Sigma-Aldrich

Ectoine

osmoprotectant

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C6H10N2O2
Numero CAS:
96702-03-3
Peso molecolare:
142.16
Beilstein:
7288977
Numero CE:
431-910-1
Numero MDL:
MFCD03419286
Codice UNSPSC:
12352204
ID PubChem:
24894465
NACRES:
NA.25

Livello qualitativo

200

Saggio

≥98.0% (HPLC)
≥98.0% (TLC)

Forma fisica

powder

PM

142.16

Temperatura di conservazione

room temp

Stringa SMILE

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
WQXNXVUDBPYKBA-YFKPBYRVSA-N

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Descrizione generale

Ectoine is a natural cyclic tetrahydropyrimidine, which is a low molecular weight, water-binding and organic osmolyte. It is a part of a class of small molecule chaperones (SMCs).

Azioni biochim/fisiol

Ectoine acts as an osmoprotectant in a wide variety of microorganisms including heterotrophic, halophilic bacteria and non-halophilic bacteria such as Streptomyces species and E.coli. This compatible solute exhibit protective effects in E.coli during drying and storage. Ectoine is implicated in protein and lipid bilayer stabilization. It also regulates the preservation of turgor pressure and ameliorates desiccation stress. It may be used to treat inflammatory diseases such as, allergic rhinitis, atopic dermatitis and chronic obstructive pulmonary disease. Ectoine can cause DNA structural changes in vitro and protects DNA from ionizing radiation (IR). It prevents insulin amyloid formation in vitro.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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Ectoine and hydroxyectoine inhibit aggregation and neurotoxicity of Alzheimer?s beta-amyloid
Kanapathipillai M, et al.
Febs Letters, 579(21), 4775-4780 (2005)
G Malin et al.
Journal of bacteriology, 178(2), 385-395 (1996-01-01)
The metabolic responses of a number of Streptomyces strains to osmotic and heat stress were studied by 13C nuclear magnetic resonance spectroscopy. During cell growth in a chemically defined medium supplemented with 0.5 M NaCl, tetrahydropyrimidine derivatives (THPs), 2-methyl-4-carboxy-5-hydroxy-3,4,5,6-tetrahydropyrimidine [THP(A)]
Biosynthesis of the stress-protectant and chemical chaperon ectoine: biochemistry of the transaminase EctB
Bremer E, et al.
Frontiers in Microbiology, 10, 2811-2811 (2019)
Ectoine-containing cream in the treatment of mild to moderate atopic dermatitis: a randomised, comparator-controlled, intra-individual double-blind, multi-center trial
Marini A, et al.
Skin Pharmacology and Physiology, 27(2), 57-65 (2014)
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.
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