Ectoine

Bezeichnung:Ectoine

CAS-Nr96702-03-3

Englisch Name:Ectoine

CBNumberCB4359836

SummenformelC6H10N2O2

Molgewicht142.16

MOL-Datei96702-03-3.mol

Ectoine physikalisch-chemischer Eigenschaften

Schmelzpunkt	~280°
alpha	D20 +140° (c = 1.0 in methanol)
Siedepunkt	381.5±35.0 °C(Predicted)
Dichte	1.37
storage temp.	2-8°C
Löslichkeit	methanol: 20 mg/mL, clear, colorless
pka	3.14±0.20(Predicted)
Aggregatzustand	Solid
Farbe	White to Off-White
Wasserlöslichkeit	Water : 250 mg/mL (1758.58 mM)
BRN	7288977
Stabilität	Hygroscopic
InChI	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
InChIKey	WQXNXVUDBPYKBA-YFKPBYRVSA-N
SMILES	C1(C)=NCC[C@@H](C(O)=O)N1

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	1
HS Code	2933.59.9500

Ectoine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Ectoine is a cyclic tetrahydropyrimidine organic osmolyte, which was discovered in the halophilic bacterium Ectothiorhodospira halochloris. It is the most abundant solute produced by aerobic heterotrophic eubacteria and has been extensively characterized as an osmoprotectant and stabilizer for cells and biomolecules.
Ectoine is considered a member of the small molecule chaperones family (SMCs). SMCs accumulate to high intracellular concentrations, preventing the misfolding/ denaturation of proteins and other labile macromolecules. Ectoine preserves enzymes and whole cells against harmful conditions such as freezing, drying, or heating. This molecule, among other compatible solutes, possesses the ability to conserve the proteolytic activity of trypsin and chymotrypsin. It has been shown to induce heat shock proteins and downregulate proinflammatory signals in human keratinocytes. It is not toxic to the cellular environment, even at concentrations as high as 100 mM.
Ectoine strongly inhibits the Ab42 amyloid formation in vitro, reducing the toxicity to human neurblastoma cells. Ab42 was found to be the most predominant proteolytic fragment found in amyloid plaques, thus, ectoine may act as a potential inhibitor associated with neurodegenerative diseases.
Verwenden
Ectoine is a natural protector that stabilizes proteins and other cell structures and protects the skin from stresses such as UV exposure and dryness.
Definition
Ectoine is a carboxamidine heterocycle obtained by formal condensation of (2S)-2,4-diaminobutanoic acid with acetic acid. It has a role as an osmolyte. It is a carboxamidine, a member of 1,4,5,6-tetrahydropyrimidines and a monocarboxylic acid. It is a conjugate acid of an ectoinate. It is a tautomer of an ectoine zwitterion.
Biochem/physiol Actions
Ectoine is an osmoprotectant in a variety of microorganisms, including heterotrophic, halophilic and non-halophilic bacteria, such as Streptomyces and E. coli. This compatible solute is also protective for E. coli during drying and storage. Ecdysone is associated with the stabilization of protein and lipid bilayers. It also regulates the retention of bulking pressure and reduces desiccation stress. It can be used in the treatment of inflammatory diseases such as allergic rhinitis, atopic dermatitis and chronic obstructive pulmonary disease. Ecdysone causes structural changes in DNA in vitro and protects DNA from ionizing radiation (IR). It prevents the formation of insulin amyloid in vitro.Ecdysone is an osmoprotectant in a variety of microorganisms, including heterotrophic, halophilic and non-halophilic bacteria, such as Streptomyces and E. coli. This compatible solute is also protective for E. coli during drying and storage. Ecdysone is associated with the stabilization of protein and lipid bilayers. It also regulates the retention of bulking pressure and reduces desiccation stress. It can be used in the treatment of inflammatory diseases such as allergic rhinitis, atopic dermatitis and chronic obstructive pulmonary disease. Ecdysone causes structural changes in DNA in vitro and protects DNA from ionizing radiation (IR). It prevents the formation of insulin amyloid in vitro.
Einzelnachweise
1. Galinski, E.A., et al., 1,4,5,6-Tetrahydro-2-methyl-4- pyrimidinecarboxylic acid. A novel cyclic amino acid from halophilic phototrophic bacteria of the genus Ectothiorhodospira. Eur. J. Biochem., 149, 135 - 139 (1985).
2. Kanapathipillai, M. et al., Ectoine and hydroxyectoine inhibit aggregation and neurotoxicity of Alzheimer’s b-amyloid. FEBS Letters, 579, 4775- 4780 (2005).
3. Kolp, S. et al., Compatible solutes as protectants for zymogens against proteolysis. Biochim. Biophys. Acta, 1764, 1234-1242 (2006).
4. Buommino, E. et al., Ectoine from halophilic microorganisms induces the expression of hsp70 and hsp70B′ in human keratinocytes modulating the proinflammatory response. Cell stress & chap., 10, 197-203 (2005).

Ectoine Upstream-Materialien And Downstream Produkte

Ectoine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

96702-03-3, Ectoine Verwandte Suche:

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