Ectoine

Title: Ectoine
CAS Registry Number: 96702-03-3
CAS Name: (4S)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid
Additional Names: ectoin
Trademarks: RonaCare Ectoin (Merck KGaA)
Molecular Formula: C6H10N2O2
Molecular Weight: 142.16
Percent Composition: C 50.69%, H 7.09%, N 19.71%, O 22.51%
Literature References: Naturally occurring cyclic amino acid. Organic osmolyte; synthesized by microorganisms to maintain osmotic equilibrium in saline environments and to protect enzymes and whole cells from denaturation. Isoln from the halophilic, phototrophic bacterium, Ectothiorhodospira halochloris, and characterization as a compatible solute: E. A. Galinski et al., Eur. J. Biochem. 149, 135 (1985). Biosynthesis: P. Peters et al., FEMS Microbiol. Lett. 71, 157 (1990). Calorimetric analysis of biosynthesis efficiency: T. Maskow, W. Babel, Biochim. Biophys. Acta 1527, 4 (2001). Chromatographic determn: V. Riis et al., Anal. Bioanal. Chem. 377, 203 (2003). Osmoprotection in E. coli: M. Jebbar et al., J. Bacteriol. 174, 5027 (1992). Mechanism of osmoprotection study: idem et al., ibid. 187, 1293 (2005). Enzyme stabilization study: K. Lippert, E. A. Galinski, Appl. Microbiol. Biotechnol. 37, 61 (1992). In vitro prevention of UVA-induced skin damage: J. Buenger, H. Driller, Skin Pharmacol. Physiol. 17, 232 (2004). Inhibition of b-amyloid peptide aggregation and neurotoxicity: M. Kanapathipillai et al., FEBS Lett. 579, 4775 (2005).
Properties: Crystals from water-free methanol. mp ~280°. [a]D20 +140° (c = 1.0 in methanol). Soly at 4°: 6 mol/kg water. Non-ionic character at physiological pH.
Melting point: mp ~280°
Optical Rotation: [a]D20 +140° (c = 1.0 in methanol)
Use: Stabilizer in biotechnological processes; protects the taste of food during dehydration; moisturizer in cosmetics; protects skin against photoaging and formation of sunburn cells.
Ectylurea Eculizumab Edatrexate Edestin Edifenphos

Ectoine[1]
Ectoine structural formulae v.1.png
Identifiers
CAS number 96702-03-3
PubChem 126041
ChemSpider 112069 YesY
UNII 7GXZ3858RY YesY
KEGG C06231 YesY
ChEBI CHEBI:27592 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C6H10N2O2
Molar mass 142.16 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ectoine (1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a compatible solute which serves as a protective substance by acting as an osmolyte and thus helps organisms survive extreme osmotic stress. Ectoine is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism Ectothiorhodospira halochloris, but has since been found in a wide range of gram-negative and gram-positive bacteria. Some other species ectoine was found in:

  • Marinococcus halophilus
  • Pseudomonas stutzeri
  • Halomonas elongata