E2271

Ectoine

osmoprotectant

• Synonym(s): (S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid, Thp(B)
• 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: 12352204
• PubChem Substance ID: 24894465
• NACRES: NA.25

Properties

• Quality Level: 200
• Assay: ≥98.0% (HPLC); ≥98.0% (TLC)
• form: powder
• mol wt: 142.16
• storage temp.: room temp
• 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

Description

General description

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).

Biochem/physiol Actions

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.

Safety Information

• 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