E2271
Ectoine
osmoprotectant
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:
Molecular Weight:
142.16
UNSPSC Code:
12352204
NACRES:
NA.25
PubChem Substance ID:
EC Number:
431-910-1
Beilstein/REAXYS Number:
7288977
MDL number:
Quality Level
assay
≥-98.0% (HPLC)
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
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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.
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)]
Ectoine and hydroxyectoine inhibit aggregation and neurotoxicity of Alzheimer?s beta-amyloid
Kanapathipillai M, et al.
Febs Letters, 579(21), 4775-4780 (2005)
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.
Rakesh Kumar Harishchandra et al.
Biochimica et biophysica acta, 1808(12), 2830-2840 (2011-09-06)
Ectoine and hydroxyectoine belong to the family of compatible solutes and are among the most abundant osmolytes in nature. These compatible solutes protect biomolecules from extreme conditions and maintain their native function. In the present study, we have investigated the
Related Content
Instructions
Global Trade Item Number
| SKU | GTIN |
|---|---|
| E2271-100MG | 04061833619841 |
| E2271-25MG | 04061833619858 |
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