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
Beilstein:
7288977
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.25
Quality Level
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
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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 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
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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)
Isolation and Synthesis of (-)-(5 S)-2-Imino-1-methylpyrrolidine-5-carboxylic Acid from Cliona t enuis: Structure Revision of Pyrostatins
Castellanos L, et al.
Organic Letters, 8(21) (2006)
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)]
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