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Merck
CN

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:
Assay:
≥-98.0% (HPLC)
Form:
powder
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Quality Segment

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

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.


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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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Global Trade Item Number

SKUGTIN
E2271-100MG04061833619841
E2271-25MG04061833619858