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E2271

Ectoine

osmoprotectant

Synonym(s):

(S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid, Thp(B)

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Pack SizeSKUAvailabilityPrice
25 mg
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$355.00
100 mg
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$1,130.00

About This Item

Empirical Formula (Hill Notation):
C6H10N2O2
CAS Number:
96702-03-3
Molecular Weight:
142.16
UNSPSC Code:
12352204
NACRES:
NA.25
PubChem Substance ID:
24894465
EC Number:
431-910-1
Beilstein/REAXYS Number:
7288977
MDL number:
MFCD03419286
Assay:
≥-98.0% (HPLC)
Form:
powder
Quality level:
200

$355.00

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Quality Level

200

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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1 of 1

This Item
816190238059570709
Ectoine osmoprotectant

Sigma-Aldrich

E2271

Ectoine

Ectoine ≥95.0% (HPLC)

Sigma-Aldrich

81619

Ectoine

Ectoine primary reference standard

02380595

Ectoine

Hydroxyectoine ≥95% (HPLC)

Sigma-Aldrich

70709

Hydroxyectoine

form

powder

form

powder

form

-

form

solid

assay

≥-98.0% (HPLC)

assay

≥95.0% (HPLC)

assay

-

assay

≥95% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

200

mol wt

142.16

mol wt

142.16 g/mol

mol wt

-

mol wt

-

storage temp.

room temp

storage temp.

-

storage temp.

-

storage temp.

-

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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Certificates of Analysis (COA)

Lot/Batch Number
0000533886
0000521974
0000533886
0000521974
0000473825

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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)
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)
Ulrich Sydlik et al.
The European respiratory journal, 41(2), 433-442 (2012-10-27)
The life span of neutrophilic granulocytes has a determining impact on the intensity and duration of neutrophil driven lung inflammation. Based on the compatible solute ectoine, we aimed to prevent anti-apoptotic reactions in neutrophils triggered by the inflammatory microenvironment in
Jens Smiatek et al.
Biophysical chemistry, 160(1), 62-68 (2011-10-22)
We have performed Molecular Dynamics simulations of ectoine, hydroxyectoine and urea in explicit solvent. Special attention has been spent on the local surrounding structure of water molecules. Our results indicate that ectoine and hydroxyectoine are able to accumulate more water
View All Related Papers

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Global Trade Item Number

SKUGTIN
E2271-100MG04061833619841
E2271-25MG04061833619858

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