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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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E2271-25MG

$301.75

E2271-100MG

$1,130.00

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About This Item

Empirical Formula (Hill Notation):
C6H10N2O2
CAS Number:
96702-03-3
Molecular Weight:
142.16
Beilstein/REAXYS Number:
7288977
EC Number:
431-910-1
MDL number:
MFCD03419286
UNSPSC Code:
12352204
PubChem Substance ID:
24894465
NACRES:
NA.25

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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

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1 of 4

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), ≥98.0% (TLC)

assay

≥95.0% (HPLC)

assay

-

assay

≥95% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

200

storage temp.

room temp

storage temp.

-

storage temp.

-

storage temp.

-

mol wt

142.16

mol wt

142.16 g/mol

mol wt

-

mol wt

-

General description

Ectoine is a natural cyclic tetrahydropyrimidine, which is a low molecular weight, water-binding and organic osmolyte.[1] It is a part of a class of small molecule chaperones (SMCs).[2]

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.[3][4] Ectoine is implicated in protein and lipid bilayer stabilization.[5][4] It also regulates the preservation of turgor pressure[5] and ameliorates desiccation stress.[4] It may be used to treat inflammatory diseases such as, allergic rhinitis, atopic dermatitis and chronic obstructive pulmonary disease.[5] Ectoine can cause DNA structural changes in vitro and protects DNA from ionizing radiation (IR).[5] It prevents insulin amyloid formation in vitro.[2]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

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
0000453958
0000453958
0000395816
0000395816
0000244220

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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)
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)
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)
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