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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:
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

Key Documents

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Product Name

Ectoine, osmoprotectant

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

SMILES string

CC1=N[C@@H](CCN1)C(O)=O

assay

≥98.0% (HPLC)
≥98.0% (TLC)

form

powder

mol wt

142.16

storage temp.

room temp

Quality Level

200

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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.

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).

Storage Class

11 - Combustible Solids

wgk

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
0000473825
0000473825
0000453958
0000453958
0000395816

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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)
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)
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)
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)
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