ECTOINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H10N2O2
Molecular Weight	142.1558
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NCC[C@H](N1)C(O)=O

InChI

InChIKey=WQXNXVUDBPYKBA-YFKPBYRVSA-N

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

HIDE SMILES / InChI

Molecular Formula	C6H10N2O2
Molecular Weight	142.1558
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.sigmaaldrich.com/catalog/product/sigma/e2271 | https://www.ncbi.nlm.nih.gov/pubmed/8071195 | https://www.degruyter.com/downloadpdf/j/aiht.2016.67.issue-4/aiht-2016-67-2837/aiht-2016-67-2837.pdf

Ectoine is a natural compound found in several species of bacteria, including heterotrophic, halophilic bacteria and non-halophilic bacteria such as Streptomyces species and E.coli. It serves as an osmoprotectant, protecting microorganisms from high concentrations of salts. Ectoine is used as a protective agent for E.Coli during drying and storage. In the cosmetic and drug industry, ectoine is used as an active ingredient in skin care and sun protection products, working by stabilization proteins and other cellular structures. Ectoine has a number of applications in medicine: it alleviates inflammation reactions, protects cells from damage during cryopreservation, protects against neurodegenerative diseases and from against ischemia and reperfusion injury. Ectoine-containing formulations are investigated in the clinical trials for the treatment of allergic rhinitis and conjunctivitis, atopic dermatitis, asthma, and other conditions.

Approval Year

PubMed

Title	Date	PubMed
Responses of a novel salt-tolerant Streptomyces albidoflavus DUT_AHX capable of degrading nitrobenzene to salinity stress.	2009-02	18516688
Cloning and heterologous expression of ectoine biosynthesis genes from Bacillus halodurans in Escherichia coli.	2008-08	18488150
Compatible solute influence on nucleic acids: many questions but few answers.	2008-06-03	18522725
Cloning and characterization of the gene cluster for biosynthesis of ectoine from Nesterenkonia halobia DSM 20541.	2008-06	18604501
Characterization of the recombinant diaminobutyric acid acetyltransferase from Methylophaga thalassica and Methylophaga alcalica.	2008-06	18410346
Influence of salts and pH on growth and activity of a novel facultatively alkaliphilic, extremely salt-tolerant, obligately chemolithoautotrophic sufur-oxidizing Gammaproteobacterium Thioalkalibacter halophilus gen. nov., sp. nov. from South-Western Siberian soda lakes.	2008-05	18309455
Regulation of osmoadaptation in the moderate halophile Halobacillus halophilus: chloride, glutamate and switching osmolyte strategies.	2008-04-28	18442383
Genotoxicity of visible light (400-800 nm) and photoprotection assessment of ectoin, L-ergothioneine and mannitol and four sunscreens.	2008-04-25	18325778
Microbial life at high salt concentrations: phylogenetic and metabolic diversity.	2008-04-15	18412960
Proteomics with a pinch of salt: a cyanobacterial perspective.	2008-04-15	18412952
Efficient cyclic system to yield ectoine using Brevibacterium sp. JCM 6894 subjected to osmotic downshock.	2008-03-01	17696218
[Cloning and characterization of ectABC cluster from Bacillus alcalophilus DTY1].	2008-03	18589814
Growth phase-dependent switch in osmolyte strategy in a moderate halophile: ectoine is a minor osmolyte but major stationary phase solute in Halobacillus halophilus.	2008-03	18093162
Small stress molecules inhibit aggregation and neurotoxicity of prion peptide 106-126.	2008-01-25	18039468
Crystal structure of the ligand-binding protein EhuB from Sinorhizobium meliloti reveals substrate recognition of the compatible solutes ectoine and hydroxyectoine.	2007-12-14	17996893
[Osmoadaptation of haloalkaliphilic bacteria: role of osmoregulators and their possible practical application].	2007-12-12	18069317
Compatible solutes from hyperthermophiles improve the quality of DNA microarrays.	2007-11-23	18036223
Ectoine as a natural component of food: detection in red smear cheeses.	2007-11	17961287
Halomonas sinaiensis sp. nov., a novel halophilic bacterium isolated from a salt lake inside Ras Muhammad Park, Egypt.	2007-11	17618404
Osmotically induced synthesis of the compatible solute hydroxyectoine is mediated by an evolutionarily conserved ectoine hydroxylase.	2007-10-26	17636255
[Study progress on compatible solutes in moderately halophilic bacteria].	2007-10	18062278
Response of Halomonas campisalis to saline stress: changes in growth kinetics, compatible solute production and membrane phospholipid fatty acid composition.	2007-09	17651393
Characterization of compatible solute transporter multiplicity in Corynebacterium glutamicum.	2007-09	17390131
Microscopic understanding of preferential exclusion of compatible solute ectoine: direct interaction and hydration alteration.	2007-08-30	17676787
[Moderately haloalkaliphilic aerobic methylobacteria].	2007-07-19	17633404
Relative importance of amino acids, glycine-betaine and ectoine synthesis in the biocontrol agent Pantoea agglomerans CPA-2 in response to osmotic, acidic and heat stress.	2007-07	17594453
In vivo skin antioxidant effect of a new combination based on a specific Vitis vinifera shoot extract and a biotechnological extract.	2007-06	17691204
[Detection of osmoprotector ectoine content in methylotrophic bacteria using of normal-phase high performance liquid chromatography].	2007-05-05	17476809
[Characterization of the ectC gene and its expression product in Halomonas sp. Nj223 from Antarctica deep-sea sediment].	2007-04	17552251
Crystal structures of an Extracytoplasmic Solute Receptor from a TRAP transporter in its open and closed forms reveal a helix-swapped dimer requiring a cation for alpha-keto acid binding.	2007-03-15	17362499
The role of LRP and H-NS in transcription regulation: involvement of synergism, allostery and macromolecular crowding.	2007-02-23	17196617
Halomonas alkaliantarctica sp. nov., isolated from saline lake Cape Russell in Antarctica, an alkalophilic moderately halophilic, exopolysaccharide-producing bacterium.	2007-01	16621401
In vivo assessment of Ectoin: a randomized, vehicle-controlled clinical trial.	2007	17519560
[Identification of moderately halophilic strain DTY1 and study of its halotolerant mechanism].	2006-12	17302161
Supplementation effect of ectoine on thermostability of phytase.	2006-12	17270722
Osmoprotection of Salmonella enterica serovar Typhimurium by Ngamma-acetyldiaminobutyrate, the precursor of the compatible solute ectoine.	2006-12	16469465
Transport kinetics of ectoine, an osmolyte produced by Brevibacterium epidermis.	2006-11	16900330
Isolation and synthesis of (-)-(5S)-2-imino-1-methylpyrrolidine-5- carboxylic acid from Cliona tenuis: structure revision of pyrostatins.	2006-10-12	17020348
The evaluation of the factors that cause aggregation during recombinant expression in E. coli is simplified by the employment of an aggregation-sensitive reporter.	2006-09-01	16948849
Cloning and characterization of the genes for biosynthesis of the compatible solute ectoine in the moderately halophilic bacterium Halobacillus dabanensis D-8(T).	2006-09	16874550
High-yield cultivation of Marinococcus M52 for production and recovery of hydroxyectoine.	2006-09	16815686
NhaD type sodium/proton-antiporter of Halomonas elongata: a salt stress response mechanism in marine habitats?	2006-07-27	16872527
Compatible solutes as protectants for zymogens against proteolysis.	2006-07	16797260
Succinate-mediated catabolite repression control on the production of glycine betaine catabolic enzymes in Pseudomonas aeruginosa PAO1 under low and elevated salinities.	2006-05	16622056
Characterization of salt tolerance in ectoine-transformed tobacco plants (Nicotiana tabaccum): photosynthesis, osmotic adjustment, and nitrogen partitioning.	2006-02	17080633
[Cloning of the ectoine biosynthesis gene ectABC from Halomonas sp. BYS-1 and salt stressed expression in Escherichia coli].	2006-02	16579460
Supplementation effects of hydroxyectoine on proline uptake of downshocked Brevibacterium sp. JCM 6894.	2006-02	16569616
Effect of duration of osmotic downshock and coexisting glutamate on survival and uptake of ectoine in halotolerant Brevibacterium sp. JCM 6894.	2006-01	16503292
Ectoines as compatible solutes and carbon and energy sources for the halophilic bacterium Chromohalobacter salexigens.	2006	16405689
[Isolation and characteristic of a moderately halophilic bacterium accumulated ectoine as main compatible solute].	2005-12	16496700

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:28:02 GMT 2025` Edited by `admin` on `Mon Mar 31 19:28:02 GMT 2025`
Record UNII	7GXZ3858RY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ECTOINE

Common Name

English

ECTOIN

Preferred Name

English

(4S)-3,4,5,6-TETRAHYDRO-2-METHYL-4-PYRIMIDINECARBOXYLIC ACID

Systematic Name

English

Ectoine [WHO-DD]

Common Name

English

NSC-614616

Code

English

ECTOINE [MI]

Common Name

English

Code System Code Type Description

CAS

96702-03-3