U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ECTOINE

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

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

PubMed

TitleDatePubMed
Calorimetrically obtained information about the efficiency of ectoine synthesis from glucose in Halomonas elongata.
2001 Jul 2
Metabolic engineering of osmoprotectant accumulation in plants.
2002 Jan
Comparative study of the thermostabilizing properties of mannosylglycerate and other compatible solutes on model enzymes.
2002 Jun
The substrate-binding protein TeaA of the osmoregulated ectoine transporter TeaABC from Halomonas elongata: purification and characterization of recombinant TeaA.
2002 Jun 4
[The biology and osmoadaptation of haloalkaliphilic methanotrophs].
2002 Mar-Apr
Dynamics and optimal conditions of intracellular ectoine accumulation in Brevibacterium sp.
2003
Glucose 6-phosphate dehydrogenase is required for sucrose and trehalose to be efficient osmoprotectants in Sinorhizobium meliloti.
2003 Dec 12
Potential osmoprotectants for the lactic acid bacteria Pediococcus pentosaceus and Tetragenococcus halophila.
2003 Jul 15
Isolation and characterization of ButA, a secondary glycine betaine transport system operating in Tetragenococcus halophila.
2003 Oct
Impact of transport processes in the osmotic response of Corynebacterium glutamicum.
2003 Sep 4
Carbon and energy fluxes during haloadaptation of Halomonas sp. EF11 growing on phenol.
2004 Apr
Inhibition of insulin amyloid formation by small stress molecules.
2004 Apr 23
Rapid and sensitive NMR method for osmolyte determination.
2004 Aug
Comparative phylogenetic analyses of Halomonas variabilis and related organisms based on 16S rRNA, gyrB and ectBC gene sequences.
2004 May
Ectoine accumulation in Brevibacterium epidermis.
2004 Oct
Ectoine and hydroxyectoine inhibit aggregation and neurotoxicity of Alzheimer's beta-amyloid.
2005 Aug 29
Organic compatible solutes of halotolerant and halophilic microorganisms.
2005 Aug 4
Ectoine from halophilic microorganisms induces the expression of hsp70 and hsp70B' in human keratinocytes modulating the proinflammatory response.
2005 Autumn
[Isolation and characteristic of a moderately halophilic bacterium accumulated ectoine as main compatible solute].
2005 Dec
Fatty acid, compatible solute and pigment composition of obligately chemolithoautotrophic alkaliphilic sulfur-oxidizing bacteria from soda lakes.
2005 Feb 1
[Methylophaga murata sp. nov.: a haloalkaliphilic aerobic methylotroph from deteriorating marble].
2005 Jul-Aug
Ectoine alters subcellular localization of inclusions and reduces apoptotic cell death induced by the truncated Machado-Joseph disease gene product with an expanded polyglutamine stretch.
2005 Oct
Halomonas campaniensis sp. nov., a haloalkaliphilic bacterium isolated from a mineral pool of Campania Region, Italy.
2005 Sep
Ultraviolet A-induced signaling involves a ceramide-mediated autocrine loop leading to ceramide de novo synthesis.
2005 Sep
[Biotechnological potential of methylotrophic bacteria: a review of current status and future prospects].
2005 Sep-Oct
Ectoines as compatible solutes and carbon and energy sources for the halophilic bacterium Chromohalobacter salexigens.
2006
[Identification of moderately halophilic strain DTY1 and study of its halotolerant mechanism].
2006 Dec
Osmoprotection of Salmonella enterica serovar Typhimurium by Ngamma-acetyldiaminobutyrate, the precursor of the compatible solute ectoine.
2006 Dec
[Cloning of the ectoine biosynthesis gene ectABC from Halomonas sp. BYS-1 and salt stressed expression in Escherichia coli].
2006 Feb
Compatible solutes as protectants for zymogens against proteolysis.
2006 Jul
Succinate-mediated catabolite repression control on the production of glycine betaine catabolic enzymes in Pseudomonas aeruginosa PAO1 under low and elevated salinities.
2006 May
High-yield cultivation of Marinococcus M52 for production and recovery of hydroxyectoine.
2006 Sep
In vivo assessment of Ectoin: a randomized, vehicle-controlled clinical trial.
2007
The role of LRP and H-NS in transcription regulation: involvement of synergism, allostery and macromolecular crowding.
2007 Feb 23
Halomonas alkaliantarctica sp. nov., isolated from saline lake Cape Russell in Antarctica, an alkalophilic moderately halophilic, exopolysaccharide-producing bacterium.
2007 Jan
In vivo skin antioxidant effect of a new combination based on a specific Vitis vinifera shoot extract and a biotechnological extract.
2007 Jun
[Detection of osmoprotector ectoine content in methylotrophic bacteria using of normal-phase high performance liquid chromatography].
2007 Mar-Apr
Ectoine as a natural component of food: detection in red smear cheeses.
2007 Nov
Compatible solutes from hyperthermophiles improve the quality of DNA microarrays.
2007 Nov 23
Response of Halomonas campisalis to saline stress: changes in growth kinetics, compatible solute production and membrane phospholipid fatty acid composition.
2007 Sep
Characterization of compatible solute transporter multiplicity in Corynebacterium glutamicum.
2007 Sep
Microbial life at high salt concentrations: phylogenetic and metabolic diversity.
2008 Apr 15
Proteomics with a pinch of salt: a cyanobacterial perspective.
2008 Apr 15
Regulation of osmoadaptation in the moderate halophile Halobacillus halophilus: chloride, glutamate and switching osmolyte strategies.
2008 Apr 28
Cloning and heterologous expression of ectoine biosynthesis genes from Bacillus halodurans in Escherichia coli.
2008 Aug
Cloning and characterization of the gene cluster for biosynthesis of ectoine from Nesterenkonia halobia DSM 20541.
2008 Jun
Characterization of the recombinant diaminobutyric acid acetyltransferase from Methylophaga thalassica and Methylophaga alcalica.
2008 Jun
Compatible solute influence on nucleic acids: many questions but few answers.
2008 Jun 3
[Cloning and characterization of ectABC cluster from Bacillus alcalophilus DTY1].
2008 Mar
Responses of a novel salt-tolerant Streptomyces albidoflavus DUT_AHX capable of degrading nitrobenzene to salinity stress.
2009 Feb
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 18:57:38 GMT 2023
Edited
by admin
on Fri Dec 15 18:57:38 GMT 2023
Record UNII
7GXZ3858RY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ECTOINE
MI   WHO-DD  
Common 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
ECTOIN [INCI]
Common Name English
ECTOINE [MI]
Common Name English
ECTOIN
INCI  
INCI  
Official Name English
Code System Code Type Description
CAS
96702-03-3
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
EVMPD
SUB179034
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
WIKIPEDIA
ECTOINE
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
PUBCHEM
126041
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
CHEBI
27592
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID50869280
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
RXCUI
1426644
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY RxNorm
MESH
C045628
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
MERCK INDEX
m4822
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY Merck Index
FDA UNII
7GXZ3858RY
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
SMS_ID
100000164557
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
NCI_THESAURUS
C185154
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
DAILYMED
7GXZ3858RY
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY
NSC
614616
Created by admin on Fri Dec 15 18:57:38 GMT 2023 , Edited by admin on Fri Dec 15 18:57:38 GMT 2023
PRIMARY