Ectoine

• CAS: 96702-03-3
• Catalog Number: ACM96702033
• Category: Other Products
• Molecular Weight: 142.16
• Molecular Formula: C6H10N2O2
• Description: 4-pyrimidincarbonsure (1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a compatible solute which serves as a protective substance by acting as an osmolyte and thus helps organisms survive extreme osmotic stress. 4-pyrimidincarbonsure is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. 4-pyrimidincarbonsure was first identified in the microorganism Ectothiorhodospira halochloris, but has since been found in a wide range of Gram-negative and Gram-positive bacteria. Other species of 4-pyrimidincarbonsure were found in
• Synonyms: (S)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidincarbonsure
• IUPAC Name: (6S)-2-methyl-1,4,5,6-tetrahydropyrimidine-6-carboxylic acid
• Canonical SMILES: CC1=NCC[C@H](N1)C(=O)O
• InChI: 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
• Melting Point: 280 °C
• Flash Point: 184.5ºC
• Density: 1.37 g/ml
• Appearance: White powder
• Complexity: 177
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Exact Mass: 142.074227566
• Hazard Codes: Xi
• Hazard Statements: Xi
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Isomeric SMILES: CC1=NCC[C@H](N1)C(=O)O
• LogP: -0.38430
• Monoisotopic Mass: 142.074227566
• pH: 6-8
• Physical State: Powder
• pKa: 3.14±0.20
• PSA: 61.69
• Refractive Index: 1.596
• Rotatable Bond Count: 1
• Safety Description: 26-36
• Topological Polar Surface Area: 61.7 Ų

Case Study

Therapeutic Potential of Ectoine as A Promising Protective Agent in Human and Animals

Bownik A, et al. Arhiv za higijenu rada i toksikologiju, 2016, 67(4), 260-264.

Many biophysical studies have shown that ectoine binds to water molecules even better than some other osmoprotectants such as glycerol. Ectoine exhibits therapeutic potential in multiple aspects in humans and animals.
· Skin Protection: Ectoine has been widely used in cosmetic anti-aging and moisturizers to improve the skin's tolerance to surfactants in skin cleansing solutions. Ectoine is also an effective long-lasting moisturizer and can strongly absorbs ultraviolet (UV) radiation.
· Stabilizes enzyme activity: Ectoine increases the stability of enzymes that maintain hydration, thereby reducing the susceptibility to protein denaturation.
· Cell protection: Ectoine may protect cells from various environmental stressors in a variety of ways, such as increasing cell membrane fluidity and improving cell surface hydration.
· Reduce inflammatory response: Tetrahydromethylpyrimidine can effectively reduce inflammation. For example, nasal sprays and air drops containing ectoine are effective treatments for allergic rhinitis, rhinoconjunctivitis, and dry eye syndrome.
· Cryoprotection: Compatible solutes such as ectoine and hydroxyectoine are effective reagents for cryopreservation.
· Preventing Neurodegenerative Diseases: Ectoine has been found to prevent amyloid formation and delay the onset and progression of Alzheimer's disease.

Biosynthetic Pathway and Transformation of Ectoine

Kunte H J, et al. Current Biotechnology, 2014, 3(1), 10-25.

Ectoine is produced industrially through biotechnological processes using the halophilic γ-proteobacterium H. elongata. Ectoine is synthesized from aspartate semialdehyde, and its formation involves three enzymatic steps. In addition, ectoine can be further converted into 5-hydroxyectoine under the action of ectoine hydroxylase.
· Initially, aspartate-semialdehyde is transaminated to 2,4-diaminobutyric acid (DABA) using glutamate as the amino-group donor, catalyzed by DABA transaminase EctB. Gel filtration tests with purified protein from H. elongata suggest that DABA aminotransferase EctB may form a homohexamer in its natural state.
· Subsequently, DABA-Nγ-acetyltransferase EctA transfers an acetyl group from acetyl-CoA to DABA to produce Nγ-acetyl-L-2,4-diaminobutyric acid.
· Lastly, EctC, an ectoine synthase, facilitates the cyclic condensation of Nγ-acetyl-2,4-diaminobutyric acid to produce ectoine. Belonging to the enzyme family of carbon-oxygen lyases, in vitro tests with purified EctC demonstrate that its ectoine-synthase activity and substrate affinity are significantly impacted by NaCl.
· Under certain stress conditions (e.g. elevated temperatures) H. elongata converts some of the ectoine to 5- hydroxyectoine by ectoine hydroxylase (EctD) catalysis.

Custom Q&A

What is the molecular formula of Ectoine according to the reference?

The molecular formula of Ectoine is C6H10N2O2.

What is the molecular weight of Ectoine?

The molecular weight of Ectoine is 142.16 g/mol.

What is the InChIKey for Ectoine?

The InChIKey for Ectoine is WQXNXVUDBPYKBA-YFKPBYRVSA-N.

How many hydrogen bond donors does Ectoine have?

Ectoine has 2 hydrogen bond donors.

What is the exact mass of Ectoine?

The exact mass of Ectoine is 142.074227566 g/mol.

How many hydrogen bond acceptors does Ectoine have?

Ectoine has 3 hydrogen bond acceptors.

What is the CAS number for Ectoine?

The CAS number for Ectoine is 96702-03-3.

What is the complexity of Ectoine?

The complexity of Ectoine is computed by PubChem.

In what year was Ectoine created in the database?

Ectoine was created in the database on 2005-07-19.

What role does Ectoine play according to the reference?

Ectoine has a role as an osmolyte.