(6S)-2-methyl-3,4,5,6-tetrahydropyrimidin-1-ium-6-carboxylate

Base Information

• Chemical Name: (6S)-2-methyl-3,4,5,6-tetrahydropyrimidin-1-ium-6-carboxylate
• CAS No.: 96702-03-3
• Molecular Formula: C6H10 N2 O2
• Molecular Weight: 142.158
• Mol file: 96702-03-3.mol

Synonyms:ectoine zwitterion;1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid;CHEBI:58515;(6S)-2-methyl-3,4,5,6-tetrahydropyrimidin-1-ium-6-carboxylate

Chemical Property of (6S)-2-methyl-3,4,5,6-tetrahydropyrimidin-1-ium-6-carboxylate

Chemical Property:

• Vapor Pressure: 7.09E-07mmHg at 25°C
• Melting Point: ~280°
• Boiling Point: 381.5°Cat760mmHg
• PKA: 3.14±0.20(Predicted)
• Flash Point: 184.5°C
• PSA: 61.69000
• Density: 1.37g/cm³
• LogP: -0.38430
• Storage Temp.: 2-8°C
• Solubility.: methanol: 20 mg/mL, clear, colorless
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.074227566
• Heavy Atom Count: 10
• Complexity: 171

Purity/Quality:

99% up ^*data from raw suppliers

(S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=[NH+]CCC(N1)C(=O)[O-]
• Isomeric SMILES: CC1=[NH+]CC[C@H](N1)C(=O)[O-]
• Description: Ectoine is a carboxamidine heterocycle obtained by formal condensation of (2S)-2,4-diaminobutanoic acid with acetic acid. It has a role as an osmolyte. It is a carboxamidine, a member of 1,4,5,6-tetrahydropyrimidines and a monocarboxylic acid. It is a conjugate acid of an ectoinate. It is a tautomer of an ectoine zwitterion. Ectoine is a cyclic tetrahydropyrimidine organic osmolyte, which was discovered in the halophilic bacterium Ectothiorhodospira halochloris. It is the most abundant solute produced by aerobic heterotrophic eubacteria and has been extensively characterized as an osmoprotectant and stabilizer for cells and biomolecules.Ectoine is considered a member of the small molecule chaperones family (SMCs). SMCs accumulate to high intracellular concentrations, preventing the misfolding/ denaturation of proteins and other labile macromolecules.? Ectoine preserves enzymes and whole cells against harmful conditions such as freezing, drying, or heating. This molecule, among other compatible solutes, possesses the ability to conserve the proteolytic activity of trypsin and chymotrypsin. It has been shown to induce heat shock proteins and downregulate proinflammatory signals in human keratinocytes. It is not toxic to the cellular environment, even at concentrations as high as 100 mM.Ectoine strongly inhibits the Ab42 amyloid formation in vitro, reducing the toxicity to human neurblastoma cells. Ab42 was found to be the most predominant proteolytic fragment found in amyloid plaques, thus, ectoine may act as a potential inhibitor associated with neurodegenerative diseases.
• Uses: Ectoine is a natural protector that stabilizes proteins and other cell structures and protects the skin from stresses such as UV exposure and dryness.

Technology Process of (6S)-2-methyl-3,4,5,6-tetrahydropyrimidin-1-ium-6-carboxylate

There total 1 articles about (6S)-2-methyl-3,4,5,6-tetrahydropyrimidin-1-ium-6-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-γ-acetyl-L-2,4-diaminobutyrate (1190-46-1) → ectoin (96702-03-3)

Guidance literature:

With l-ectoine synthase; Enzymatic reaction;

DOI:10.1002/anie.202105667

Reference yield:

ectoin (96702-03-3) + N-benzyl-trimethylammonium hydroxide (100-85-6) → benzyltrimethylammonium 2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylate

Guidance literature:

In water; at 20 - 90 ℃;

upstream raw materials:

N-γ-acetyl-L-2,4-diaminobutyrate

Refernces