Ectoin
[CAS# 96702-03-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Methyl pyrimidine
• Name: Ectoin
• Synonyms: (S)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid; Ectoine; NSC 614616; Pyrostatin B; Pyrostatine B; RonaCare
• Molecular Formula: C₆H₁₀N₂O₂
• Molecular Weight: 142.16
• CAS Registry Number: 96702-03-3
• EC Number: 431-910-1
• SMILES: CC1=NCC[C@H](N1)C(=O)O

Properties

• Solubility: 2.048e+004 mg/L (25 °C water)
• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.597, Calc.^*
• Melting point: 135.49 °C
• Boiling Point: 381.5±35.0 °C (760 mmHg), Calc.^*, 365.88 °C
• Flash Point: 184.5±25.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Ectoins are natural compounds with remarkable properties that were discovered in halophilic microorganisms that survive in harsh environments such as deserts, salt flats and hot springs. Ectoins were first isolated and identified from the halophilic bacterium Ectothiorhodospira halochloris by a research team led by Dr. Maja Hofmann in the late 20th century.

Ectoins have the unique ability to protect cells from environmental stressors such as high salinity, extreme temperatures and UV radiation.Ectoins are widely used in the cosmetics industry for their skin-soothing, moisturizing and anti-aging properties, protecting against environmental stressors including pollution, UV radiation and oxidative damage, helping to keep the skin healthy and vibrant.Ectoins have therapeutic applications in dermatology, where they are used to treat a variety of skin conditions, including atopic dermatitis, psoriasis and eczema. Its anti-inflammatory and immunomodulatory effects help relieve symptoms associated with these inflammatory skin conditions, such as itching, redness and dryness. Topical medications and emollients containing ectoins relieve discomfort and promote skin healing, improving the quality of life for patients with chronic skin conditions. Ectoin is incorporated into ophthalmic solutions and eye drops for the treatment of dry eyes and other ocular surface diseases. Eye care products containing ectoin provide long-lasting moisturization and lubrication, improve eye comfort and support overall eye health. Ectoin is used in oral care products such as toothpaste and mouthwash for its anti-inflammatory and antimicrobial properties. It helps reduce gum inflammation, prevents bacterial growth, and protects against oral infections such as gingivitis and periodontitis. Ectoin has wound healing properties and can be incorporated into wound care products such as gels and dressings to promote tissue regeneration and accelerate the healing process. It forms a protective barrier at the wound site, preventing microbial contamination and reducing the risk of infection. Ectoin is used in the manufacture of medical devices such as contact lenses, wound dressings, and catheters to impart biocompatibility and reduce the risk of inflammation and infection. Ectoin is biocompatible and has low cytotoxicity, making it suitable for incorporation into a variety of medical materials and implants to ensure compatibility with biological tissues and minimize adverse reactions. Ectoin is incorporated into various personal care products such as deodorants, shaving creams and hair care formulas for its skin conditioning and protective properties.

References

2024. The tropical marine actinomycete Nocardiopsis dassonvillei NCIM 5124 as novel source of ectoine: Genomic and transcriptomic insights. Gene, 933.
DOI: 10.1016/j.gene.2024.148860

2024. Ectoine enhances recombinant antibody production in Chinese hamster ovary cells by promoting cell cycle arrest. New Biotechnology, 83.
DOI: 10.1016/j.nbt.2024.06.006

2024. Ectoine maintains the flavor and nutritional quality of broccoli during postharvest storage. Food Chemistry, 459.
DOI: 10.1016/j.foodchem.2024.140204