Cas no 128899-79-6 ((S)-4,4,4-Trifluoro-3-hydroxybutyric acid)

(S)-4,4,4-Trifluoro-3-hydroxybutyric acid is a chiral fluorinated organic compound with significant utility in pharmaceutical and agrochemical synthesis. Its trifluoromethyl group enhances metabolic stability and bioavailability, making it a valuable intermediate for bioactive molecules. The (S)-enantiomer offers stereochemical precision, crucial for asymmetric synthesis and enzyme-targeted applications. The hydroxyl and carboxylic acid functionalities provide versatile reactivity for further derivatization, including esterification, amidation, or reduction. This compound is particularly useful in the development of fluorinated analogs of natural products and fine chemicals. High purity grades ensure consistent performance in research and industrial processes. Its stability under standard storage conditions further supports handling and long-term use.
(S)-4,4,4-Trifluoro-3-hydroxybutyric acid structure
128899-79-6 structure
Product Name:(S)-4,4,4-Trifluoro-3-hydroxybutyric acid
CAS No:128899-79-6
MF:C4H5F3O3
MW:158.075912237167
MDL:MFCD03093018
CID:105607
PubChem ID:7000146
Update Time:2025-05-20

(S)-4,4,4-Trifluoro-3-hydroxybutyric acid Chemical and Physical Properties

Names and Identifiers

    • (S)-4,4,4-Trifluoro-3-hydroxybutyric acid
    • (3S)-3-HYDROXY-4,4,4-TRIFLUOROBUTANOIC ACID
    • (3S)-3-Hydroxy-4,4,4-trifluorobutyric acid
    • Butanoicacid, 4,4,4-trifluoro-3-hydroxy-, (3S)-
    • (3S)-4,4,4-trifluoro-3-hydroxybutanoic acid
    • (S)-(-)-(2-hydroxy-3,3,3-trifluoropropyl)phenyl ketone
    • (S)-(-)-3,3,3-trifluoro-2-hydroxypropyl phenyl ketone
    • (S)-4,4,4-trifluoro-3-hydroxy-1-phenyl-1-butanone
    • (S)-4,4,4-trifluoro-3-hydroxy-1-phenylbutan-1-one
    • (S)-4,4,4-trifluoro-3-hydroxybutanoic acid
    • 1-Butanone, 4,4,4-trifluoro-3-hydroxy-1-phenyl-, (3S)-
    • CTK0C5524
    • SureCN6897943
    • S-TFHBA
    • (S)-3-HYDROXY-4,4,4-TRIFLUOROBUTYRIC ACID
    • MFCD03093017
    • 128899-79-6
    • EN300-1932684
    • SCHEMBL1967208
    • (R)-3-Hydroxy-4,4,4-trifluorobutyric acid
    • Butanoicacid,4,4,4-trifluoro-3-hydroxy-,(3S)-
    • CS-0344978
    • AKOS005063872
    • butanoic acid, 4,4,4-trifluoro-3-hydroxy-, (3s)-
    • ASQMUMZEQLWJRC-REOHCLBHSA-N
    • (S)-4,4,4-Trifluoro-3-hydroxybutyricacid
    • MDL: MFCD03093018
    • Inchi: 1S/C4H5F3O3/c5-4(6,7)2(8)1-3(9)10/h2,8H,1H2,(H,9,10)/t2-/m0/s1
    • InChI Key: ASQMUMZEQLWJRC-REOHCLBHSA-N
    • SMILES: FC([C@H](CC(=O)O)O)(F)F

Computed Properties

  • Exact Mass: 285.92732
  • Monoisotopic Mass: 158.019
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 130
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 57.5A^2
  • XLogP3: 0.2

Experimental Properties

  • Color/Form: NA
  • Density: 1.5±0.1 g/cm3
  • Melting Point: Not available
  • Boiling Point: 261.3±40.0 °C at 760 mmHg
  • Flash Point: 122.2±14.2 °C
  • Refractive Index: 1.42
  • PSA: 0
  • LogP: 0.38430

(S)-4,4,4-Trifluoro-3-hydroxybutyric acid Pricemore >>

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Additional information on (S)-4,4,4-Trifluoro-3-hydroxybutyric acid

Introduction to (S)-4,4,4-Trifluoro-3-hydroxybutyric acid (CAS No. 128899-79-6)

(S)-4,4,4-Trifluoro-3-hydroxybutyric acid (CAS No. 128899-79-6) is a chiral compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This compound belongs to the class of trifluorinated carboxylic acids and is characterized by the presence of a trifluoromethyl group and a hydroxyl group on the butyric acid backbone. The chiral center at the third carbon position imparts enantiomeric specificity, which is crucial for its biological activities.

The synthesis of (S)-4,4,4-Trifluoro-3-hydroxybutyric acid has been extensively studied, with various methods reported in the literature. One common approach involves the asymmetric synthesis of the chiral center using catalytic asymmetric hydrogenation or enzymatic resolution techniques. These methods ensure high enantiomeric purity, which is essential for pharmaceutical applications where enantiomeric purity can significantly impact the efficacy and safety of a drug.

Recent research has highlighted the potential of (S)-4,4,4-Trifluoro-3-hydroxybutyric acid in various therapeutic areas. One notable application is in the treatment of metabolic disorders, particularly those involving dysregulated lipid metabolism. Studies have shown that this compound can modulate key enzymes involved in fatty acid metabolism, such as acetyl-CoA carboxylase (ACC) and fatty acid synthase (FAS), thereby potentially reducing lipid accumulation in tissues.

In addition to its metabolic effects, (S)-4,4,4-Trifluoro-3-hydroxybutyric acid has been investigated for its anti-inflammatory properties. In vitro and in vivo studies have demonstrated that this compound can inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6, suggesting its potential as an anti-inflammatory agent. This property makes it a promising candidate for the treatment of inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

The pharmacokinetic properties of (S)-4,4,4-Trifluoro-3-hydroxybutyric acid have also been studied to understand its behavior in biological systems. Research has shown that this compound exhibits good oral bioavailability and a favorable pharmacokinetic profile, making it suitable for oral administration. Furthermore, its stability in physiological conditions ensures that it remains active during transit through the gastrointestinal tract.

Clinical trials are currently underway to evaluate the safety and efficacy of (S)-4,4,4-Trifluoro-3-hydroxybutyric acid in human subjects. Preliminary results from phase I trials have indicated that the compound is well-tolerated at therapeutic doses with no significant adverse effects reported. These findings are encouraging and pave the way for further clinical development.

The potential applications of (S)-4,4,4-Trifluoro-3-hydroxybutyric acid extend beyond traditional pharmaceuticals. It has also been explored as a building block for the synthesis of more complex molecules with diverse biological activities. For example, it can be used as a precursor for the synthesis of prodrugs designed to enhance drug delivery and reduce side effects.

In conclusion, (S)-4,4,4-Trifluoro-3-hydroxybutyric acid (CAS No. 128899-79-6) is a versatile chiral compound with significant potential in various therapeutic areas. Its unique structural features and biological activities make it an attractive candidate for further research and development. As ongoing studies continue to uncover new insights into its mechanisms of action and therapeutic applications, it is likely that this compound will play an increasingly important role in the future of medicinal chemistry and pharmaceutical science.

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