Cas no 13244-78-5 ((R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid)

(R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid is a chiral hydroxy acid derivative with significant applications in pharmaceutical and fine chemical synthesis. Its key structural features include a hydroxyl group at the 4-position of the phenyl ring and a stereocenter at the α-carbon, making it a valuable intermediate for enantioselective synthesis. This compound is particularly useful in the production of optically active pharmaceuticals and agrochemicals due to its ability to impart stereochemical control. Its phenolic and carboxylic acid functionalities also allow for further derivatization, enhancing its versatility in organic synthesis. High purity and well-defined stereochemistry ensure consistent performance in research and industrial applications.
(R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid structure
13244-78-5 structure
Product Name:(R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid
CAS No:13244-78-5
MF:C8H8O4
MW:168.146722793579
CID:1025992
PubChem ID:440639
Update Time:2025-06-09

(R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid Chemical and Physical Properties

Names and Identifiers

    • (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid
    • (R)-4-Hydroxymandelate
    • (R)-4-Hydroxymandelic acid
    • 4-hydroxy-D-mandelic acid
    • 4-Hydroxy-D-mandelsaeure
    • AC1L99O6
    • ANW-68645
    • CHEBI:32803
    • CTK8C2588
    • SureCN467741
    • PHMA
    • Pisolithin B
    • (R)-4,α-Dihydroxybenzeneacetic acid
    • (R)-Hydroxy(4-hydroxyphenyl)acetic acid
    • 8NMA4Q2GDG
    • UNII-8NMA4Q2GDG
    • BENZENEACETIC ACID, .ALPHA.,4-DIHYDROXY-, (.ALPHA.R)-
    • SCHEMBL467741
    • (2R)-hydroxy(4-hydroxyphenyl)acetic acid
    • 4-Hydroxymandelic acid, (R)-
    • R)-(-)-p-hydroxymandelic acid
    • (R)-2-Hydroxy-2-(4-hydroxyphenyl)aceticacid
    • Q27104224
    • 13244-78-5
    • (r)-(-)-p-hydroxymandelic acid
    • (2R)-2-hydroxy-2-(4-hydroxyphenyl)acetic acid
    • C05343
    • (-)-4-Hydroxymandelic acid
    • 4-Hydroxymandelic acid, D-
    • Benzeneacetic acid, alpha,4-dihydroxy-, (alphaR)-
    • DB-327973
    • F76817
    • MDL: MFCD00798432
    • Inchi: 1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)/t7-/m1/s1
    • InChI Key: YHXHKYRQLYQUIH-SSDOTTSWSA-N
    • SMILES: O[C@@H](C(=O)O)C1C=CC(=CC=1)O

Computed Properties

  • Exact Mass: 168.04225873g/mol
  • Monoisotopic Mass: 168.04225873g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 160
  • 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
  • XLogP3: 0.3
  • Topological Polar Surface Area: 77.8?2

(R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid Pricemore >>

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Additional information on (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid

Recent Advances in the Study of (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid (CAS: 13244-78-5)

The compound (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid (CAS: 13244-78-5) has garnered significant attention in the field of chemical biology and pharmaceutical research due to its potential therapeutic applications. This chiral molecule, characterized by its hydroxyl and carboxyl functional groups, has been the subject of recent studies focusing on its synthesis, biological activity, and pharmacological properties. The latest research highlights its role as a key intermediate in the production of bioactive compounds and its potential as a therapeutic agent in various diseases.

Recent studies have explored the efficient synthesis of (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid using biocatalytic methods, which offer advantages such as high enantioselectivity and environmental sustainability. Researchers have employed enzymes like hydroxynitrile lyases and engineered ketoreductases to achieve high yields and purity of the (R)-enantiomer. These advancements are critical for scaling up production and ensuring the compound's availability for further pharmacological studies.

In terms of biological activity, (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid has demonstrated promising anti-inflammatory and antioxidant properties. In vitro studies have shown that the compound can inhibit the production of pro-inflammatory cytokines and reactive oxygen species, suggesting its potential in treating inflammatory diseases such as rheumatoid arthritis and neurodegenerative disorders. Additionally, its chiral nature has been found to play a crucial role in its interaction with biological targets, underscoring the importance of enantiopure synthesis.

Pharmacological evaluations have further revealed that (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid exhibits favorable pharmacokinetic properties, including good oral bioavailability and metabolic stability. Animal studies have indicated its ability to cross the blood-brain barrier, making it a candidate for central nervous system-targeted therapies. These findings are supported by molecular docking studies, which highlight the compound's affinity for key enzymes and receptors involved in disease pathways.

The potential applications of (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid extend beyond its direct therapeutic use. Recent research has explored its incorporation into prodrugs and drug delivery systems, leveraging its functional groups for conjugation with other bioactive molecules. Such strategies aim to enhance drug solubility, stability, and targeted delivery, thereby improving therapeutic outcomes.

In conclusion, the latest research on (R)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid (CAS: 13244-78-5) underscores its versatility and potential in chemical biology and pharmaceutical development. Advances in synthesis, coupled with a deeper understanding of its biological and pharmacological properties, pave the way for its future application in drug discovery and therapy. Continued research is expected to further elucidate its mechanisms of action and expand its therapeutic scope.

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