Cas no 597-44-4 (2-hydroxy-2-methylbutanedioic acid)

2-Hydroxy-2-methylbutanedioic acid is a dicarboxylic acid derivative with a hydroxyl group at the α-position, offering versatile reactivity in organic synthesis and industrial applications. Its unique structure enables chelation and coordination properties, making it useful in metal ion sequestration and catalysis. The compound’s bifunctional nature (carboxylic and hydroxyl groups) allows for esterification, polymerization, and derivatization, supporting its role in specialty chemicals and pharmaceutical intermediates. It exhibits moderate water solubility and stability under standard conditions, facilitating handling in aqueous and non-aqueous systems. The presence of both acidic and hydroxyl functionalities enhances its utility in asymmetric synthesis and chiral resolution processes, providing a valuable building block for fine chemical production.
2-hydroxy-2-methylbutanedioic acid structure
597-44-4 structure
Product Name:2-hydroxy-2-methylbutanedioic acid
CAS No:597-44-4
MF:C5H8O5
MW:148.114022254944
CID:1622423
PubChem ID:1081
Update Time:2025-11-02

2-hydroxy-2-methylbutanedioic acid Chemical and Physical Properties

Names and Identifiers

    • ()-2-hydroxy-2-methylsuccinic acid
    • (1)-2-Hydroxy-2-methylsuccinic acid
    • 2-hydroxy-2-methylbutanedioic acid
    • AT23394
    • EINECS 209-901-5
    • (b)-2-Methylmalic acid
    • alpha-Hydroxypyrotartaric acid
    • 2-Hydroxy-2-methylbutane-1,4-dioic acid
    • (RS)-citramalic acid
    • 597-44-4
    • (+/-)-Citramalic acid dipotassium salt
    • entecavirhydrate
    • 2306-22-1
    • Citramalic acid
    • (+/-)-.ALPHA.-METHYLMALIC ACID
    • (r,s)-b-methylmalic acid
    • (+/-)-2-METHYLMALIC ACID
    • AKOS024319127
    • NSC 80648
    • NS00014571
    • (b)-2-Methylmalate
    • 20C88B9D-45B9-4A5D-B2F1-B824903784F3
    • EN300-109891
    • UNII-FGC721P65H
    • 2-Hydroxy-2-methyl-butanedioic acid
    • NSC80648
    • FT-0605274
    • (S)-(+)-CITRAMALICACID
    • (+/-)-Citramalic acid sodium salt
    • (R,S)-beta-Methylmalate
    • Malic acid, 2-methyl-
    • (R,S)-(b)-Citramalate
    • DL-Citramalate
    • 2-hydroxy-2-methyl-(b)-Butanedioate
    • C00815
    • XFTRTWQBIOMVPK-UHFFFAOYSA-N
    • Z1255442426
    • butanedioic acid, 2-hydroxy-2-methyl-
    • (R,S)-b-Methylmalate
    • 2-Deoxy-3-C-methyltetrarate
    • FT-0773291
    • 2-Hydroxy-2-methylsuccinicacid
    • (b)-Citramalate
    • (R,S)-beta-Methylmalic acid
    • DL-Citramalic acid
    • 2-methyl-(b)-Malate
    • SCHEMBL61203
    • 2-hydroxy-2-methyl-(b)-Butanedioic acid
    • FT-0726023
    • citramalate
    • (+-)-2-hydroxy-2-methylsuccinic acid
    • 2-Methylmalic acid
    • 2-hydroxy-2-methylbutanedioate
    • alpha-methylmalate
    • CITRAMALIC ACID [MI]
    • CHEBI:15584
    • Q27098121
    • 2-methyl-(b)-Malic acid
    • CS-0231763
    • CITRAMALIC ACID, (+/-)-
    • 2-Hydroxy-2-methyl-butanedioate
    • (+/-)-CITRAMALIC ACID
    • 2-Deoxy-3-C-methyltetraric acid
    • (b)-Citramalic acid
    • (R,S)-(b)-Citramalic acid
    • FGC721P65H
    • 2-Hydroxy-2-methylsuccinic acid
    • 102601-31-0
    • DTXSID40862265
    • NSC-80648
    • DS-013391
    • 1ST167179
    • DB-057850
    • Inchi: 1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)
    • InChI Key: XFTRTWQBIOMVPK-UHFFFAOYSA-N
    • SMILES: OC(C(=O)O)(C)CC(=O)O

Computed Properties

  • Exact Mass: 148.037
  • Monoisotopic Mass: 148.037
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 3
  • Complexity: 163
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: _0.9
  • Topological Polar Surface Area: 94.8A^2

Experimental Properties

  • Density: 1.513
  • Boiling Point: 295.2°C at 760 mmHg
  • Flash Point: 146.6°C
  • Refractive Index: 1.521
  • PSA: 100.49000
  • LogP: -3.37270

2-hydroxy-2-methylbutanedioic acid Pricemore >>

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Additional information on 2-hydroxy-2-methylbutanedioic acid

2-Hydroxy-2-Methylbutanedioic Acid (CAS 597-44-4): Properties, Applications, and Market Insights

2-Hydroxy-2-methylbutanedioic acid (CAS 597-44-4), also known as hydroxymethylsuccinic acid, is a versatile organic compound with significant applications in various industries. This hydroxy derivative of butanedioic acid has garnered attention due to its unique chemical properties and broad utility in food additives, pharmaceutical intermediates, and biodegradable materials. As sustainability and green chemistry become hot topics in 2024, researchers are increasingly exploring this compound's potential in eco-friendly applications.

The molecular structure of 2-hydroxy-2-methylbutanedioic acid features both carboxyl and hydroxyl functional groups, making it particularly interesting for chelation chemistry and metal ion binding. Its water solubility and moderate acidity (pKa values around 3.5 and 5.5) contribute to its usefulness in buffer systems. Recent studies highlight its potential in nutraceutical formulations, where it may enhance mineral bioavailability - a trending topic in nutritional science as consumers seek better absorption of essential nutrients.

In the food industry, 2-hydroxy-2-methylbutanedioic acid serves as an acidulant and flavor enhancer, particularly in low-pH beverages. Its gradual acid release profile makes it preferable to citric acid in certain applications, addressing current consumer demands for clean-label ingredients and reduced sourness impact. Food scientists are investigating its synergy with natural sweeteners to reduce sugar content - a key focus area as global sugar reduction initiatives gain momentum.

The pharmaceutical applications of CAS 597-44-4 are expanding, particularly in drug delivery systems. Its ability to form stable complexes with various active pharmaceutical ingredients (APIs) makes it valuable for improving drug solubility - a major challenge in modern pharma development. Recent patent filings reveal its use in extended-release formulations, aligning with the growing market for controlled-release medications that improve patient compliance.

From an industrial perspective, hydroxymethylsuccinic acid shows promise in biodegradable polymer production. As plastic pollution remains a top environmental concern, researchers are evaluating this compound as a potential monomer for sustainable plastics. Its branched structure could impart desirable mechanical properties while maintaining biodegradability - addressing two critical needs in the packaging industry's shift toward circular economy models.

The synthesis of 2-hydroxy-2-methylbutanedioic acid typically involves chemical oxidation or fermentation processes. Recent advancements in biocatalytic production methods have improved yield and sustainability, responding to industry demands for greener manufacturing. Analytical techniques like HPLC and NMR spectroscopy are essential for quality control, ensuring the compound meets stringent purity requirements for various applications.

Market analysis indicates steady growth for CAS 597-44-4, driven by increasing demand in Asia-Pacific food and pharmaceutical sectors. Price trends show moderate fluctuations tied to raw material availability, with current market prices ranging between $XX-XX/kg depending on purity grade. Regulatory status varies by region, but generally falls under GRAS (Generally Recognized As Safe) for food applications in major markets, making it attractive for global product formulations.

Future research directions for 2-hydroxy-2-methylbutanedioic acid include exploring its cosmeceutical potential in skincare formulations and investigating its role in plant growth enhancement. These applications align with booming markets for anti-aging products and sustainable agriculture solutions. Additionally, its potential as a corrosion inhibitor in mild steel applications is being studied, which could open new industrial markets.

For researchers and manufacturers working with hydroxymethylsuccinic acid, proper storage conditions (typically room temperature in sealed containers) and handling procedures are essential to maintain stability. While not classified as hazardous, standard laboratory precautions should be followed. The compound's hygroscopic nature requires attention to moisture control during storage and processing to ensure consistent performance in end applications.

In conclusion, 2-hydroxy-2-methylbutanedioic acid (CAS 597-44-4) represents an increasingly important specialty chemical with diverse applications across multiple industries. Its combination of functional properties, regulatory acceptance, and emerging applications in sustainable technologies positions it well for continued market growth. As industries prioritize green chemistry and multifunctional additives, this compound's versatility ensures its relevance in addressing current and future technological challenges.

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