Cas no 595-30-2 (DL-Camphoric anhydride)

DL-Camphoric anhydride (C10H14O3) is a bicyclic organic compound derived from camphoric acid. It serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, fragrances, and specialty chemicals. The anhydride form enhances reactivity, making it suitable for esterification and polymerization reactions. Its rigid bicyclic structure contributes to stereochemical control in asymmetric synthesis. The compound exhibits high purity and stability under standard conditions, ensuring consistent performance in laboratory and industrial applications. DL-Camphoric anhydride is also valued for its role in producing optically active compounds, leveraging its chiral centers for enantioselective transformations. Proper handling requires adherence to standard safety protocols for anhydrides.
DL-Camphoric anhydride structure
DL-Camphoric anhydride structure
Product Name:DL-Camphoric anhydride
CAS No:595-30-2
MF:C10H14O3
MW:182.216363430023
CID:82639
PubChem ID:94834
Update Time:2025-10-31

DL-Camphoric anhydride Chemical and Physical Properties

Names and Identifiers

    • DL-Camphoric anhydride
    • DL-Camphor Anhydride
    • (±)-Camphoric anhydride
    • 5,8,8-trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
    • (-) camphoric anhydride
    • NSC-4559
    • 3-Oxabicyclo[3.2.1]octane-2,4-dione, 1,8,8-trimethyl-, (1S)-
    • 76-32-4
    • d-Camphoric anhydride
    • FT-0624349
    • NS00080568
    • 3-Oxabicyclo[3.2.1]octane-2, 1,8,8-trimethyl-
    • NSC60293
    • Camphoric anhydride
    • DTXSID90871781
    • NSC657821
    • F0848-0104
    • NSC-60293
    • SCHEMBL426068
    • 3-Oxabicyclo[3.2.1]octane-2,4-dione, 1,8,8-trimethyl-
    • CHEMBL1978242
    • NSC-657821
    • AMY31071
    • AKOS002162374
    • AKOS016290126
    • 595-30-2
    • FT-0623432
    • NSC4559
    • 1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
    • FT-0623433
    • (+/-)-camphoric anhydride
    • 1, 1,2,2-trimethyl-
    • 1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione #
    • NCI60_020164
    • (1R)-Camphoric anhydride
    • 3-Oxabicyclo[3.2.1]octane-2, 1,8,8-trimethyl-, (.+-.)-
    • G77799
    • (+/-)-Camphoric acid anhydride
    • MDL: MFCD00067307
    • Inchi: 1S/C10H14O3/c1-9(2)6-4-5-10(9,3)8(12)13-7(6)11/h6H,4-5H2,1-3H3
    • InChI Key: VFZDNKRDYPTSTP-UHFFFAOYSA-N
    • SMILES: O1C(C2CCC(C1=O)(C)C2(C)C)=O

Computed Properties

  • Exact Mass: 182.09400
  • Monoisotopic Mass: 182.094
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 293
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 2
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: 1.8
  • Topological Polar Surface Area: 43.4

Experimental Properties

  • Color/Form: Not available
  • Density: 1.1940
  • Melting Point: 222-225?°C
  • Boiling Point: 270 °C
  • Flash Point: 121.1 °C
  • Refractive Index: 1.5320 (estimate)
  • Water Partition Coefficient: Hydrolyzes in water.
  • PSA: 43.37000
  • LogP: 1.51230
  • Solubility: Not available
  • Sensitiveness: Moisture Sensitive

DL-Camphoric anhydride Security Information

  • WGK Germany:3
  • Hazard Category Code: 22-36/37/38
  • Safety Instruction: S24/25
  • FLUKA BRAND F CODES:10-21
  • Hazardous Material Identification: Xn
  • Safety Term:S24/25
  • Storage Condition:2-8°C
  • Risk Phrases:R22; R36/37/38

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DL-Camphoric anhydride Related Literature

Additional information on DL-Camphoric anhydride

Introduction to DL-Camphoric Anhydride (CAS No. 595-30-2)

DL-Camphoric anhydride, with the chemical name (1R,3S,5S)-3,5-dimethyl-2-(1-methylethyl)-bicyclo[3.1.0]hexane-2-one, is a compound of significant interest in the field of organic chemistry and pharmaceutical research. Its CAS number, 595-30-2, uniquely identifies it in scientific literature and databases, facilitating precise referencing and study. This bicyclic ketone derivative is renowned for its versatile applications, particularly in the synthesis of chiral compounds and as an intermediate in drug development.

The molecular structure of DL-Camphoric anhydride features a camphor-like framework, characterized by a bridged bicyclic system with two methyl groups and an isopropyl group substituents. This configuration imparts unique steric and electronic properties, making it a valuable building block in medicinal chemistry. The compound's ability to exist as a racemic mixture (DL-form) allows researchers to explore both enantiomers, providing insights into stereoselectivity and pharmacological activity.

In recent years, DL-Camphoric anhydride has garnered attention for its role in the synthesis of biologically active molecules. Its rigid bicyclic core serves as a scaffold for constructing complex structures, enabling the development of novel therapeutic agents. For instance, studies have demonstrated its utility in the preparation of protease inhibitors and kinase inhibitors, which are critical targets in oncology and infectious disease treatment. The compound's reactivity also makes it suitable for derivatization into esters, amides, and other functionalized derivatives, further expanding its synthetic potential.

One of the most compelling aspects of DL-Camphoric anhydride is its application in asymmetric synthesis. Researchers have leveraged its chiral center to develop catalytic systems that enhance enantioselectivity in organic transformations. This has led to more efficient routes for producing enantiomerically pure compounds, which are often required for pharmaceutical applications due to their improved efficacy and reduced side effects. The compound's compatibility with various catalytic systems, including transition metal catalysts and biocatalysts, underscores its versatility as a synthetic intermediate.

The pharmaceutical industry has also explored DL-Camphoric anhydride for its potential as a prodrug or adjuvant. Prodrug strategies involve converting a less soluble or inactive drug into a more soluble and bioactive form upon administration. DL-Camphoric anhydride's ability to undergo hydrolysis or other metabolic transformations makes it an attractive candidate for such applications. Additionally, its structural motif has been incorporated into adjuvants designed to enhance immune responses in vaccine formulations.

Recent advances in computational chemistry have further illuminated the utility of DL-Camphoric anhydride. Molecular modeling studies have revealed insights into its interactions with biological targets, aiding in the rational design of drug candidates. These simulations have helped predict binding affinities and optimize molecular structures for improved pharmacokinetic properties. The integration of experimental data with computational methods has provided a more comprehensive understanding of how DL-Camphoric anhydride functions in complex biological systems.

The agrochemical sector has not been left behind in exploring the potential of DL-Camphoric anhydride either. Its structural features make it a viable candidate for developing novel pesticides and herbicides that target specific enzymatic pathways in pests while minimizing environmental impact. By modifying its functional groups or incorporating it into larger molecular frameworks, researchers aim to create compounds that offer enhanced efficacy and selectivity.

Environmental considerations also play a role in the research involving DL-Camphoric anhydride. Efforts are underway to develop greener synthetic routes that reduce waste and energy consumption without compromising yield or purity. These initiatives align with broader trends in sustainable chemistry, emphasizing the importance of environmentally responsible practices in chemical manufacturing.

Despite these advancements, challenges remain in fully harnessing the potential of DL-Camphoric anhydride. Issues such as scalability of synthesis and optimization of reaction conditions are critical areas of focus for industrial applications. Collaborative efforts between academia and industry are essential to address these challenges and translate laboratory discoveries into practical solutions.

In conclusion, DL-Camphoric anhydride (CAS No. 595-30-2) represents a fascinating compound with diverse applications across multiple scientific disciplines. Its unique structural features and reactivity make it indispensable in pharmaceutical research, catalysis, agrochemistry, and environmental science. As our understanding of its properties continues to evolve through interdisciplinary collaboration, DL-Camphoric anhydride is poised to play an even greater role in shaping future advancements.

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