Cas no 490-20-0 (α-Truxillic acid)

α-Truxillic acid is a cyclic dimer of cinnamic acid, characterized by its unique truxillic framework consisting of two cyclobutane rings. This compound is of interest in organic synthesis and materials science due to its rigid, planar structure, which facilitates stereospecific reactions and serves as a building block for complex molecular architectures. Its photochemical formation via [2+2] cycloaddition offers controlled pathways for polymer and crystal engineering. α-Truxillic acid exhibits stability under standard conditions, making it suitable for research applications requiring precise geometric constraints. Its derivatives are explored in pharmaceuticals and optoelectronics, leveraging its structural predictability and functionalization potential.
α-Truxillic acid structure
α-Truxillic acid structure
Product Name:α-Truxillic acid
CAS No:490-20-0
MF:C18H16O4
MW:296.317245483398
MDL:MFCD00157048
CID:333769
PubChem ID:78213
Update Time:2025-05-25

α-Truxillic acid Chemical and Physical Properties

Names and Identifiers

    • 1,3-Cyclobutanedicarboxylicacid, 2,4-diphenyl-, (1a,2a,3b,4b)-
    • 2,4-diphenylcyclobutane-1,3-dicarboxylic acid
    • 2β,4α-Diphenyl-1β,3α-cyclobutanedicarboxylic acid
    • α-Truxillic Acid
    • 1,3-Cyclobutanedicarboxylicacid, 2,4-diphenyl-, cis-1,2,trans-1,3,trans-1,4- (8CI)
    • a-Truxillic acid
    • Gratissimic acid
    • ??-Truxillic acid
    • Truxillic acid alpha-isomer
    • Q6172554
    • SCHEMBL15590565
    • NSC 103001
    • NS00031446
    • SCHEMBL3482620
    • SCHEMBL21120223
    • IDI1_019387
    • 821BB4R21V
    • AB01330753-02
    • NSC-103001
    • 2beta,4alpha-Diphenyl-1beta,3alpha-cyclobutanedicarboxylic acid
    • FT-0600226
    • MS-24244
    • SCHEMBL20614651
    • rel-(1R,2R,3S,4S)-2,4-Diphenylcyclobutane-1,3-dicarboxylic acid
    • SCHEMBL20598122
    • NCGC00172589-02
    • CBDivE_013278
    • TRUXILLIC ACID .ALPHA.-ISOMER
    • 1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, (1alpha,2alpha,3beta,4beta)-
    • Truxillic acid, alpha-isomer
    • CCG-103288
    • SR-01000078302
    • Q27269288
    • CHEMBL1098368
    • AKOS040732416
    • 490-20-0
    • Truxillic acid alpha-isomer [MI]
    • Truxillic acid
    • CS-0064284
    • 2,4-Diphenyl-cyclobutane-1,3-dicarboxylic acid
    • HMS1473D03
    • CHEMBL4277988
    • DTXSID20196252
    • DTXSID501316746
    • 1,3-diphenylcyclobutane-2,4-dicarboxylic
    • HY-114771
    • 1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-
    • NCGC00172589-01
    • ChemDiv3_000069
    • 2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid
    • 1,3-CYCLOBUTANEDICARBOXYLIC ACID, 2,4-DIPHENYL-, (1.ALPHA.,2.ALPHA.,3.BETA.,4.BETA.)-
    • BDBM50468455
    • .ALPHA.-TRUXILLIC ACID
    • alpha-Truxillic Acid
    • NSC103001
    • Cocaic acid
    • EINECS 224-724-3
    • Oprea1_453209
    • QWFRRFLKWRIKSZ-UHFFFAOYSA-N
    • AKOS001483772
    • TRUXILLIC ACID [MI]
    • SCHEMBL18674152
    • SCHEMBL4560501
    • SR-01000078302-1
    • 4462-95-7
    • 2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid #
    • TRUXILLIC ACID, .ALPHA.-ISOMER
    • UNII-821BB4R21V
    • α-Truxillic acid
    • MDL: MFCD00157048
    • Inchi: 1S/C18H16O4/c19-17(20)15-13(11-7-3-1-4-8-11)16(18(21)22)14(15)12-9-5-2-6-10-12/h1-10,13-16H,(H,19,20)(H,21,22)
    • InChI Key: QWFRRFLKWRIKSZ-UHFFFAOYSA-N
    • SMILES: OC(C1C(C2C=CC=CC=2)C(C(=O)O)C1C1C=CC=CC=1)=O

Computed Properties

  • Exact Mass: 296.10488
  • Monoisotopic Mass: 296.105
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 4
  • Complexity: 369
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 74.6A^2
  • XLogP3: 2.6

Experimental Properties

  • Color/Form: Solid
  • Density: 1.3±0.1 g/cm3
  • Melting Point: 228.0 °C
  • Boiling Point: 470.5±45.0 °C at 760 mmHg
  • Flash Point: 252.4±25.2 °C
  • Refractive Index: 1.629
  • PSA: 74.6
  • Vapor Pressure: 0.0±1.2 mmHg at 25°C

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Additional information on α-Truxillic acid

α-Truxillic Acid: A Comprehensive Overview

α-Truxillic acid, also known by its CAS number 490-20-0, is a naturally occurring compound that has garnered significant attention in recent years due to its unique chemical properties and potential applications in various fields. This article provides an in-depth exploration of α-Truxillic acid, including its structure, sources, biological activities, and the latest research findings.

The chemical structure of α-Truxillic acid is characterized by a tricyclic system, which contributes to its stability and bioactivity. This compound belongs to the class of triterpenoids, a group of organic compounds that are widely found in plants and exhibit diverse pharmacological effects. Recent studies have highlighted the potential of α-Truxillic acid as a bioactive agent with antioxidant, anti-inflammatory, and anticancer properties.

α-Truxillic acid is primarily isolated from the roots of *Dioscorea truxillensis*, a plant species native to certain regions of South America. Traditional healers have long recognized the medicinal value of this plant, and modern science is now beginning to unravel the molecular mechanisms behind its therapeutic effects. Researchers have employed advanced techniques such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy to characterize α-Truxillic acid and understand its role in biological systems.

One of the most promising areas of research on α-Truxillic acid is its potential as an anticancer agent. Preclinical studies have demonstrated that this compound can induce apoptosis in various cancer cell lines, including breast, colon, and liver cancer cells. The mechanism underlying this activity involves the modulation of key signaling pathways such as MAPK/ERK and PI3K/AKT, which are critical for cell proliferation and survival. These findings suggest that α-Truxillic acid could serve as a novel chemotherapeutic agent or adjuvant therapy for cancer treatment.

In addition to its anticancer properties, α-Truxillic acid has also been investigated for its anti-inflammatory effects. Chronic inflammation is a major contributor to numerous diseases, including cardiovascular disorders, diabetes, and neurodegenerative conditions. Experimental models have shown that α-Truxillic acid can inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6, thereby reducing inflammation-associated tissue damage. These results underscore the potential of α-Truxillic acid as a natural anti-inflammatory agent with applications in chronic disease management.

The antioxidant activity of α-Truxillic acid is another area of active research. Oxidative stress, caused by an imbalance between reactive oxygen species (ROS) and antioxidants, is implicated in aging and various pathological conditions. Studies have demonstrated that α-Truxillic acid can scavenge ROS and enhance the activity of endogenous antioxidant enzymes such as superoxide dismutase (SOD) and catalase (CAT). These properties make it a candidate for inclusion in functional foods or nutraceuticals aimed at improving oxidative stress resistance.

Recent advancements in synthetic chemistry have enabled researchers to explore the total synthesis of α-Truxillic acid, which could facilitate large-scale production for pharmaceutical purposes. Various synthetic routes have been proposed, including biomimetic approaches inspired by natural biosynthesis pathways. These efforts are driven by the need for consistent supply and cost-effective production of this valuable compound.

In conclusion, α-Truxillic acid (CAS 490-20-0) is a multifaceted natural compound with significant potential in medicine and health sciences. Its diverse biological activities, coupled with ongoing research into its mechanisms of action and synthetic routes, position it as a promising candidate for drug development. As scientific understanding of this compound continues to grow, it is likely that new applications will emerge, further solidifying its importance in contemporary pharmacology.

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