Cas no 39015-77-5 (Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-)

Butanedioic acid, 2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, is a chemically modified derivative of caffeic acid, featuring a succinate ester linkage. This compound combines the antioxidant properties of the catechol moiety with enhanced solubility and stability due to the succinic acid backbone. Its structure allows for improved bioavailability and controlled release in applications such as pharmaceutical formulations and cosmetic antioxidants. The presence of both phenolic hydroxyl groups and a conjugated double bond system contributes to its free radical scavenging activity, making it useful in oxidative stress mitigation. The esterification also broadens its compatibility with hydrophobic matrices, facilitating incorporation into diverse delivery systems.
Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]- structure
39015-77-5 structure
Product Name:Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-
CAS No:39015-77-5
MF:C13H12O8
MW:296.229584693909
CID:297076
PubChem ID:4484594
Update Time:2025-05-20

Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]- Chemical and Physical Properties

Names and Identifiers

    • Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-
    • CAFFEOYLMALIC ACID
    • 2-O-caffeoyl-L-malate
    • Caffeoyl-L-malic acid
    • phaselic acid
    • trans-caffeoyl-L-malic acid
    • 2-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]butanedioic acid
    • Caffeylmalic acid
    • CAFFEOYLMALIC ACID(SH)
    • Butanedioic acid, 2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-
    • Acetylsalicylic Acid Impurity 11(Caffeylmalic acid)
    • Caffeoyimalic acid
    • SCHEMBL3633011
    • Inchi: 1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)
    • InChI Key: PMKQSEYPLQIEAY-UHFFFAOYSA-N
    • SMILES: C(O)(=O)C(OC(=O)C=CC1=CC=C(O)C(O)=C1)CC(O)=O

Computed Properties

  • Exact Mass: 324.08500
  • Monoisotopic Mass: 296.05321734g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 7
  • Complexity: 430
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 1
  • XLogP3: 0.6
  • Topological Polar Surface Area: 141?2

Experimental Properties

  • Density: 1.589±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 557.1±50.0 °C(Predicted)
  • Solubility: Slightly soluble (9.5 g/l) (25 o C),
  • PSA: 119.36000
  • LogP: 1.18810
  • pka: 2.60±0.23(Predicted)

Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]- Security Information

  • Hazardous Material transportation number:NONH for all modes of transport
  • Storage Condition:?20°C

Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]- Pricemore >>

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Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]- Related Literature

Additional information on Butanedioic acid,2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-

Butanedioic Acid, 2-[[3-(3,4-Dihydroxyphenyl)-1-Oxo-2-Propen-1-Yl]Oxy]: A Comprehensive Overview

Butanedioic acid, 2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy], also known by its CAS number 39015-77-5, is a compound of significant interest in the fields of organic chemistry and biochemistry. This compound is characterized by its unique structure, which combines a butanedioic acid backbone with a substituted propenoyl group. The presence of the 3,4-dihydroxyphenyl moiety adds complexity to its chemical profile, making it a subject of extensive research in recent years.

The compound's structure is notable for its conjugated system, which plays a crucial role in its chemical reactivity and biological activity. The dihydroxyphenyl group is particularly interesting due to its potential for participating in hydrogen bonding and aromatic interactions. Recent studies have highlighted the importance of such structural features in determining the compound's stability and bioavailability. For instance, researchers have found that the dihydroxyphenyl group enhances the compound's ability to interact with biological systems, making it a promising candidate for drug development.

In terms of synthesis, Butanedioic acid, 2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy] can be prepared through various routes, including condensation reactions and oxidation processes. One of the most efficient methods involves the reaction of a suitable propenoyl derivative with butanedioic acid under controlled conditions. The optimization of these reaction conditions has been a focus of recent studies, with researchers exploring the use of catalysts and solvents to improve yield and purity.

The compound has shown potential in several applications. In the food industry, it has been investigated as a natural preservative due to its ability to inhibit microbial growth. Its antioxidant properties make it a valuable addition to food formulations aimed at extending shelf life while maintaining nutritional quality. In cosmetics, the compound has been studied for its potential as an antiaging ingredient. Its ability to scavenge free radicals and protect cellular components from oxidative damage has led to its inclusion in skincare products targeting signs of aging.

In the pharmaceutical sector, CAS No 39015-77-5 has garnered attention for its potential therapeutic applications. Preclinical studies have demonstrated its efficacy in reducing inflammation and alleviating symptoms associated with chronic diseases such as arthritis and neurodegenerative disorders. The compound's ability to modulate key signaling pathways involved in inflammation has positioned it as a promising lead compound for drug discovery.

Recent advancements in computational chemistry have further enhanced our understanding of this compound's properties. Molecular docking studies have revealed potential binding sites on target proteins, providing insights into its mechanism of action. Additionally, quantum chemical calculations have shed light on the electronic structure of the molecule, contributing to the development of more accurate predictive models for its behavior in different environments.

In conclusion, Butanedioic acid, 2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-Yl]Oxy], or CAS No 39015-77-5, is a multifaceted compound with diverse applications across various industries. Its unique chemical structure and functional groups endow it with properties that make it valuable in food science, cosmetics, and pharmaceuticals. As research continues to uncover new insights into its potential uses and mechanisms, this compound is poised to play an increasingly important role in advancing scientific and technological innovations.

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