127-25-3Relevant articles and documents
Rosin-based acid anhydrides as alternatives to petrochemical curing agents
Liu, Xiaoqing,Xin, Wenbo,Zhang, Jinwen
, p. 1018 - 1025 (2009)
In this paper, two bio-based epoxy curing agents were synthesized using rosin acids. The chemical structures of the rosin derivatives were confirmed in detail by 1H NMR, 13C NMR, FT-IR and ESI-MS. The synthesis methods of the rosin-based curing agents, curing behaviors and properties of the cured epoxy resins were studied. Two commercial curing agents, which have similar functionality and structural resemblance to the rosin-based curing agents, were also used in the study for comparison. Compared with the synthesis of petrochemical curing agents, the synthesis of rosin-based curing agents was simpler and more environmentally friendly, and has less strict requirements on reactors and catalysts. Non-isothermal curing of a commercial liquid epoxy was studied using differential scanning calorimetry (DSC). The thermal mechanical properties and thermal stability of the cured epoxy resins were evaluated using dynamic mechanical analysis (DMA) and thermogravimetric analysis (TGA), respectively. Results showed that the curing behaviors of the rosin-based curing agents were similar to those of the commercial curing agents. The epoxies cured by rosin-based curing agents also demonstrated similar thermal mechanical properties and thermal stability to the epoxies cured by commercial curing agent analogs.
Cytotoxic, immunomodulatory, antimycotic, and antiviral activities of semisynthetic 14-hydroxyabietane derivatives and triptoquinone C-4 epimers
Zapata, Bibiana,Rojas, Mauricio,Betancur-Galvis, Liliana,Mesa-Arango, Ana Cecilia,Perez-Guaita, David,Gonzalez, Miguel A.
, p. 1239 - 1246 (2013)
A series of C14-hydroxy derivatives of dehydroabietic acid were synthesised from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities. From these C14-hydroxy derivatives, triptoquinone C-4 epimers were obtained and their immunomodulatory activity was additionally evaluated. None of the tested compounds showed antiviral activity against herpes simplex virus type 1 (HHV-1), and nor did they display antimycotic activity against certain Aspergillus, spp. except for one compound, abieta-8,11,13-trien- 14,18-diol. Interestingly, two triptoquinone epimers showed cytotoxic activity, and one of them induced mitochondrial potential loss, DNA damage and cell cycle distribution alterations in Jurkat cells, but not in human peripheral blood mononuclear cells. In addition, these compounds inhibited monocyte's differentiation and production of pro-inflammatory cytokines, IL-1β and TNF-α, and the anti-inflammatory cytokine IL-10 in the presence of LPS. In conclusion, one of the triptoquinone molecules could be a promising scaffold for the development of novel anti-cancer agents, and two of them could be potential anti-inflammatory agents. The Royal Society of Chemistry.
Phytoalexin-like Activity of Abietic Acid and Its Derivatives
Spessard, Gary O.,Matthews, David R.,Nelson, Michael D.,Rajtora, Tim C.,Fossum, Michael J.,Giannini, John L.
, p. 1690 - 1694 (1995)
Abietic acid and some of its derivatives, not known to be naturally occurring phytoalexins, were examined for their ability to promote H+ conductance across membranes and to inhibit growth of two fungal species-Aphanomyces euteiches and Fusarium moniliforme.These results were compared with those of phaseollin, at phytoalexin isolated from kidney beans.Ion leakage and fungal growth inhibition were shown to be a function of structure, results that suggest that pterocarpan phytoalexin activity requires the presence of a polar, protic functional group situated at the end of a large, rigid hydrophobic moiety.Log P values for phaseollin, abietic acid, and some derivatives of abietic acid were also determined. Keywords: Abietic acid; H+ leakage; antifungal activity; log P; phaseollin
Synthesis of new chiral synthons through regioselective ozonolysis of methyl abietate
Dos Santos, Catarina,De Rosso, César R.S.,Imamura, Paulo M.
, p. 1903 - 1910 (1999)
The regioselective ozonolysis of methyl abietate to a stable epoxy- ozonide is described.
Synthesis of complex and diverse compounds through ring distortion of abietic acid
Rafferty, Ryan J.,Hicklin, Robert W.,Maloof, Katherine A.,Hergenrother, Paul J.
, p. 220 - 224 (2014)
Many compound screening collections are populated by members that possess a low degree of structural complexity. In an effort to generate compounds that are both complex and diverse, we have developed a strategy that uses natural products as a starting point for complex molecule synthesis. Herein we apply this complexity-to-diversity approach to abietic acid, an abundant natural product used commercially in paints, varnishes, and lacquers. From abietic acid we synthesize a collection of complex (as assessed by fraction of sp 3-hybridized carbons and number of stereogenic centers) and diverse (as assessed by Tanimoto analysis) small molecules. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens. Abietic acid was used as the starting point for the synthesis of 84 complex and diverse small molecules. Their complexity was assessed by the fraction of sp3-hybridized carbon atoms and the number of stereogenic centers, and their diversity was evaluated by Tanimoto analysis. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens. Copyright
Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
González-Cardenete, Miguel A.,Zaragozá, Ramón J.
, p. 15015 - 15022 (2020/04/27)
The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.
Studies on the [2+3] cycloaddition reaction of nitrile oxides to abietic acid esters
Gucma, Miros?aw,Go??biewski, W. Marek,?elechowski, Krzysztof,Krawczyk, Maria
, p. 1073 - 1081 (2019/11/19)
[2+3] Dipolar cycloadditions of aromatic nitrile oxides to abietic acid esters were investigated. The reactions showed complete site selectivity and regioselectivity, while the stereoselectivity depended on the structures of the dipolarophiles.
