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.
Efficient syntheis of the key intermediate triptophenolide methyl ether for the synthesis of(-)-triptolide
Zhou, Bing,Li, Xiaomei,Feng, Huijin,Li, Yuanchao
, p. 5396 - 5401 (2010)
An efficient synthesis of triptophenolide methyl ether 4 from the readily available abietic acid 3 in nine steps is described and successfully applied to the synthesis of (-)-triptolide 1.The route is of characteristic of low cost, high yield and easy operation.In addition, every reaction in this route has been successfully scaled-up to a 100 g substrate level without loss of yield.
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.
Research into the oxidation of abietic acid–derived enone with atmospheric oxygen
Masnyk, Marek,Ku?mirek, Damian,Trzybiński, Damian,Frelek, Jadwiga
, p. 437 - 445 (2020)
This work presents results of methyl 7-oxoabiet-13(14)-en-18-oate (3) self-oxidation with air-oxygen in the presence of various bases such as triethylamine or sodium t-butoxide. While under aerobic conditions, the use of sodium t-butoxide as a base results in the formation of four isomeric alcohols, an addition of triethylamine into reaction medium directs the enone 3 oxidation to hydroperoxides. To clarify this base dependence and to obtain more in-depth information about this reaction additional studies with cyclohexenone as a reference enone have been undertaken. Their results demonstrated the predisposition of abietane hydroperoxides to oxidize α,β-unsaturated ketones to epoxides in the presence of t-butoxide while reducing the hydroperoxide group to hydroxyl. This ability of hydroperoxides to epoxidize conjugated double bonds and confirmed by the present study intermolecular course allowed proposing a plausible mechanism for this reaction.
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 and biological evaluation of abietic acid derivatives
Gonzalez, Miguel A.,Correa-Royero, Julieth,Agudelo, Lee,Mesa, Ana,Betancur-Galvis, Liliana
, p. 2468 - 2472 (2009)
A series of C18-oxygenated derivatives of abietic acid were synthesized and evaluated for their cytotoxic, antimycotic, and antiviral activities. In general, the introduction of an aldehyde group at C18 did improve the resultant bioactivity, while the presence of an acid or alcohol led to less active compounds.
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.
Identification of 15-hydroperoxyabietic acid as a contact allergen in Portuguese colophony
Karlberg,Bohlinder,Boman,Hacksell,Hermansson,Jacobsson,Nilsson
, p. 42 - 47 (1988)
15-Hydroperoxyabietic acid (15-HPA) has been isolated from Portuguese colophony of the gum rosin type and identified as its methyl ester. The structure of the compound was elucidated using UV, IR, NMR and mass sepctrometry. 15-HPA methyl ester was found to be an elicitor when tested in colophony-sensitized guinea-pigs. The sensitizing capacity was verified in the same species and 15-HPA methyl ester was considered to be a strong allergen. The eliciting potential was also verified in patients with known allergy to colophony. The Portuguese gum rosin investigated contained approximately 1% of 15-HPA. Based on its allergenicity and the amounts isolated, we conclude that 15-HPA is a main contact allergen in Portuguese gum rosin.
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
A New Synthesis of Desmethylambraoxide
Buchbauer, Gerhard,Heneis, Vera M.,Krejci, Viktoria,Talsky, Claudia,Wunderer, Hanneliese
, p. 1345 - 1358 (1985)
A new synthesis of the title compound starting from abietic acid is described.Regioselective osmylation of the Δ13,14-double bond of abietic acid methyl ester (6) and subsequent hydrogenation furnishes dihydrodihydroxyabietic acid methyl ester (12) with an all-trans-connection of the three rings.Periodate cleavage of 12 leads to 13 which can be transformed into the triester 14 by Baeyer-Villiger oxidation.The configuration of the aldehyde group in 13 as well of the formyloxy group in 14 has been ensured to be equatorial.LAH-reduction of 14 leads to the triol 16 which after cyclisation and reductive dehydroxylation furnishes the fragrance compound 4. - Keywords: Abietic acid; Ambergris fragrance compound; Baeyer-Villiger oxidation; Decahydro-1-naphthalene-carboxylic acid derivatives; Dodecahydro-1H-naphthopyrane derivatives; Periodate cleavage; Reductive dehydroxylation; Regioselective osmylation
