24563-92-6

Upstream product

• 514-10-3 (?)-abietic acid 
• 74-88-4 methyl iodide 
• 514-10-3 (?)-abietic acid 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 17817-95-7 7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid 

Downstream Products

• 3513-69-7 methyl sapietate 
• 28625-40-3 methyl (1R,4aS,10aR)-6-acetyl-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenantrene-1-carboxylate 
• 13742-23-9 (1R,4aS,10aR)-6-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 
• 22595-48-8 18-Hydroxyferruginol 
• 1235-74-1 Methyl dehydroabietate 
• 55623-34-2 (1R,4aR)-7-Isopropyl-1,4a-dimethyl-6-oxo-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid methyl ester 
• 13742-23-9 (1R,4aS)-6-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 
• 1235-74-1 methyl dehydroabietate 
• 13082-81-0 9-α-hydroxy-abietic acid methyl ester 
• 1802-09-1 (1R,4aS,9S)-9-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 
• 1802-09-1 (1R,4aS,9R)-9-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 
• 5395-88-0 7-keto dehydroabietic acid methyl ester 
• 89288-45-9 (1R,4aS)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

In depth analysis of chiroptical properties of enones derived from abietic acid

With the use of inexpensive commercially available abietic acid, a whole series of abietane enones were prepared in high yields. The structures of all the products obtained were determined by comprehensive spectroscopic analysis with particular emphasis on the use of advanced NMR techniques, comparison with previously reported data and, where possible, by single crystal X-ray diffraction. However, in cases where X-ray crystallography was not applicable or compounds tested were unstable, a final stereochemical assignment could be inferred only by electronic circular dichroism (ECD) supported by vibrational circular dichroism to increase credibility. To reveal the relationship between structure and chiroptical properties, we used combined experimental and theoretical analysis of geometries, structural parameters, and chiroptical properties of all enones synthesized. A thorough analysis of their conformational flexibility by examining the effect of solvent and temperature on the ECD spectra was also used to achieve desired objectives. As a result, the impact of substituents adjacent to the enone chromophore on the conformation was determined by demonstrating that even slight changes in the position of hydroxyl and isopropyl groups attached to carbon C13 may substantially affect ECD curves' pattern, leading in some cases to Cotton effects sign reversal.

Synthesis of 4- epi-Parviflorons A, C, and E: Structure-Activity Relationship Study of Antiproliferative Abietane Derivatives

The first syntheses of 4-epi-parviflorons A, C, and E (4-epi-1-3) were achieved in 12-13 steps from commercially available (-)-abietic acid (5). All synthesized compounds, including intermediates and derivatives, were evaluated for antiproliferative activity against five human tumor cell lines. A structure-activity relationship study revealed no significant difference between Pf E and 4-epi-Pf E, the importance of two oxygen functional groups at C-11 and C-12 for antiproliferative activity, as well as a combination of carbomethoxy at C-4 and a benzoyl ester with electron-drawing group at C-12 or hydroxymethyl at C-4 and an appropriate oxidation state of ring-B/C for triple-negative breast cancer cell selectivity.

Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies

The first semisynthesis and biological profiling of the new abietane diterpenoid (+)-liquiditerpenoic acid A (abietopinoic acid) (7) along with several analogues are reported. The compounds were obtained from readily available methyl dehydroabietate (8), which was derived from (-)-abietic acid (1). Biological comparison was conducted according to the different functional groups, leading to some basic structure-activity relationships (SAR). In particular, the ferruginol and sugiol analogues 7 and 10-16 were characterized by the presence of an acetylated phenolic moiety, an oxidized C-7 as a carbonyl, and a different functional group at C-18 (methoxycarbonyl, carboxylic acid, and hydroxymethyl). The biological properties of these compounds were investigated against a panel of six representative human tumor solid cells (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), five leukemia cellular models (NALM-06, KOPN-8, SUP-B15, UoCB1, and BCR-ABL), and four Leishmania species (L. infantum, L. donovani, L. amazonensis, and L. guyanensis). A molecular docking study pointed out some targets in these Leishmania species. In addition, the ability of the compounds to modulate GABAA receptors (α1β2γ2s) is also reported. The combined findings indicate that these abietane diterpenoids offer a source of novel bioactive molecules with promising pharmacological properties from cheap chiral-pool building blocks.

ROSIN DERIVED EPOXIDES AND CURING AGENTS

An epoxide agent for an epoxy resin system, the epoxide agent comprising at least one non-acid functional rosin moiety and at least one epoxide moiety. Another embodiment is a curing agent for an epoxy resin system comprising at least one non- acid functional rosin moiety and at least one moiety that is reactive with an epoxy.