1446-61-3

Usage

Uses

Used in Pharmaceutical Industry:
Dehydroabietylamine is used as an active pharmaceutical ingredient for its broad-spectrum antibiotic effect. It is effective against various bacterial strains such as Staphylococcus p.a. (sic), Escherichia coli, and Mycobacterium tuberculosis, as well as the fungal pathogen Candida albicans. Its potent antibiotic activity makes it a valuable compound in the development of new drugs to combat resistant infections.
Used in Antimicrobial Applications:
In the field of antimicrobial agents, Dehydroabietylamine serves as a key component in the formulation of products designed to inhibit the growth of harmful microorganisms. Its broad-spectrum activity allows for its use in various applications, including medical, industrial, and consumer products, to ensure cleanliness and prevent the spread of infections.
Used in Research and Development:
Dehydroabietylamine is also utilized in research and development for the discovery and creation of new antibiotics and antimicrobial compounds. Its unique properties and effectiveness against a wide range of pathogens make it an important tool in the ongoing fight against antibiotic resistance and the development of novel treatments for infectious diseases.

Biological Activity

CB 1 agonist. Displaces binding of [ 3 H]-SR141716A with an IC 50 value of 2.86 μ M.

Purification Methods

The crude base is purified by converting 2g of base in toluene (3.3mL) into the acetate salt by heating at 65-70o with 0.46g of AcOH, and the crystals are collected and dried (0.96g from two crops, m 141-143o). The acetate salt is dissolved in warm H2O, basified with aqueous NaOH and extracted with *C6H6. The dried extract (MgSO4) is evaporated in vacuum leaving a viscous oil which crystallises and can be distilled. [Gottstein & Cheney J Org Chem 30 2072 1965.] The picrate has m 234-236o (from aqueous MeOH), and the formate has m 147-148o (from heptane). [Beilstein 12 IV 3005.]

InChI:InChI=1/C20H31N/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18H,5,7,9-11,13,21H2,1-4H3/p+1/t18-,19-,20+/m0/s1

Upstream product

• 31148-95-5 (+)-dehydroabietylnitrile 
• 471-77-2 neoabietic acid 
• 514-10-3 abietic acid 
• 22478-66-6 dehydroabietic acid chloride 
• 35928-32-6 (1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxamide 
• 2026-24-6 (+)-dehydroabietylamine acetate 
• 1740-19-8 dehydroabietic acid 
• 141666-88-8 N-Dehydroabietyl-p-toluenesulfonamide 

Downstream Products

• 125-92-8 bisdehydroabietylamino-N¹,N²-ethane-1,2-diamine 
• 132427-78-2 3-((1,4a-dimethyl-7-(1-methylethyl)-1,2,3,4,4a,9,10,10a-octahydro-1-phenanthrenyl)methylamino)-1-(4-fluorophenyl)-1-propanone 
• 104265-84-1 C-((1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-methylamine; compound with (1S,2R)-cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester 
• 104265-85-2 C-((1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-methylamine; compound with (1R,2S)-cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester 
• 1194046-24-6 dehydroabietylamine m-fluorobenzaldehyde imine 
• 1355345-79-7 C₂₇H₃₂ClNO₂ 
• 1413803-04-9 C₂₇H₃₂N₂O₄ 
• 1413803-10-7 N-(o-chlorobenzoyl)-12-nitrodehydroabietylamine 
• 1413803-13-0 N-(p-nitrobenzoyl)-12-nitrodehydroabietylamine 
• 35060-20-9 N-(((1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)benzamide 
• 1355345-78-6 N-(o-chlorobenzoyl)dehydroabietylamine 
• 1413802-97-7 N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-nitrobenzamide 
• 1207530-29-7 N-(5-bromo-salicylaldehyde)dehydroabietylamine 

Relevant academic research and scientific papers

Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection

In the current work, we synthesized two series of dehydroabietyl amide derivatives from natural product rosin and evaluated their antifungal effects on Valsa mali, Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, and Fusarium oxysporum. In vitro and in vivo antifungal activities results indicated that rosin-based amide compounds containing thiophene heterocycles had better inhibitory effects on B. cinerea. In particular, compound 5b (5-fluoro-2-thiophene dehydroabietyl amide) exhibited the excellent antifungal properties against B. cinerea with an EC50 of 0.490 mg/L, which was lower compared to the positive control penthiopyrad (0.562 mg/L). Physiological and biochemical studies showed that the primary action mechanism of compound 5b on B. cinerea changes mycelial morphology, increases cell membrane permeability, and inhibits the TCA pathway in respiratory metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable biological activity.

Sulfoxide ligand metal catalyzed oxidation of olefins

The enantioselective synthesis of isochroman motifs has been accomplished via Pd(II)-catalyzed allylic C—H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C—H oxidation reaction proceeds with the broadest scope and highest levels asymmetric induction reported to date (avg. 92% ee, 13 examples ≥90% ee). Additionally, C(sp3)-N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) catalyzed intermolecular allylic C—H amination is disclosed. A range of 52 allylic amines are furnished in good yields (avg. 76%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). For the first time, a variety of singly activated aromatic and aliphatic nitrogen nucleophiles, including ones with stereochemical elements, can be used in fragment coupling stiochiometries for intermolecular C—H amination reactions.

1-(1)-dehydroabietylimidazolium salts as enantiomer discriminators for NMR spectroscopy

Nine new (+)-dehydroabietylimidazolium salts were synthesised and studied as chiral solvating agents for several different racemic aromatic and non-aromatic carboxylate salts. These cationic chiral solvating agents resolve racemic ionic analytes better than non-ionic ones. Bis(dehydroabietylimidazolium) bis(trifluoromethanesulfonimide) gave the best discrimination for the enantiomers of carboxylate salts. Its resolution behaviour was studied by an NMR titration experiment, which indicated 1 : 1 complexation with the racemic analyte. The dehydroabietylimidazolium salts were also useful in enantiomeric excess (ee) determinations, and for the recognition of chirality of racemic aromatic and nonaromatic a-substituted carboxylic acids.

Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation

The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene (4 mol %) in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective.

Chiral stationary phases and columns for chromatographic resolution

This invention relates to chiral compositions.

Dehydroabietylammonium salts of 6-oxo-2-piperidinecarboxylic acid

6-Oxo-2-piperidinecarboxylic acid has been resolved via direct crystallization of pure S-6-oxo-2-piperidinecarboxylic acid dehydroabietylammonium salt from a solvent system consisting of dimethylformamide, cyclohexane and acetone. The S-enantiomer is a required component for making certain tripeptides related to thyrotropin releasing hormone (TRH) which are central nervous system stimulants.