1446-61-3

Basic information

• Product Name: DEHYDROABIETYLAMINE
• Synonyms: (+)-DEHYDROABIETYLAMINE;DEHYDROABIETYLAMINE;(+)-DEHYDROABIETHYLAMINE;DEHYDROABIETHYLAMINE;D(+)-DEHYDROABIETYLAMINE;LYLAMINE HYDROCHLORIDE;(1R,4AS,10AR)-1,2,3,4,4A,9,10,10A-OCTAHYDRO-1-,4A-DIMETHYL-7-(1-METHYLETHYL)-1-PHENANTHRENEMETHANAMINE HYDROCHLORIDE;1,4A-DIMETHYL-7-ISOPROPYL-1,2,3,4,4A,9,10,10A-OCTAHYDRO-1-PHENANTHRENEMETHYLAMINE
• CAS NO: 1446-61-3
• Molecular Formula: C₂₀H₃₁N
• Molecular Weight: 285.47
• EINECS: 215-899-7
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Antifungal
• Mol File: 1446-61-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 44.50℃
• Boiling Point: 417.89°C (rough estimate)
• Flash Point: >230 °F
• Appearance: clear yellow viscous liquid
• Density: 0.963±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 4.59E-06mmHg at 25°C
• Refractive Index: n20/D 1.546(lit.)
• Storage Temp.: Desiccate at +4°C
• Solubility: Chloroform, DMSO, Methanol
• PKA: 10.13±0.29(Predicted)
• BRN: 3084620
• CAS DataBase Reference: DEHYDROABIETYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: DEHYDROABIETYLAMINE(1446-61-3)
• EPA Substance Registry System: DEHYDROABIETYLAMINE(1446-61-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: TP8701000
• F: 10-23
• Hazardous Substances Data: 1446-61-3(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow viscous liquid

Uses

Dehydroabiethylamine is a primary amine with high molecular weight; shows a strong antibiotic effect with a broad spectrum of activity against Staphylococcus p.a. (sic), Escherichia coli, Mycobacterium tuberculosis, and Candida albicans.

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

• 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 
• 1740-19-8 dehydroabietic acid 
• 141666-88-8 N-Dehydroabietyl-p-toluenesulfonamide 
• 31148-95-5 (+)-dehydroabietylnitrile 
• 2026-24-6 (+)-dehydroabietylamine acetate 

Downstream Products

• 125-92-8 bisdehydroabietylamino-N¹,N²-ethane-1,2-diamine 
• 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 
• 936737-59-6 2-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)isoindoline-1,3-dione 
• 1022186-28-2 C₂₇H₃₄NF 
• 1050442-13-1 C₂₇H₃₄N₂O₃ 
• 1050442-14-2 C₂₇H₃₄NOCl 
• 93591-07-2 dehydroabietylamine benzaldehyde imine 
• 1050442-11-9 C₂₈H₃₇NO 
• 1050442-12-0 C₂₇H₃₄NCl 
• 727396-20-5 4-bromo-1-dehydroabietylamino-2-nitrobenzene 
• 1338604-96-8 5-nitrosalicylidene dehydroabietylamine 
• 1207530-28-6 5-chlorosalicylidene dehydroabietylamine 
• 1338604-95-7 5-bromosalicylidene dehydroabietylamine 

Relevant articles and documents

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.

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.

Chiral stationary phases and columns for chromatographic resolution

This invention relates to chiral compositions.