DEHYDROABIETYLAMINE Chemical Properties

Melting point:

44.50℃

Boiling point:

417.89°C (rough estimate)

Density 

0.963±0.06 g/cm3 (20 ºC 760 Torr)

refractive index 

n20/D 1.546(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, DMSO, Methanol

form 

White solid.

pka

10.13±0.29(Predicted)

color 

Pale Yellow

optical activity

[α]20/D +56.1°, c = 2.4 in pyridine

BRN 

3084620

InChI

InChI=1S/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/t18-,19-,20+/m0/s1

InChIKey

JVVXZOOGOGPDRZ-SLFFLAALSA-N

SMILES

[C@@]1(C)(CN)[C@@]2([H])[C@@](C)(C3=C(CC2)C=C(C(C)C)C=C3)CCC1

CAS DataBase Reference

1446-61-3(CAS DataBase Reference)

EPA Substance Registry System

Dehydroabietylamine (1446-61-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

TP8701000

F 

10-23

HS Code 

29214990

Hazardous Substances Data

1446-61-3(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

DEHYDROABIETYLAMINE Usage And Synthesis

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.

Definition

ChEBI: [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine is a diterpenoid.

Biological Activity

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

Synthesis

The general procedure for the synthesis of dehydroabietic amine from dehydroabietic amine acetate was as follows: crude 60% (+)-dehydroabietic amine (42.0 g) was dissolved in toluene (70.0 cm3) and a toluene (30.0 cm3) solution of acetic acid (9.65 g) was slowly added. The mixture was crystallized in a refrigerator. The product was collected by filtration and washed with hexane (30.0 cm3). The (+)-dehydrofiramine ethanol compound was recrystallized from methanol. (+)-Dehydrofiramine acetate (21.0 g) was dissolved in hot water and 10% NaOH aqueous solution (28.0 cm3) was added. The (+)-dehydrofiramine was extracted with diethyl ether (50.0 cm3) and the organic phase was washed with water to neutrality and subsequently dried over anhydrous sodium sulfate. The solvent was evaporated and the (+)-dehydrofiramine obtained was dried in vacuum to give a white solid; yield 37.0 g, 88.2%; melting point 44.28 °C (literature value 44-45 °C [16]). [α]22D +44.3480 (c, 10.0 mg/cm3, CHCl?).1H NMR (500 MHz, CDCl?) δ 0.89 (s, 3H, CH?), 1.22 (s, 3H, CH?), 1.22 (d, J=7.0 Hz, 6H, 2 × CH?), 1.33 (m, 2H, CH?), 1.39 ( m, 1H, CHH), 1.52 (dd, J=11.8,3.3Hz, 1H, CH), 1.69 (m, 2H, CH?), 1.74 (m, 2H, CH?), 2.30 (dt, J=13.1,1.7Hz, 1H, CHH), 2.40 (d, J=13.5Hz, 1H, CHH), 2.61 (d, J= 13.5 Hz, 1H, CHH), 2.82 (sep, J=7.0 Hz, CH), 2.88 (m, 2H, CH?), 6.89 (d, J=1.9 Hz, 1H, CHAr), 7.00 (dd, J=8.1,1.9 Hz, 1H, CHAr), 7.18 (d, J=8.1 Hz, 1H, CHAr). 13C NMR (500 MHz, CDCl?) δ 18.78 (CH?), 18.90 (CH?), 18.90 (CH?), 24.11 (CH?), 24.13 (CH?), 25.37 (CH?), 30.31 (CH?), 33.58 (CH), 35.36 (CH?), 37.36 (C). 37.53 (C), 38.70 (CH?), 45.00 (CH), 53.99 (CH?), 123.96 (CHAr), 124.38 (CHAr), 126.94 (CHAr), 134.84 (CAr), 145.67 (CAr), 147.63 (CAr).HRMS-ESI m/z 286.2540; C??H??N [M+H]? Calculated value 286.2529.

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.]

References

[1] Australian Journal of Chemistry, 2017, vol. 70, # 7, p. 845 - 856

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