Octanohydroxamic Acid Chemical Properties

Melting point:

78°C

Density 

0.970

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.56±0.20(Predicted)

color 

White to Off-White

InChI

InChI=1S/C8H17NO2/c1-2-3-4-5-6-7-8(10)9-11/h11H,2-7H2,1H3,(H,9,10)

InChIKey

RGUVUPQQFXCJFC-UHFFFAOYSA-N

SMILES

C(NO)(=O)CCCCCCC

EPA Substance Registry System

Octanamide, N-hydroxy- (7377-03-9)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RTECS 

RG9900500

HS Code 

2928.00.5000

Octanohydroxamic Acid Usage And Synthesis

Description

Octanohydroxamic acid (OHA), the more common hydroxamate collector, has both an acid group (single bondNHOH) and basic group (single bond CO). The hydrogen in the acid group can be replaced by a metal ion and a dative bond from the basic group to form a chelate. Improved monazite flotation performance was reported when using OHA compared to the results obtained with sodium oleate. Flotation separation of monazite and calcite using OHA has been described in previous publications. OHA was the most potent urease inhibitor among saturated hydroxamic acid (HAs) with a calculated IC50 of 0.25?±?0.1?mM compared to 8.67?±?1.3 and 0.50?±?0.2?mM for Acetohydroxamic acid and heptanohydroxamic acid, respectively. Further increase in the chain length from 8 to 12 carbons negatively affected the potency of HAs[1].

Uses

Octanohydroxamic Acid is used in preparation of Caprylohydroxamic Acid.

Synthesis

To a 1000 mL four-necked flask was added hydroxylamine hydrochloride (48.7 g, 0.70 mol, 1.4 eq.), water (50 g), and ethanol (200 g, 2.3 times the volume), and stirred at room temperature until hydroxylamine hydrochloride was completely dissolved. Ethyl octanoate (86.7 g, 0.5 mol, 1.0 eq.) was then added and stirred at room temperature to form a two-phase system. The reaction mixture was cooled to 5-10°C and 40% KOH solution (168 g, 1.2 mol, 2.4 eq.) was added slowly and dropwise. After the dropwise addition, the reaction system was heated to 50~55°C and the reaction was held for 3 hours and monitored by gas chromatography (GC) until the ethyl octanoate material completely disappeared. After the reaction was completed, cooled to 5~10°C, slowly added concentrated hydrochloric acid (90 mL) to adjust the pH to 6.4~6.7, at which time a large amount of white solid precipitated. The solid was collected by filtration and dried at 50°C for 8 hours. The crude product was recrystallized with benzene to give 78.8 g of white flocculent solid in 91.1% yield.

References

[1] Diana Evstafeva. “Inhibition of urease-mediated ammonia production by 2-octynohydroxamic acid in hepatic encephalopathy.” Nature Communications 15 1 (2024): 2226.

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