Solubilities of High Molecular Weight Normal Aliphatic Primary Alcohols

Hoerr, C. W.; Harwood, H. James; Ralston, A. W.

doi:10.1021/jo01185a010

Cited by 26 publications

(13 citation statements)

References 18 publications

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“…termination can be isolated easily by chromatographic techniques. Critical solution temps determined with the micromethod agree in many cases with data reported by authors who had obtained these values through solubility studies (6,(25)(26)(27)(28)47). Deviations can be due to differences in the purity of the preparations analyzed and/or the purity of the test substances used.…”

Section: May 1965supporting

confidence: 85%

Characterization and identification of lipids by their critical solution temperatures

Schmid

Mangold

Lundberg

1965

J Americ Oil Chem Soc

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Section: May 1965supporting

confidence: 85%

Characterization and identification of lipids by their critical solution temperatures

Schmid

Mangold

Lundberg

1965

J Americ Oil Chem Soc

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“…This was confirmed by experiments using shorter chain compounds showing a higher solubility in methanol, e.g. for 1‐decanol (>1310 g 100 mL −1 ) and n ‐decane (8.1 g 100 mL −1 ) at 20 °C . To our knowledge, for higher alcohols and alkanes above 18 carbon atoms, solubility data in methanol have not yet been published.…”

Section: Discussionmentioning

confidence: 63%

“…To our knowledge, for higher alcohols and alkanes above 18 carbon atoms, solubility data in methanol have not yet been published. However, it is clear that a higher hydrocarbon chain length will drastically decrease solubility, as seen with alcohols in the range C 10 (18.8 g 100 mL −1 ) to C 18 (0.3 g 100 mL −1 ) . By contrast, higher solubility in methanol was reported for cyclic triterpenoids like ursolic acid (0.76 g 100 mL −1 ), the main compound of the cyclic wax fraction of P. laurocerasus …”

Section: Discussionmentioning

confidence: 99%

The permeation barrier of plant cuticles: uptake of active ingredients is limited by very long‐chain aliphatic rather than cyclic wax compounds

Staiger

Seufert

Arand

et al. 2019

Pest Management Science

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BACKGROUND The barrier to diffusion of organic solutes across the plant cuticle is composed of waxes consisting of very long‐chain aliphatic (VLCA) and, to varying degrees, cyclic compounds like pentacyclic triterpenoids. The roles of both fractions in controlling cuticular penetration by organic solutes, e.g. the active ingredients (AI) of pesticides, are unknown to date. We studied the permeability of isolated leaf cuticular membranes from Garcinia xanthochymus and Prunus laurocerasus for lipophilic azoxystrobin and theobromine as model compounds for hydrophilic AIs. RESULTS The wax of P. laurocerasus consists of VLCA (12%) and cyclic compounds (88%), whereas VLCAs make up 97% of the wax of G. xanthochymus. We show that treating isolated cuticles with methanol almost quantitatively releases the cyclic fraction while leaving the VLCA fraction essentially intact. All VLCAs were subsequently removed using chloroform. In both species, the permeance of the two model compounds did not change significantly after methanol treatment, whereas chloroform extraction had a large effect on organic solute permeability. CONCLUSION The VLCA wax fraction makes up the permeability barrier for organic solutes, whereas cyclic compounds even in high amounts have a negligible role. This is of significance when optimizing the foliar uptake of pesticides. © 2019 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

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“…Nevertheless, as the overall 1:3 polymer: wax ratio is rather close to that of pure wax, it is not surprising that the observed transformation temperature is close to the wax melting point; although no data were found for the EC: C18E0 system, solubility studies of the higher 1-alkanols in many solvents (Domań ska and Gonzalez, 1997;Hoerr et al, 1944) indicate, especially for the long alcohols such as C18E0, a rather flat liquidus curve near the pure alcohol. This also suggests a rather sharp -if not strictly at a single temperature -phase transformation behaviour, i.e.…”

Section: Correlation With Phase Behaviourmentioning

confidence: 98%