Studies in Waxes. XIV. An Investigation of the Aliphatic Constituents of Hydrolysed Wool Wax by Gas Chromatography

Downing, D. C.; Kranz, ZH; Murray, KE

doi:10.1071/ch9600080

Cited by 128 publications

(30 citation statements)

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“…Interest in epicuticular wax is by no means a new phenomenon. Similar studies of other protective coverings, such as coverings of pollen grains (4), mammalian skin [sheep (5) and man (6)], and arthropodal exoskeleton cuticle [for example, cockroach (7)], are being pursued and are bringing to light interesting similarities and contrasts. Chibnall and his colleagues (3), in the period 1930 to 1950, examined the chemical composition of the waxes by means of fractional crystallizations, precision melting point determinations, and x-ray powder diagrams.…”

Section: Geoffrey Eglinton and Richard J Hamiltonmentioning

confidence: 99%

“…The carboxylic acid fraction can be analyzed by gas-liquid chromatography and mass spectrometry, either as the corresponding methyl esters or after reduction to the saturated hydrocarbons This latter route, which has been well studied by the Commonwealth Scientific and Industrial Research Organization group in Australia (5), has the added advantage that the resulting mixture of alkanes can be cleanly separated into straightand branchedchain alkanes through use of the Linde sieve. The alcohol fraction can be analyzed by gas-liquid chromatography, either as the free alcohols or as their acetates, but it seems likely that the best derivatives will prove to be the trimethyl-silyl ethers, ROSi(CHO) , since they are easily chromatographed and display characteristic mass-spectrometric fragmentation patterns (65 Fig.…”

Section: Chemical Constitutionmentioning

confidence: 99%

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Leaf Epicuticular Waxes

Eglinton

Hamilton²

1967

Science

2,468

1,060

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The external surface of the higher plants comprises a cuticular layer covered by a waxy deposit. This deposit is believed to play a major part in such phenomena as the water balance of plants and the behavior of agricultural sprays. The wax contains a wide range of organic compounds. These complex mixtures are amenable to modern microchromatographic and microspectrometric analytical procedures. The few surveys which have been made of the species distribution of certain classes of constituents indicate that such distribution may be of limited taxonomic value; however, the wax composition of a species may differ for different parts of the same plant and may vary with season, locale, and the age of the plant. This fascinating subject, in which the disciplines of botany, biochemistry, chemistry, and physics overlap and interact, is still in a very active state. Much remains to be learned about the composition and fine structure of the wax deposits, and, for this, experimental study of wax crystallization and permeation through artificial membranes will be required. Enzymic studies, radiolabeling, and electron microscopy will be needed to reveal the mode of biogenesis of the wax constituents and their site of formation and subsequent pathway through the cuticle to the leaf surface.

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Section: Geoffrey Eglinton and Richard J Hamiltonmentioning

confidence: 99%

Section: Chemical Constitutionmentioning

confidence: 99%

Leaf Epicuticular Waxes

Eglinton

Hamilton²

1967

Science

2,468

1,060

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“…The presence of ω ‐hydroxyacids in hydrolysed wool wax may be attributed to epidermal acylceramide and possibly ω ‐hydroxyceramide .…”

Section: Mammalian Epidermal Sphingolipidsmentioning

confidence: 99%

Naturally occurring ω‐Hydroxyacids

Wertz¹

2017

Intern J of Cosmetic Sci

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x-Hydroxyacids are fatty acids bearing a hydroxyl group on the terminal carbon. They are found in mammals and higher plants and are often involved in providing a permeability barrier, the primary purpose of which is to reduce water loss. Some x-hydroxyacid derivatives may be involved in waterproofing and signalling. The purpose of this review was to survey the known natural sources of x-hydroxyacids. x-Hydroxyacids are produced by two different P450-dependent mechanisms. The longer (30-34 carbons) x-hydroxyacids are produced by chain extension from palmitic acid until the chain extends across the membrane in which the extension is taking place, and then the terminal carbon is hydroxylated. Shorter fatty acids can be hydroxylated directly to produce C16 and C18 x-hydroxyacids found in plants and 20-eicosatetraenoic acid (20-HETE) by a different P450. The C16 and C18 x-hydroxyacids are components of polymers in plants. The long-chain x-hydroxyacids are found in epidermal sphingolipids, in giant-ring lactones from the sebum of members of the equidae, as a component of meibum and in carnauba wax and wool wax.R esum e Les x-hydroxyacides sont des acides gras portant un groupe hydroxyle sur le carbone terminal. Ils sont pr esents chez les mammif eres et les plantes sup erieures et sont souvent impliqu es dans les ph enom enes de barri ere de perm eabilit e, dont le but principal est de r eduire la perte d'eau. Certains d eriv es x-hydroxyacides peuvent etre impliqu es dans l'imperm eabilisation et la signalisation. Le but de cette revue est d' etudier les sources naturelles connues de xhydroxyacides. Les H -hydroxyacides sont produits par deux m ecanismes diff erents P450 d ependants. Les x-hydroxyacides plus longs (30 a 34 atomes de carbone) sont produits par extension de la chaîne a partir de l'acide palmitique jusqu' a ce que la chaîne s' etende a travers la membrane dans laquelle l'extension a lieu, puis le carbone terminal est hydroxyl e. Les acides gras plus courts peuventêtre hydroxyl es directement pour produire des x-hydroxyacides en C16 et C18 trouv es dans les plantes et l'acide 20-eicosat etra eno€ ıque (20-HETE) par un P450 diff erent. Les x-hydroxyacides en C16 et C18 sont des composants de polym eres dans les plantes. Les x-hydroxyacides a longue chaîne se trouvent dans les sphingolipides epidermiques, dans des anneaux g eants des lactones provenant du s ebum des equid es, en tant que constituants du meibum et dans la cire de carnauba et la cire de laine.

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“…T HE GAS CHROMATOGRAPHIC ANALYSIS o f the normal paraffins in wool wax was first reported by Downing et aL (1). Recently the paraffinic hydrocarbons of wool wax have been characterized in detail by the investigations of Mold et al (2,3).…”

Section: Introductionmentioning

confidence: 99%

Distribution modes and possible origins of sheep wool hydrocarbons

Simmonds

Nooner

Zlatkis

et al. 1968

J Americ Oil Chem Soc

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An unusual mode of distribution of lowmolecular-weight n-alkanes (Cn-CI~) with a slight even carbon-number predominance has been observed in the gas chromatographic analysis of the paraffin fraction which was extracted from the wool of live sheep. This is in addition to the other two modes of medium-, C15-C2~, and high-, C24-Caa, molecular-weight alkanes usually present in wool wax which have also been found in sheep's manure. The highmolecular-weight hydrocarbons (predominantly odd carbon-numbered) are presumed to be derived from the diet (pasture plants) whereas the other two hydrocarbon distributions probably result from the combined action of animal and microbial metabolism.

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Studies in Waxes. XIV. An Investigation of the Aliphatic Constituents of Hydrolysed Wool Wax by Gas Chromatography

Cited by 128 publications

References 0 publications

Leaf Epicuticular Waxes

Leaf Epicuticular Waxes

Naturally occurring ω‐Hydroxyacids

Distribution modes and possible origins of sheep wool hydrocarbons

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