The hydroxy acids of cottonseed oil

It has been established that the oil of the ripe seeds of the cotton plant of variety 108-F contains 9,10-epoxyoctadec-cis-12-enoic (I) and 12,13-epoxyoctadec-cis-9-enoic (II) acids. In addition, 9-hydroxyoctadecacis,trans-10,12-dienoic (III) and 13-hydroxyoctadeca-cis,trans-9,11-dienoic (IV) acids, found previously in other oils, have been detected.     

A mass-spectrometric study of the hydroxy acids of cottonseed oil

Eight new components of the hydoxy acids have been found in the seed oil of the cotton plant of variety Tashkent 1: six monohydroxy acids, of which three are isomeric hydroxyoctadecenoic, two are hydroxyheptadecenoic, and one is a hydroxy-octadecanoic acid, and two polyhydroxy acids — trihydroxystearic and dihydroxy-octadecinoic acids. The main acids in the combined material were 12-hydroxyoctadec-9-enoic acid and a trihydroxydecanoic acid.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 436–443, July–August, 1981. Original article submitted January 20, 1981.     

Determination of the content of hydroxy groups in cottonseed oil

IR spectroscopy has been used to determine the content of hydroxy groups in cottonseed oil in relation to the periods of ripening. It has been found that the largest amount of hydroxy groups is present in the oil of the early stages of ripeness.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 300–303, May–June, 1979.     

Epoxy and hydroxy acids of the seed oil ofGaleopsis bifida

The lipids of the seeds of the hemp nettle, which is toxic for ruminants have been studied. The composition of the fatty acids of five classes of lipids and the position-species composition of the triacylglycerols have been determined. The presence of epoxyacyl- and hydroxyacylglycerols in the oil and the structures of the acids of these lipids have been established. Squalene has been isolated from the oil.     

Extraction of cottonseed oil

Summary It has been shown that oil of the best quality is obtained on its selective extraction by hexane. Subsequent extraction from the meal of gossypol by 70–80% aqueous, and then dry, acetone permits meal to be obtained with a light cream color containing 0.02% of free gossypol. The omission of dry acetone leads to a darkening of the meal.It has been established that it is possible to achieve a reduction in the consumption of solvents on the direct extraction of cottonseed flake by using weak oil and gossypol miscellas.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 170–173, March–April, 1978.     

Epoxy and hydroxy acids of the seed oil ofGaleopsis bifida

The lipids of the seeds of the hemp nettle, which is toxic for ruminants have been studied. The composition of the fatty acids of five classes of lipids and the position-species composition of the triacylglycerols have been determined. The presence of epoxyacyl- and hydroxyacylglycerols in the oil and the structures of the acids of these lipids have been established. Squalene has been isolated from the oil.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 288–295, May–June, 1981.     

Triacylglycerols of fractionated cottonseed oil

The fatty-acid and triacylglycerol compositions of forepressing cottonseed oil and the refined and standard oils, and also of the palmitin fraction have been studied. It has been shown that the scheme of fractionation adopted does not give a clear separation of cottonseed oil into salad oil and palmitin. It has been found that typical compositions of the diunsaturated-monosaturated TAGs of the forepressing and refined and salad oils are practically the same, while the amount of diun-saturated-monosaturated TAGs in the palmitin fraction is far higher than in the others.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. SredazNIPKIPishcheprom [Central Asian Scientific-Research, Design, and Construction Institute of the Food Industry], Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 161–163, March–April, 1981.     

GC-MS analysis of hydroxy and epoxy acids from seed oil of Hippopha? rhamnoides

By the GC-MS method using a packed column, in the mixture of TMS derivatives of hydroxy acid methyl esters obtained from the seed oil of the sea buckthorn, in ten chromatographic peaks (CPs) 13 monohydroxy compounds have been characterized by their mass spectra, the main ones being derivatives of dimorphecolic and coriolic acids. Structures are proposed for four dihydroxy acids of the C₁₇–C₂₀ series. The mixture of methyl esters of di- and tetra-TMS derivatives obtained from the mixture of epoxy acids from the same source has been analyzed by a similar method. In seven CPs, 11 compounds, reflecting the presence of nine epoxy acids in the initial mixture, have been characterized by their mass spectra. The main component of the mixture was 15,16-epoxyoctadeca-9,12-dienoic acid.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 626–634, September–October, 1989.     

The question of the formation of isomeric fatty acids in the low-temperature hydrogenation of cottonseed oil in solvents

Conclusions 1. C-Glycosides have been isolated from a plant of the familyScrophulariaceae for the first time.2. Four new C-monoglycosides of apigenin have been isolated from the herbGratiola officinalis L.3. On the basis of a chemical study it has been established that they are rotation isomers and they have been characterized as a syn-C--D-glucopyranoside (avroside), an anti-C--D-glucopyranoside (isoavroside), a syn-C--D-glucopyranoside (neoavroside), and an anti-C--D-glucopyranoside (isoneoavroside).4. The presence of 6-C-monoglycosides in plants and their difference from 8-C-monoglycosides have been shown for the first time.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 19–24, 1970     

GC-MS analysis of hydroxy and epoxy acids from seed oil of Hippophaë rhamnoides

By the GC-MS method using a packed column, in the mixture of TMS derivatives of hydroxy acid methyl esters obtained from the seed oil of the sea buckthorn, in ten chromatographic peaks (CPs) 13 monohydroxy compounds have been characterized by their mass spectra, the main ones being derivatives of dimorphecolic and coriolic acids. Structures are proposed for four dihydroxy acids of the C₁₇–C₂₀ series. The mixture of methyl esters of di- and tetra-TMS derivatives obtained from the mixture of epoxy acids from the same source has been analyzed by a similar method. In seven CPs, 11 compounds, reflecting the presence of nine epoxy acids in the initial mixture, have been characterized by their mass spectra. The main component of the mixture was 15,16-epoxyoctadeca-9,12-dienoic acid.     

Substituted hydrazides of hydroxy carboxylic acids

The reaction of ethyl esters of arylhydrazides of oxalic acid with indolylmagnesium bromide has given arylhydrazides of N-indolylglyoxilic acid which, by reaction with benzoyl chloride, have been converted into -aryl--benzoylhydrazides of N-indolylglyoxilic acid. The reaction of arylmagnesium halides with arylhydrazides of indolylglyoxilic acid has given arylhydrazides of diarylglycolic acids. The spectra of the arylhydrazides of N-indolyglyoxilic acid have been studied.For Communication LXVI, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp. 1079–1082, August, 1970.     

Substituted hydrazides of hydroxy carboxylic acids

Under the action of concentrated sulfuric acid, a series of -alkyl--arylhydrazides of diarylglycolic acids is converted into 1-alkyl-1,2,3,4-tetrahydrocinnolin-3-ones. The reaction takes place through the intermediate formation of a halochromic salt.For Communication LXV, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 6, pp. 844–846, June, 1970.     

The fatty acid composition of the phospholipids of cottonseed oil

Summary 1. The phospholipids of cottonseed oil contain ten fatty acids.2. The positions of the double bonds in the aliphatic chain in the newly discovered unsaturated fatty acids — palmitlinoleic, palmitlinolenic, linolenic, and eicosadienic — have been established by the method of gas-liquid chromatography: they are present at the 6, 9; 6, 9, 12; 9, 12, 15; and 11, 14 carbon atoms, respectively, counting from the carboxyl end of the chain. A saturated fatty acid (myristic) has been found in the phospholipids of cottonseed oil for the first time.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 3, pp. 199–201, 1965     

Evaluation of polyblends of cottonseed protein and polycaprolactone plasticized by cottonseed oil

Recently, there has been an increasing trend toward replacing conventional fossil-based plastics with bioplastics that are eco-friendly and biodegradable. In this work, blends of polycaprolactone (PCL) and cottonseed protein plasticized with cottonseed oil were made and analyzed for their mechanical, adhesive, and thermal properties. The addition of water-washed cottonseed meal (WCSM) to PCL increased the Young’s modulus but decreased the tensile strength and elongation-at-break of PCL. The addition of cottonseed oil to the PCL/WCSM blend kept the tensile strength about the same but enhanced the elongation. The PCL blends with WCSM and cottonseed protein isolate gave about the same mechanical properties, both somewhat better than the PCL/soy protein isolate blend. As plasticizers, cottonseed oil performed slightly better than coconut oil, both better than poly(ethylene glycol). The addition of WCSM and cottonseed oil (up to a PCL:WCSM:plasticizer ratio of 60:40:20) did not change the adhesive performance of PCL on fiberboard. Thus, the combination of PCL/cottonseed protein/cottonseed oil seems to be a viable bioplastic, and one possible application for this material may be in the hot melt adhesive area.     

New hydroxy fatty acids of Acanthopanax sessiliflorus

The structures of six new hydroxy fatty acids from the hydroxyacyldiacylglycerols of the fruit ofAcanthopanax sessiliflorus (Rupr. et amaxim.) Seem. (family Araliaceae have been established as 6-hydroxyhexadeca-12Z-enoic, 6-hydroxyhexadeca-9Z,12Z-dienoic, and the isomeric 6- and 7-hydroxyoctadeca-12-Z-enoic, and 6- and 7-hydroxyoctadeca-9Z,12Z-dienoic acids and their quantitative amounts have been determined with the aid of spectral, chromatographic, and chemical methods of analysis. Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 616–619, September–October, 1991.     

New hydroxy fatty acids of Acanthopanax sessiliflorus

The structures of six new hydroxy fatty acids from the hydroxyacyldiacylglycerols of the fruit ofAcanthopanax sessiliflorus (Rupr. et amaxim.) Seem. (family Araliaceae have been established as 6-hydroxyhexadeca-12Z-enoic, 6-hydroxyhexadeca-9Z,12Z-dienoic, and the isomeric 6- and 7-hydroxyoctadeca-12-Z-enoic, and 6- and 7-hydroxyoctadeca-9Z,12Z-dienoic acids and their quantitative amounts have been determined with the aid of spectral, chromatographic, and chemical methods of analysis.Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 616–619, September–October, 1991.     

Stereospecific analysis of the triacylglycerols of cottonseed oil

A stereospecific analysis has been made of the triacylglycerols of cottonseed oil, as a result of which it has been established that the saturated and 16:1 acids mainly occupy the sn-1 position, while 18:1 and 18:2 acids esterify the sn-2 and sn-3 positions of the triacylglycerides to equal extents.     

Dicarboxylic acids and hydroxy fatty acids in different species of fungi

Secondary metabolites of fungi can be responsible for allergies; therefore, the identification of compounds produced by these organisms is very important. Fungi produce large amounts of secondary metabolites, which belong to groups of chemicals such as: dicarboxylic acids, hydroxy acids, alcohols, hydrocarbons, esters, fatty acids, sterols, amino acids and mycotoxins. The presence of all these compounds in human proximity contributes to many diseases. Therefore, the aim of the study was a qualitative and quantitative analysis of hydroxy and dicarboxylic acids produced by fungi occurring in student hostel in Poland, in the province of Pomerania. The following species of fungi were subjected to extraction: Aspergillus niger, Aspergillus fumigatus, Aspergillus candidus, Rhizopus sp., Geotrichum candidum, and Penicillium chrysogenum. A mixture of ethyl acetate and methanol was used for the extraction. The obtained extracts were further analyzed by gas chromatography mass spectrometry (GC–MS). In all samples of fungi, the presence of a total of 22 acids, including 13 dicarboxylic and 9 hydroxy acids, was confirmed. Most acids (17 different acids) were identified in A. fumigatus. Only 10 acids were identified in the mycelium of G. candidum and A. niger. Acids which were identified in all samples of the mycelium were 22-hydroxydocosanoic acid, 24-hydroxytetracosanoic acid and adipic acid. The most abundant compounds were 22-hydroxydocosanoic acid in A. fumigatus, A. candidus, Rhizopus sp., G. candidum and P. chrysogenum, and succinic acid in A. niger. More experiments are needed to understand the physiological role of hydroxy and dicarboxylic acids. We hope that our results are an important contribution to further studies on the human health.