Structure of Sterculic Acid

Verma, Jason; Nath, Bhola; Aggarwal, J. S.

doi:10.1038/175084a0

Cited by 25 publications

(7 citation statements)

References 4 publications

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“…The spectra of sterculic acid and some of its derivatives were exanlined to obtain evidence for the structure of the acid, which has been in dispute (4,5)." *Shortly after our work was completed, the proton resonance spectrum of sterculic acid was reported by Rinelmrt, ~Vilssott, and Whaley (6).…”

Section: Consbitution Of Sterculic Acidmentioning

confidence: 97%

Applications of Proton Magnetic Resonance Spectra in Fatty Acid Chemistry

Hopkins¹,

Bernstein²

1959

Can. J. Chem.

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An introductory study has been made of the proton magnetic resonance spectra of fatty acids, fatty acid esters, and natural glyceride oils. Characteristic signals were recorded for the hydrogens of such groupings as hydroxy, acetoxy, and epoxy; isolated, conjugated, and methylene-interrupted double bonds; and others. Examples are given of the application of this technique in identifying the fatty acids of natural glyceride oils. Semiquantitative estimations are shown to be feasible. Evidence for Nunn's formula for sterculic acid is discussed on the basis of the spectra of the acid and its derivatives.Proton magnetic resonance measurements provide a new method of distinguishing certain groupings in fatty acid molecules. This preliminary study indicates that the method is of value in determining the structure of fatty acids and their derivatives and in estimating in a roughly quantitative manner the proportions of certain fatty acids in mixtures. Quantitative estimation is applicable in some degree to single mixed glycerides and to natural oils, which are mainly mixtures of mixed glycerides.Small amounts of impurities are not likely to interfere, since componeilts constituting less than 5% of the sample do not usually give a measurable signal.In the present work measurements were made with a Varian V-4300 NMR spectrometer operating a t a frequency of 40 Mc/s and equipped with a Varian Field Stabilizer. Each sample was dissolved in chloroform a t sufficiently high concentration to give signals of moderate intensity. Some of the oxygenated acids were used a t maximum solubility. Usually 0.2 to 0.5 g of sample was dissolved in 0.5 to 1.0 ml of chloroform. T h e sample tube was 5 mm 0.d. and was set spinning by a jet of nitrogen.Chemical shifts were measured from the dissolved chloroform signal or that of the long-chain CH2 signal by the well-known side-band technique. All chemical shifts were referred to the long-chain CH2 signal, the signals a t lower applied field having negative values. All figures are displayed with applied magnetic field increasing toward the right. MATERIALSOleic acid, methyl oleate, and methyl linoleate were prepared from natural oils by fractional distillation of the esters followed by low-temperature crystallization. 9,lODiacetoxystearic acid was made by acetylating the pure dihydroxy acid. 12,13-Dihydroxyoleic acid was prepared from the seed oil of Vernonia colorata by Gunstone's procedure (I). Commercial ethyl ricinoleate was purified by low-temperature crystallization.Vernonia oil and Stercz~lia oil were extracted in the laboratory from seed of Vernonia colorata and Sterculia foetida respectively. T h e other oils and the lauric acid were commercial products. Methyl 10,12-octadecadienoate was kindly supplied by Dr. 0. S. Privett.Sterculic acid was made by cold saponification of Sterculia oil, followed by repeated crystallization from acetone a t low temperature. I t was hydrogenated with palladium 'Manuscript

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Section: Consbitution Of Sterculic Acidmentioning

confidence: 97%

Applications of Proton Magnetic Resonance Spectra in Fatty Acid Chemistry

Hopkins¹,

Bernstein²

1959

Can. J. Chem.

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“…For example, oil-producing microbes can be considered as appropriate vehicles in which foreign (plant) genes could be cloned for the production of commercially attractive fatty acids such as nervonic acid (C24:1 Δ15) obtained from Honesty ( Lunaria ), 3 which is used in small amounts in the treatment of particular neuropathies. Another example is sterculic acid {ω-(2 n -octylcycloprop-1-enyl)-octanoic acid}, 168 which has been considered as a treatment for certain cancers of the bowel. One more promising example is represented by the non-methylene-interrupted fatty acids (e.g., C20:3 Δ5, Δ11, Δ14), which can be obtained from Juniperus chinensis seed oil and is known to reduce the amount of arachidonic acid in certain phospholipid pools and, thus, act to alter eicosanoid signaling.…”

Section: Future Perspectivesmentioning

confidence: 99%

Accumulation of High-Value Lipids in Single-Cell Microorganisms: A Mechanistic Approach and Future Perspectives

Garay

Boundy‐Mills

German

2014

J. Agric. Food Chem.

134

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In recent years attention has been focused on the utilization of microorganisms as alternatives for industrial and nutritional applications. Considerable research has been devoted to techniques for growth, extraction, and purification of high-value lipids for their use as biofuels and biosurfactants as well as high-value metabolites for nutrition and health. These successes argue that the elucidation of the mechanisms underlying the microbial biosynthesis of such molecules, which are far from being completely understood, now will yield spectacular opportunities for industrial scale biomolecular production. There are important additional questions to be solved to optimize the processing strategies to take advantage of the assets of microbial lipids. The present review describes the current state of knowledge regarding lipid biosynthesis, accumulation, and transport mechanisms present in single-cell organisms, specifically yeasts, microalgae, bacteria, and archaea. Similarities and differences in biochemical pathways and strategies of different microorganisms provide a diverse toolset to the expansion of biotechnologies for lipid production. This paper is intended to inspire a generation of lipid scientists to insights that will drive the biotechnologies of microbial production as uniquely enabling players of lipid biotherapeutics, biofuels, biomaterials, and other opportunity areas into the 21st century.

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“…The structure of w-(2-n-octylcycloprop-l-enyl)octanoic acid (LVIII) was assigned to sterculic acid on the basis of the reactions (196) shown in Scheme II. Varma and his co-workers (262,264,265) rejected this structure and instead proposed the structure «-(2-nhexylcyclopropyl)dec-9-enoic acid (LIX) on the basis of an incorrect interpretation of infrared data, the supposed synthesis of the methyl ester of the acid of structure LVIII, and the isolation of certain compounds from the oxidation of the isolated acid. Their propane ring and to the double bond in the chain (264).…”

Section: Proof Of Structurementioning

confidence: 99%