The Acidic Constituents of Degras. A New Method of Structure Elucidation<sup>1</sup>

Weitkamp, A. W.

doi:10.1021/ja01219a027

Cited by 163 publications

(51 citation statements)

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“…These starter units are elongated by fatty acid synthases to the final iso-fatty acids (even numbered for isobutyryl-CoA; odd-numbered for isovaleryl-CoA) through extension with malonyl-CoA [21–22]. Long-chain iso-fatty acids are important analytical reference compounds owing to the presence of these materials in tobacco [23], wool wax [24], butter fat [25], human sebaceous secretions [26] (adult skin [27], meibum [28], cerumen [29], and newborn vernix caseosa [30–31]), and a wide variety of microbiological samples [1]. …”

Section: Introductionmentioning

confidence: 99%

A practical synthesis of long-chain iso-fatty acids (iso-C₁₂–C₁₉) and related natural products

Richardson¹,

Williams²

2013

Beilstein J. Org. Chem.

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SummaryA gram-scale synthesis of terminally-branched iso-fatty acids (iso-C12–C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12–C14) or the C15 and C16 lactones pentadecanolide (for iso-C15–C17) and hexadecanolide (for iso-C18–C19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/lactones and selective reduction of the resulting tertiary alcohols. Thus, the C12, C17 and C18 iso-fatty acids were obtained in three steps from commercially-available starting materials, and the remaining C13–C16 and C19 iso-fatty acids were prepared by homologation or recursive dehomologations of these fatty acids or through intercepting appropriate intermediates. Highlighting the synthetic potential of the iso-fatty acids and various intermediates prepared herein, we describe the synthesis of the natural products (S)-2,15-dimethylpalmitic acid, (S)-2-hydroxy-15-methylpalmitic acid, and 2-oxo-14-methylpentadecane.

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Section: Introductionmentioning

confidence: 99%

A practical synthesis of long-chain iso-fatty acids (iso-C₁₂–C₁₉) and related natural products

Richardson¹,

Williams²

2013

Beilstein J. Org. Chem.

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“…Tuberculostearic acid and its homologs, which have a methyl group substituted in the hydrocarbon chain, are found in Tubercule bacilli (6,7) and Microbispora cbromogenes M-22 (8). lso acids and anteiso fatty acids, which are substituted, respectively, on the next to last carbon and at the second from the last carbon, are obtained from a number of natural sources (9)(10)(11)(12)(13). Methylation of cellular lipid from the methyl group of methionine has been investigated in Agrobacterium turnefaciens (14), in Corynebacterium simplex grown on n-alkanes (15) and n-alkenes (16), and in Mycobacterium pblei (17).…”

Section: Introductionmentioning

confidence: 99%

Production of branched‐chain fatty acids from sterculia oil

Kai

Pryde

1982

J Americ Oil Chem Soc

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Methyl sterculate was rearranged by use of 0.5% of rhodium catalyst to isomeric conjugated diene fatty acid methyl esters containing both methylene-and methyl-branched isomers. The rearranged products were hydrogenated directly to saturated, methyl-substituted, branched-chain fatty acid methyl esters with the methyl substituent at one of the positions formerly occupied by the cyclopropenoid ring. The crude branched-chain fatty acids from these esters were purified by recrystallization from a mixed solvent of ethanol and water (80:20, v/v) and flash distillation; the producf contained about 90% of branched-chain fatty acids (Ct9:80%, C18:10%). Esters of the branched-chain fatty acid were prepared with 2-ethylhexyl alcohol or trimethylolpropane, and the characteristic properties of these esters were investigated. The branchedchain fatty esters appear to have potential utility in lubricants; other uses may be possible.

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“…Downing and Lindholm (1982) indicated that the majority of aliphatic components in cattle sebum are above C12, however, a C10 fatty acid component was reported. Both capric acid (0.3%) and stearic acid (0.2%) are present in wool wax of sheep (Weitkamp 1945), but it is not known if they are in cattle sebum.…”

Section: Skin Secretionsmentioning

confidence: 99%

Topically applied myco-acaricides for the control of cattle ticks: overcoming the challenges

Polar¹,

Moore

Kairo

et al. 2008

Exp Appl Acarol

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In the absence of commercially viable and environmentally friendly options, the management of cattle ticks is heavily dependent on the use of chemical acaricides. Due to recent advances in production, formulation and application technology, commercial fungus-based biological pesticides (myco-insecticides, myco-acaricides) are becoming increasingly popular for the control of plant pests; however, they have not been used against animal ectoparasites. The literature clearly demonstrates that entomopathogenic fungi are pathogenic to ticks under laboratory conditions. Pasture applications have also shown promise while experiments on topical application have had variable results. These results suggest that major research hurdles still exist especially for the latter. Although literature on ticks and their interactions with entomopathogenic fungi exists, there is not a clear understanding on how this can be influenced by the microenvironment of the cattle skin surface. This paper critically reviews pathogen, tick target and host skin microenvironmental factors that potentially affect pathogenicity of the applied entomopathogen. Factors influencing the route of infection for topically applied myco-acaricides are also reviewed. Major researchable constraints and recommendations are identified and prioritized. In particular, there is the need for basic studies to understand the interaction of entomopathogenic fungi with the components of the skin microenvironment, to identify suitable strains, and to develop improved formulations to overcome the various challenges.

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The Acidic Constituents of Degras. A New Method of Structure Elucidation¹

Cited by 163 publications

References 0 publications

A practical synthesis of long-chain iso-fatty acids (iso-C₁₂–C₁₉) and related natural products

A practical synthesis of long-chain iso-fatty acids (iso-C₁₂–C₁₉) and related natural products

Production of branched‐chain fatty acids from sterculia oil

Topically applied myco-acaricides for the control of cattle ticks: overcoming the challenges

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The Acidic Constituents of Degras. A New Method of Structure Elucidation1

Cited by 163 publications

References 0 publications

A practical synthesis of long-chain iso-fatty acids (iso-C12–C19) and related natural products

A practical synthesis of long-chain iso-fatty acids (iso-C12–C19) and related natural products

Production of branched‐chain fatty acids from sterculia oil

Topically applied myco-acaricides for the control of cattle ticks: overcoming the challenges

Contact Info

Product

Resources

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The Acidic Constituents of Degras. A New Method of Structure Elucidation¹

A practical synthesis of long-chain iso-fatty acids (iso-C₁₂–C₁₉) and related natural products

A practical synthesis of long-chain iso-fatty acids (iso-C₁₂–C₁₉) and related natural products