Skin Penetration Enhancing Action of cis-Unsaturated Fatty Acids with .OMEGA.-9, and .OMEGA.-12-Chain Lengths.

Takeuchi, Yoshikazu; Yamaoka, Yumiko; Fukushima, Shoji; Miyawaki, Kohji; Taguchi, Kenji; Yasukawa, Hidehito; Kishimoto, Syuichi; Suzuki, Masao

doi:10.1248/bpb.21.484

Cited by 30 publications

(15 citation statements)

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“…Fatty acids can have a variety of chain lengths, double bonds characteristics (position, number, and configuration), branching schema, and substituents. These structural variations can affect their suitability as skin penetration enhancers (18)(19)(20)(21). Fatty acids can insert between the hydrophobic tails of the stratum corneum lipid bilayer, disturbing their packing, increasing their fluidity, and subsequently, decreasing the diffusional resistance to permeants (22).…”

Section: Resultsmentioning

confidence: 99%

Enhanced transdermal delivery of loratadine from the EVA matrix

2009

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Section: Resultsmentioning

confidence: 99%

Enhanced transdermal delivery of loratadine from the EVA matrix

2009

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“…Some of the genera are known for their high level of petroselinic (cis-6 18:1) acid in seed oils, which represent an interesting oleochemical for the food, cosmetics, and pharmaceutical industries [3][4][5]. For example, petroselinic acid can be cleaved into lauric (12:0) acid and adipic (hexanedioic) acid, providing environmentally friendly sources of these valuable acids as they are derived from renewable oil seed crops [6,7].…”

Section: Introductionmentioning

confidence: 99%

Triacylglycerols of Apiaceae seed oils: Composition and regiodistribution of fatty acids

Ngo‐Duy

Destaillats

Keskitalo

et al. 2009

Euro J Lipid Sci & Tech

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Oils from the seeds of caraway (Carum carvi), carrot (Daucus carota), celery (Apium graveolens) and parsley (Petroselinum crispum), all from the Apiaceae family, were analyzed by gas chromatography for their triacylglycerol (TAG) composition and fatty acid (FA) distribution between the sn-1(3) and sn-2 positions of TAG. Twenty-two TAG species were quantified. Glyceryl tripetroselinate was the major TAG species in seed oils of carrot, celery and parsley, with levels ranging from 38.7 to 55.3%. In caraway seed oil, dipetroselinoyllinoleoylglycerol was the major TAG species at 21.2%, while the glyceryl tripetroselinate content was 11.4%. Other TAG species were linoleoyloleoylpetroselinoylglycerol and dipetroselinoyloleoylglycerol. Predominantly, TAG were triunsaturated (72.2-84.0%) with diunsaturates at 14.4-25.9%, and small amounts of monounsaturated TAG. Results for regiospecific analysis showed a non-random FA distribution in Apiaceae for palmitic, petroselinic, linoleic and oleic acids. Petroselinic acid was predominantly located at the sn-1(3) position in carrot, celery and parsley seed oils, while it was mainly at the sn-2 position in caraway seed oil. The distribution of linoleic acid was opposite to that of petroselinic acid. Oleic acid was mostly located at the sn-2 position, except for caraway, where it was evenly distributed between the sn-1(3) and sn-2 positions. Both the saturated FA, palmitic and stearic acid, were located mainly at the sn-1(3) position. The presence of a high level of tripetroselinin in parsley seed oil (55.3%) makes it a potential source for the production of petroselinic acid.

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“…Fatty acids are known to enter the hydrophobic tails of the stratum corneum lipid bilayer, disturbing their packing, increasing their fluidity, and subsequently, decreasing the diffusional resistance to permeates (Golden et al 1987). The effect of varying carbon-chain lengths, degrees and types of unsaturation (position, number), the branching schema, and substituents has been reported to influence the ability of fatty acids to act as skin penetration enhancers (Elyan et al 1996;Bhatia and Singh 1998;Takeuchi et al 1998;Taguchi et al 1999). In this study, the effects of 12 fatty acids on the transdermal delivery of diclofenac in vitro have been systematically investigated.…”

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confidence: 99%