Quantitative analysis of synthetic mixtures of triacylglycerols with fatty acids from caprylic to stearic

Fabien, Robert J.; Craske, John D.; Wootton, M.

doi:10.1007/bf02545317

Cited by 10 publications

(2 citation statements)

References 13 publications

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“…Trilaurin has been analyzed/identi ed using the following methods: infrared (IR) spectroscopy (Deman and Deman 1982); mass spectroscopy (STN International 1997b); nuclear magnetic resonance (NMR) spectroscopy (STN International 1997c); capillary supercritical uid chromatography (Giron, Link, and Bouissel 1992); nonaqueous reverse phase, high-performanc e liquid chromatography (Fabien, Craske, and Wootton 1993); and high-performance size-exclusion chromatography (Lubke, Le Quere, and Barron 1996).…”

Section: Methodsmentioning

confidence: 99%

Final Report on the Safety Assessment of Trilaurin, Triarachidin, Tribehenin, Tricaprin, Tricaprylin, Trierucin, Triheptanoin, Triheptylundecanoin, Triisononanoin, Triisopalmitin, Triisostearin, Trilinolein, Trimyristin, Trioctanoin, Triolein, Tripalmitin, Tripalmitolein, Triricinolein, Tristearin, Triundecanoin, Glyceryl Triacetyl Hydroxystearate, Glyceryl Triacetyl Ricinoleate, and Glyceryl Stearate Diacetate

2001

Int J Toxicol

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Triesters of glycerin and aliphatic acids, known generically as glyceryl triesters and specifically as Trilaurin, etc., are used in cosmetic products as occlusive skin-conditioning agents and/or non-aqueous viscosity-increasing agents. Hundreds of glyceryl triesters are used in a wide variety of cosmetic products at concentrations ranging from a few tenths of a percent to 46%. Glyceryl triesters are also known as triglycerides; ingested triglycerides are metabolized to monoglycerides, free fatty acids, and glycerol, all of which are absorbed in the intestinal mucosa and undergo further metabolism. Dermal absorption of Triolein in mice was nil; the oil remained at the application site. Only slight absorption was seen in guinea pig skin. Tricaprylin and other glyceryl triesters have been shown to increase the skin penetration of drugs. Little or no acute, subchronic, or chronic oral toxicity was seen in animal studies unless levels approached a significant percentage of caloric intake. Subcutaneous injections of Tricaprylin in rats over a period of 5 weeks caused a granulomatous reaction characterized by oil deposits surrounded by macrophages. Dermal application was not associated with significant irritation in rabbit skin. Ocular exposures were, at most, mildly irritating to rabbit eyes. No evidence of sensitization or photosensitization was seen in a guinea pig maximization test. Most of the genotoxicity test systems were negative. Tricaprylin, Trioctanoin, and Triolein have historically been used as vehicles in carcinogenicity testing of other chemicals. In one study, subcutaneous injection of Tricaprylin in newborn mice produced more tumors in lymphoid tissue than were seen in untreated animals, whereas neither subcutaneous or intraperitoneal injection in 4-to 6-week-old female mice produced any tumors in another study. Trioctanoin injected subcutaneously in hamsters produced no tumors. Trioctanoin injected intraperitoneally in pregnant rats was associated with an increase in mammary tumors in the offspring compared to that seen in offspring of untreated animals, but similar studies in pregnant hamsters and rabbits showed no tumors in the offspring. One study of Triolein injected subcutaneously in rats showed no tumors at the injection site. As part of an effort to evaluate vehicles used in carcinogenicity studies, the National Toxicology Program conducted a 2-year carcinogenicity study in rats given Tricaprylin by gavage. This treatment was associated with a statistically significant dose-related increase in pancreatic acinar cell hyperplasia and adenoma, but there were no acinar carcinomas, the incidence of mononuclear leukemia was less, and nephropathy findings were reduced, all compared to corn oil controls. Overall, the study concluded that Tricaprylin did not offer significant advantages over corn oil as vehicles in carcinogenicity studies. Trilaurin was found to inhibit the formation of neoplasms initiated by dimethylbenzanthracene (DMBA) and promoted by croton oil. Tricaprylin was not teratogenic in mice or rats, but some reproductive effects were seen in rabbits. A low level of fetal eye abnormalities and a small percentage of abnormal sperm were reported in mice injected with Trioctanoin as a vehicle control. Clinical tests of Trilaurin at 36.3% in a commercial product applied to the skin produced no irritation reactions. Trilaurin, Tristearin, and Tribehenin at 40%, 1.68%, and 0.38%, respectively, in commercial products were also negative in repeated-insult patch tests. Tristearin at 0.32% in a commercial product induced transient, mild to moderate, ocular irritation after instillation into the eyes of human subjects. Based on the enhancement of penetration of other chemicals by skin treatment with glyceryl triesters, it is recommended that care be exercised in using them in cosmetic products. On the basis of the available data, the following 23 glyceryl triesters are considered safe as used in cosmetics: Trilaurin, Triarachidin, Tribehenin, Tricaprin, Tricaprylin, Trierucin, Triheptanoin, Triheptylundecanoin, Triisononanoin, Triisopalmitin, Triisostearin, Trilinolein, Trimyristin, Trioctanoin, Triolein, Tripalmitin, Tripalmitolein, Triricinolein, Tristearin, Triundecanoin, Glyceryl Triacetyl Hydroxystearate, Glyceryl Triacetyl Ricinoleate, and Glyceryl Stearate Diacetate. Some of these are not currently in use, but would be considered safe if used at concentrations similar to those glyceryl triesters that are in use as cosmetic ingredients.

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Section: Methodsmentioning

confidence: 99%

Final Report on the Safety Assessment of Trilaurin, Triarachidin, Tribehenin, Tricaprin, Tricaprylin, Trierucin, Triheptanoin, Triheptylundecanoin, Triisononanoin, Triisopalmitin, Triisostearin, Trilinolein, Trimyristin, Trioctanoin, Triolein, Tripalmitin, Tripalmitolein, Triricinolein, Tristearin, Triundecanoin, Glyceryl Triacetyl Hydroxystearate, Glyceryl Triacetyl Ricinoleate, and Glyceryl Stearate Diacetate

2001

Int J Toxicol

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“…The ECN value is employed to reaffirm the order of HPLC elution of various triacylglycerol molecular species [24]. As exact chromatographic peak assignment is not possible merely based on ECN values of triacylglycerols, the detailed chromatographic peak identification is achieved by the approach of logarithms of retention volumes [18,25].…”

Section: Identification Of Chromatographic Peaksmentioning

confidence: 99%

Enzymatic synthesis of structured lipids with behenic acid at the sn-1, 3 positions of triacylglycerols

Kok

Chuah

Cheng

2017

Food Sci Biotechnol

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A long chain saturated fatty acid (SFA), behenic acid, is incorporated into the -1, 3 positions of triacylglycerols in palm olein (POo) and high-oleic sunflower oil (HOS) by solvent-free interesterification catalyzed by Lipozyme RM IM. The enzymatic interesterified HOS (EIE-HOS) yielded 76.5% of BOO and BOB as compared to 45.6% in POo (EIE-POo). The-2 position of EIE-HOS displayed 5.3 mol% of SFA which is significantly lower compared to 13.5 mol% in EIE-POo ( < 0.001). The -1, 3 positions of EIE-POo exhibited greater amount of behenic acid (82.0 mol%) in relation to EIE-HOS (64.0 mol%) ( < 0.001). Due to the greater variety of constitutive triacylglycerol, EIE-POo showed greater differences between onset (To) and offset temperature (Tf) in the melting endotherms (76.99 °C) as compared to EIE-HOS (68.65 °C), and may offer more intensive cooling sensation and flavor release.

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Lipid Analyses in Food

Marini¹

2000

Encyclopedia of Analytical Chemistry

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The term lipid encompasses a great host of compounds (e.g. fatty acids (FAs), mono‐, di‐ and triglycerides), that are almost ubiquitously present in foods; their characterization and quantification is then of importance for an analytical chemist. The first step for an accurate analysis is sample preparation: choosing an appropriate solvent or phases can isolate one particular class of lipid from a sample [a good separation of classes can be accomplised by thin‐layer chromatography (TLC)]; obviously, the sample pretreatment will be governed by the determinations to follow. Indeed, nowadays, there is a host of techniques, mainly chromatographic, for lipid analysis. TLC is a rapid way to gather information about the sample (presence of conjugated double and triple bonds, free FAs and of oxygenated FAs), particularly with the development of modified normal phases. For example, silica gel can be impregnated with boric acid, which inhibits isomerization of mono‐ and diglycerides, or it can be treated with silver ions [argentation, for silver ion thin‐layer chromatography (Ag‐TLC)] used for resolution of unsaturated FAs. Gas chromatography (GC) and high‐performance liquid chromatography (HPLC) are the most common techniques actually employed, because of their versatility (many parameters can be changed, e.g. stationary and mobile phases, detector) and to their capacity to be hyphenated (coupled with another measuring device). Particularly, the advent of the light‐scattering detector has allowed greater reproducibility in the HPLC of lipids. Mass spectrometry (MS) is often coupled with GC. However, coupling MS with another MS (MS/MS or tandem MS) is useful for the determination of the structure of long‐chain FAs with improved selectivity and sensitivity. Finally, nuclear magnetic resonance (NMR) is able to identify functional groups, even in mixtures, and is a valid aid for the elucidation of structures with double bonds (DBs) by interpretation of the coupling patterns. Each analytical method relies on appropriate sample preparation (e.g. methylation for the GC analysis of FAs) and a critical approach to evaluate its usefulness.

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Quantitative analysis of synthetic mixtures of triacylglycerols with fatty acids from caprylic to stearic

Cited by 10 publications

References 13 publications

Enzymatic synthesis of structured lipids with behenic acid at the sn-1, 3 positions of triacylglycerols

Lipid Analyses in Food

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