Safety Assessment of Triethanolamine and Triethanolamine-Containing Ingredients as Used in Cosmetics

Fiume, Monice M.; Heldreth, Bart; Bergfeld, Wilma F.; Belsito, D.; Hill, Ronald A.; Klaassen, Curtis D.; Liebler, D.C.; Marks, James G.; Shank, Ronald C.; Slaga, Thomas J.; Snyder, Paul W.; Andersen, F. Alan

doi:10.1177/1091581813488804

Cited by 43 publications

(23 citation statements)

References 55 publications

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“…[20] Compound 6b is obtained as am ixture of diastereoisomers, as can be seen from the NMR spectra:a lthought heir chemical shifts are close, the 13 CNMR spectra clearly show 3d istinct resonances for the RRR, RSS and RSR diastereomers (and their respective antipodes). The related tris(2-hydroxylalkyl)amines derived from ethylenea nd propylene oxide, [1a] have found extensive use (for example:m ain group atranes, [21] tripodall igands in coordination chemistry [22] and catalysis, [23] cosmetics additives [24] ). On the other hand, the corresponding 3-hydroxyalkyl aminesh ave not been extensively investigated.…”

Section: Resultsmentioning

confidence: 99%

Oxa‐Michael Addition to α,β‐Unsaturated Nitriles: An Expedient Route to γ‐Amino Alcohols and Derivatives

et al. 2018

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Water addition to α,β‐unsaturated nitriles would give facile access to the β‐hydroxy‐nitriles, which in turn can be hydrogenated to the γ‐amino alcohols. We have previously shown that alcohols readily add in 1,4‐fashion to these substrates using Milstein's Ru(PNN) pincer complex as catalyst. However, attempted water addition to α,β‐unsaturated nitriles gave the 3‐hydroxynitriles in mediocre yields. On the other hand, addition of benzyl alcohol proceeded in excellent yields for a variety of β‐substituted unsaturated nitriles. Subsequent treatment of the benzyl alcohol addition products with TMSCl/FeCl3 resulted in the formation of 3‐hydroxy‐alkylnitriles. The 3‐benzyloxy‐alkylnitriles obtained from oxa‐Michael addition also could be hydrogenated directly in the presence of acid to give the amino alcohols as their HCl salts in excellent yields. Hydrogenation under neutral conditions gave a mixture of the secondary and tertiary amines. Hydrogenation in the presence of base and Boc‐anhydride gave the orthogonally bis‐protected amino alcohols, in which the benzyl ether can subsequently be cleaved to yield Boc‐protected amino alcohols. Thus, a variety of molecular scaffolds with a 1,3‐relationship between O‐ and N‐functional group is accessible starting from oxa‐Michael addition of benzyl alcohol to α,β‐unsaturated nitriles.

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Section: Resultsmentioning

confidence: 99%

Oxa‐Michael Addition to α,β‐Unsaturated Nitriles: An Expedient Route to γ‐Amino Alcohols and Derivatives

et al. 2018

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“…Hand creams containing triethanolamine, an emulsifier and thickener, yielded similar in vivo CHG inactivation [8] . Based on the Cosmetic Ingredient Review (CIR) Expert Panel, triethanolamine, carbomer, and C10-C30 alkyl acrylate crosspolymer were found in 3756, 1610 and 1696 cosmetic formulations, respectively [28][29][30] . This demonstrated the prevalence of these compounds as well as the potential for inactivation if concurrently applied.…”

Section: Discussionmentioning

confidence: 99%

Evidence of incompatibility for topical anionic agents used in conjunc-tion with chlorhexidine gluconate: A systematic review

Tran¹,

Huynh²,

Bruins³

et al. 2016

J Surg Dermatol

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<p>Chlorhexidine gluconate (CHG) is a widely used antiseptic agent for skin and wound disinfection. The cationic properties of CHG may allow its inactivation and precipitation by anionic agents in commonly used topical agents. We conducted a systematic review by searching through PubMed, Cochrane Library, and Web of Science databases and selected original research articles reporting on CHG incompatibility, defined as inactivation or precipitation. The search yielded 22 publications that demonstrated CHG incompatibility via: 1) reduced antibacterial activity (carbomer, acrylates/C10-C30 alkyl acrylate crosspolymer, dentin, bovine serum albumin, copolymer M239144, sodium lauryl sulfate, heat-killed microbes, triethanolamine, and bark cork); and 2) visible precipitate formation (sodium hypochlorite, EDTA, saline, ethanol, andnystatin). Only three publications reported on CHG incompatibility in dermatology, specifically for carbomer, triethanolamine, and acrylates/C10-C30 alkyl acrylate crosspolymer. Although limited evidence linking CHG incompatibility and anionic agents exists, clinicians should carefully consider the nature of topical agents used if CHG is concurrently applied. Increased awareness of CHG incompatibility may result in better antibacterial activity thus ensuring optimal patient management.</p>

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“…The degradation products or byproducts 12 For ions (1)-(5) see Scheme 2, for ion (6) see Scheme S5 (supporting information), for ions (7) and (8) see Scheme S6 (supporting information), for ion (9) see Scheme S7 (supporting information).…”

Section: Selection Of Perfluoroacylation Over Silylationmentioning

confidence: 99%

“…The spectra of the perfluoroacyl derivatives of the halfNMs are similar to those of the corresponding EAs. [14][15][16] The EI mass spectra of all the derivatives of the halfNMs are shown in Figure 3 For ions (1)-(5) see Scheme 2, for ion (6) see Scheme S5 (supporting information), for ions (7) and (8) see Scheme S6 (supporting information), for ion (9) see Scheme S7 (supporting information).…”

Section: Ei-ms Interpretationmentioning

confidence: 99%

“…8 In addition, EAs can be used in the production of cosmetics. 9,10 Thus, these industries are subject to the CWC verification program conducted by the Organisation for the Prohibition of Chemical Weapons (OPCW). 2 During any OPCW inspection, non-compliance cannot be based on the identification of EAs, but the presence of partially hydrolyzed products of NMs, i.e.…”

Section: Introductionmentioning

confidence: 99%

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Mass spectral fragmentation of perfluoroacyl derivatives of half nitrogen mustards for their detection by gas chromatography/mass spectrometry

Chandra

Roy

Shaik

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale:Analytical methods for the detection and identification of half nitrogen mustards (halfNMs), i.e., partially hydrolyzed products of nitrogen mustards (pHpNMs), using silyl derivatives are often associated with low sensitivity and selectivity. In order to overcome these limitations, the derivatization of halfNMs was performed using perfluoroacylation.Methods: Two efficient derivatization techniques using trifluoroacetyl (TFA) and heptafluorobutyryl (HFB) groups were developed for the unambiguous identification of halfNMs. A mass spectral database was generated by performing gas chromatography/electron ionization mass spectrometry (GC/EI-MS) and gas chromatography/positive chemical ionization mass spectrometry (GC/PCI-MS). The fragmentation pathways were studied by tandem mass spectrometry (MS/MS) in both EI and PCI mode. Results:The EI-MS spectra of the TFA and HFB derivatives of halfNMs contain intense molecular ions and fragment ions, thus making perfluoroacylation preferable to silylation. In addition, the background-free chromatogram obtained using these derivatives provides unambiguous identification of these compounds in blind samples. The structures of the fragment ions were postulated, and the sources of significant ions were traced by performing MS/MS precursor ion scans. In the PCI-MS spectra, along with the protonated molecule, significant peaks due to neutral losses of HF, HCl, CH 3 Cl and CF 3 COOH were observed.Conclusions: This is the first report of the elucidation of the fragmentation pathways of perfluoroacyl derivatives of halfNMs. The complementary GC/PCI-MS and GC/PCI-MS/MS data will be helpful in the identification of unknown metabolites in a fast and reliable fashion.

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Safety Assessment of Triethanolamine and Triethanolamine-Containing Ingredients as Used in Cosmetics

Cited by 43 publications

References 55 publications

Oxa‐Michael Addition to α,β‐Unsaturated Nitriles: An Expedient Route to γ‐Amino Alcohols and Derivatives

Oxa‐Michael Addition to α,β‐Unsaturated Nitriles: An Expedient Route to γ‐Amino Alcohols and Derivatives

Evidence of incompatibility for topical anionic agents used in conjunc-tion with chlorhexidine gluconate: A systematic review

Mass spectral fragmentation of perfluoroacyl derivatives of half nitrogen mustards for their detection by gas chromatography/mass spectrometry

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