2-bromo-2-nitropropane-1,3-diol as a nitrosating agent for diethanolamine: A model study

Schmeltz, I.; Wenger, Allison

doi:10.1016/0015-6264(79)90206-2

Cited by 29 publications

(4 citation statements)

References 8 publications

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“…The decomposition of Bronopol in cosmetic formulations is a complex reaction leading to many products, and its rate is strongly dependent on the pH of the system. Bronopol is much more stable in acidic environments but at basic pH the reaction appears to be catalysed by the formation of formaldehyde as an initial produci (4,5). Although not considered to be a primary decomposition product of Bronopol, high levels (mg kg-') of free nitrite have been detected in cosmetic formulations preserved with 0.01% Bronopol.…”

Section: Discussionmentioning

confidence: 99%

Study of the fate of Bronopol and the effects of antioxidants on N‐nitrosamine formation in shampoos and skin creams

Dunnett

Telling

1984

Intern J of Cosmetic Sci

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Synopsis The role of antioxidants in preventing nitrosamine (N-nitroso diethanolamine) formation in shampoos and skin creams and the levels of Bronopol (2-bromo, 2-nitropropane-1, 3-diol) addition in relation to the resultant levels of N-nitroso compounds have been studied. The addition of 0.05% BHT, alpha-tocopherol or ascorbate was effective in preventing nitrosamine formation (limit of determination: 2.5 mug kg(-1)) in products preserved with 0.01% Bronopol. At 0.05% Bronopol, 0.2% of all three antioxidants was effective in preventing nitrosamine formation but at 0.1% Bronopol only alpha-tocopherol was effective. Levels of Bronopol found in shampoo formulations stored for 2 weeks at 37 degrees C with initial concentrations of 0.005-0.1% were reduced by 64-86%, independent of the initial concentration. The levels in skin creams stored for extended periods at ambient temperature with 0.01% Bronopol initially were reduced by, on average, 60%. High nitrite levels (NO(2) (-)) were found in formulations containing 0.01% Bronopol but no antioxidants (200-250 mg kg(-1)). Detected levels of nitrite in skin cream formulations were greater than could be formed by stoichiometric decomposition of Bronopol. In formulations with both Bronopol and antioxidants the levels of nitrite were considerably reduced. When alpha-tocopherol rather than BHT or ascorbate was the antioxidant then the nitrite levels were appreciably higher but formation of N-nitroso diethanolamine was no greater. High nitrite levels correlated with the formation of detectable levels of N-nitroso compounds in the absence of antioxidants.

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Section: Discussionmentioning

confidence: 99%

Study of the fate of Bronopol and the effects of antioxidants on N‐nitrosamine formation in shampoos and skin creams

Dunnett

Telling

1984

Intern J of Cosmetic Sci

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“…In some cases, nitrosamines are formed by the nitrosation of the primary component of the raw material while, in others, nitrosamines are formed from the nitrosation of other amines present in the raw material as contaminants. The tertiary amine triethanolamine (TEA) nitrosates rather slowly (25). However, the cosmetic raw material TEA typically contains the secondary amine diethanolamine (DEA) as a contaminant.…”

Section: Formation Of Nitrosamines In Cosmetic Productsmentioning

confidence: 99%

Nitrosamines in Sunscreens and Cosmetic Products

Havery¹,

Chou²

1994

ACS Symposium Series

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Several nitrosamines, most of which have been shown to be carcinogenic in laboratory animals, have been identified in cosmetic products over the last fifteen years. These compounds are primarily formed from amine precursors and nitrosating agents in the cosmetic product but are also introduced into the product through cosmetic raw materials. Market surveys of sunscreens and cosmetics have revealed levels of nitrosodiethanolamine up to 45 ppm and levels of 2-ethylhexyl 4-(N-methyl-N-nitrosamino) benzoate up to 21 ppm. Results from market surveys of cosmetic products over the past fifteen years do not suggest any trend in the nitrosamine levels in these products. A summary of the occurrence and levels of nitrosamines in cosmetic products along with strategies for the reduction or elimination of these compounds is presented.The presence of nitrosamines has been reported in a number of consumer products including bacon, beer, rubber nipples and pacifiers, pesticides, drugs, tobacco and cutting fluids (1-10). Nitrosamines were first reported in cosmetic products in 1977 when Fan et al. (11) described _ the presence of nitrosodiethanolamine in products such as lotions, shampoos, and cosmetics.Most nitrosamines that have been tested have been found to be carcinogenic in laboratory animals (12-16). However, the potential health significance of the presence of nitrosamines in cosmetic products depends on several factors. These include the specific nitrosamine involved (carcinogenic potency), the level of contamination, the type of product (i.e.. creams and lotions versus wash-off products), the frequency of use, the degree of absorption through the skin, and nitrosamine stability (exposure to UV light). This paper reviews the current knowledge about the formation and occurrence of nitrosamines in This chapter not subject to U.S.

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“…However, such promotion may not be characteristic of transition metal complexes in general, since ferric yanide ion has been shown to promote nitrosation in metalworking fluids, whereas ferric EDTA does not (20) structurally similar to tris nitro is bronopol, which is widely used in cosmetics and shampoos. A feature common to these compounds is the C-nitro group, which is also thought to release nitrite (30). In the presence of amines, C-nitro compounds are indeed nitrosating agents, and their nitrosation potential increases with addition of electronwithdrawing groups (31).…”

Section: Chemical Complexes Of Various Transition Metals Have Been Shmentioning

confidence: 99%

Effects of TSCA on the Metalworking Fluids Industry: Increased Awareness of Nitrosamine Contamination

Fribush

1983

TSCA's Impact on Society and Chemical Industry

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2-bromo-2-nitropropane-1,3-diol as a nitrosating agent for diethanolamine: A model study

Cited by 29 publications

References 8 publications

Study of the fate of Bronopol and the effects of antioxidants on N‐nitrosamine formation in shampoos and skin creams

Study of the fate of Bronopol and the effects of antioxidants on N‐nitrosamine formation in shampoos and skin creams

Nitrosamines in Sunscreens and Cosmetic Products

Effects of TSCA on the Metalworking Fluids Industry: Increased Awareness of Nitrosamine Contamination

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