Introduction of a methoxymethyl side chain into p-phenylenediamine attenuates its sensitizing potency and reduces the risk of allergy induction

Goebel, Carsten; Troutman, John; Hennen, Jenny; Rothe, Helga; Schlatter, Harald; Gerberick, G. Frank; Blömeke, Brunhilde

doi:10.1016/j.taap.2013.11.016

Cited by 51 publications

(66 citation statements)

References 39 publications

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“…Goebel et al describe experiments in which altering the molecular structure of PPD by the addition of a methoxymethyl side chain (ME-PPD) resulted in a decrease in the molecule's skin sensitizing ability in vitro and in vivo. These molecular changes did not significantly alter hair dyeing properties of PPD [43]. If fewer people become sensitized to hair dye then, in theory, we may see less elicitation from disperse textile dyes via cross-reaction.…”

Section: Allergic Contact Dermatitismentioning

confidence: 80%

The Role of Textiles in Dermatitis: An Update

Mobolaji-Lawal

Nedorost

2015

Curr Allergy Asthma Rep

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Dermatitis has important implications for individuals who are affected. It can significantly impair function and quality of life. Dermatitis is multi-factorial and often includes elements of atopic dermatitis, allergic contact dermatitis, and irritant contact dermatitis in a co-existent manner. Textiles are in contact with the human skin for extended periods of time and as a result, they are an important part of the cutaneous environment. Thus, it is not surprising that textiles play a major role in both the etiology and the treatment of various types of dermatitis. This review discusses the role of textiles in dermatitis with an emphasis on interesting and recent advances, trends, perspectives, gaps, and conflicts in the field. In addition, we mention other disease processes to be aware of as they can often mimic textile pattern dermatitis. Lastly, we provide a diagnostic approach for patients presenting with textile pattern dermatitis.

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Section: Allergic Contact Dermatitismentioning

confidence: 80%

The Role of Textiles in Dermatitis: An Update

Mobolaji-Lawal

Nedorost

2015

Curr Allergy Asthma Rep

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“…With the introduction of ME‐PPD into commercial hair dye products, a PPD/PTD alternative has become available that is considered to avoid de novo generation of hair dye contact allergy for hair dye users . However, despite warnings not to use ME‐PPD hair colorants in case of hair dye allergy, individuals with existing allergy to PPD and/or PTD are still likely considering the use of ME‐PPD‐containing hair dye products as an alternative.…”

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

“…Following the idea of primary prevention of skin sensitization and the onset of contact dermatitis, the recently developed precursor 2‐methoxymethyl (ME)‐PPD provides excellent hair colouring performance with significantly lower skin‐sensitizing properties compared with PPD or the structurally related compound PTD (for the chemical structures see Fig. ) . Consequently, based on the available preclinical data, the risk of allergic induction through ME‐PPD is considered very low for hair dye consumers because the maximal on‐head exposure is more than 100‐fold lower than the allergy induction threshold (8·8 vs. 1075 μg cm 2 ).…”

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confidence: 99%

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Continuous usage of a hair dye product containing 2‐methoxymethyl‐para‐phenylenediamine by hair‐dye‐allergic individuals

et al. 2016

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Funding sourcesNone. Conflicts of interest SummaryBackground Despite a positive patch test reaction to para-phenylenediamine (PPD) and/or toluene-2,5-diamine (PTD), many people attempt to continue dyeing their hair with products containing PPD or its derivatives. Objectives Investigation of elicitation reactions among PPD/PTD-allergic individuals to hair dye products containing the less sensitizing PPD derivative 2-methoxymethyl (ME)-PPD. Methods Elicitation reactions were studied in 43 PPD/PTD-allergic individuals by a 45-min pretest with an ME-PPD-containing hair dye on their forearm. Upon a negative result this was followed by exposure to subsequent hair colour treatment(s). Results Overall, 38 of 43 PPD/PTD-allergic individuals did not develop an elicitation reaction during the pretest with ME-PPD-containing hair dye products, and were eligible for subsequent hair colour treatments. Of these 38 PPD/PTD-allergic individuals, 29 tolerated subsequent hair dyeing with ME-PPD-containing hair dye products, while seven showed mild and two showed moderate/marked allergic reactions upon the first hair colour treatment. Conclusions Hair dye products with the less sensitizing ME-PPD were tolerated by 29 of 43 (67%) PPD/PTD-allergic individuals throughout continued hair dyeing with an average of nine treatments per year. Five individuals reacted upon pretesting, while only mild-to-moderate/marked skin reactions occurred upon hair dyeing in nine individuals who were not identified by the pretest. To our knowledge this is the first study among PPD/PTD-allergic individuals indicating that a negative 45-min pretest with a hair dye product helps to avoid severe allergic reactions.

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“…However, the haircolor industry has been successful in replacing materials of concern over the past 40 years in its drive for improved performance and safety in hair dye chemistry. For example, we have recently developed and commercialized 2‐(methoxymethyl)benzene‐1,4‐diamine ( 8 ) as a primary intermediate that replaces 1 and 7 and that offers reduced allergenic potential .…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Insights into Substituent Effects on Reactivity of 2‐(Methoxymethyl)benzene‐1,4‐diamine

Bailey

Zhang

Murphy

2017

Int J of Chemical Kinetics

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In the series of benzene‐1,4‐diamines (p‐phenylenediamines) investigated, 2‐(methoxymethyl)benzene‐1,4‐diamine (2‐methoxymethyl‐p‐phenylenediamine) is the most slowly oxidized, with removal of the first electron being rate determining. This electron‐withdrawing methoxymethyl group also drove a faster coupling step with 3‐aminophenol (m‐aminophenol) than for the analogs with electron‐donating groups. However, the series parent, benzene‐1,4‐diamine, exhibited the fastest coupling step. Since both N(1) and N(4) of the primary intermediates react with m‐aminophenol, it seems that steric hindrance by the 2‐substituents slows the overall rate. When 3‐amino‐2,6‐dimethylphenol is the coupler, the kinetics are biphasic. Nonproductive adducts are formed reversibly with all the primary intermediates by ipso attack at C(6). For 2‐(methoxymethyl)benzene‐1,4‐diamine, formation of this nonproductive adduct is favored more than for the other compounds in the series, in what seems to be a kinetically rather than thermodynamically controlled process. This slows the overall rate of color formation.

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Introduction of a methoxymethyl side chain into p-phenylenediamine attenuates its sensitizing potency and reduces the risk of allergy induction

Cited by 51 publications

References 39 publications

The Role of Textiles in Dermatitis: An Update

The Role of Textiles in Dermatitis: An Update

Continuous usage of a hair dye product containing 2‐methoxymethyl‐para‐phenylenediamine by hair‐dye‐allergic individuals

Mechanistic Insights into Substituent Effects on Reactivity of 2‐(Methoxymethyl)benzene‐1,4‐diamine

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