Metalloporphyrin-catalyzed oxidations 3. Expoxidation and aldehyde formation by oxidative carboncarbon bond cleavage in squalene

Fuhrhop, Jürgen‐Hinrich; Baccouche, Mohamed; Penzlin, Gustav

doi:10.1016/0304-5102(80)85023-1

Cited by 15 publications

(4 citation statements)

References 12 publications

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“…Compound D appeared as a yellowish and highly viscous material (viscosity 26 2 cp at 30 C; squalene has a viscosity of 115 cp at same temperature), and its NMR spectrum revealed a polymeric form of the squalene unit in which the double-bonds had been substituted by aldehyde, ketone and hydroxyl groups. This is in agreement with the findings of Furhop, Baccouche & Penzlin (1980). Application of compound D to rabbit ears confirmed its ability to induce comedones, in contrast to pure non-oxidized squalene, which did not.…”

Section: Resultssupporting

confidence: 91%

A possible role for squalene in the pathogenesis of acne. I. In vitro study of squalene oxidation

Saint‐Léger

Bagué

Cohen³

et al. 1986

Br J Dermatol

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An in vitro study of the oxidation of squalene, and a description of factors acting on this transformation are presented. Thin layer chromatography was used to quantify the products generated by different oxidation processes. The results clearly show that squalene is a highly effective oxygen-scavenging agent. Its oxidation may first induce comedogenesis and, as a secondary event, cause a large reduction in oxygen tension in the human pilo-sebaceous duct. Porphyrins were confirmed to be highly efficient catalytic factors in the squalene oxidation process. The relationships between comedogenesis, bacterial colonization, and the role of sebum in the pathogenesis of acne are discussed in the light of these findings.

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Section: Resultssupporting

confidence: 91%

A possible role for squalene in the pathogenesis of acne. I. In vitro study of squalene oxidation

Saint‐Léger

Bagué

Cohen³

et al. 1986

Br J Dermatol

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“…As a matter of fact, many activities appear centred towards oxygen and its control within the follicular canal, where are found various porphyrins [3,[15][16][17], synthesized by Propionibacteria spp. Porphyrins are highly efficient photocatalytic pigments in the presence of oxygen.…”

Section: Sebum Squalene and Skin Floramentioning

confidence: 99%

Oxidization of squalene, a human skin lipid: a new and reliable marker of environmental pollution studies

Pham

Boussouira

Moyal

et al. 2015

Intern J of Cosmetic Sci

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Synopsis A review of the oxidization of squalene, a specific human compound produced by the sebaceous gland, is proposed. Such chemical transformation induces important consequences at various levels. Squalene by‐products, mostly under peroxidized forms, lead to comedogenesis, contribute to the development of inflammatory acne and possibly modify the skin relief (wrinkling). Experimental conditions of oxidation and/or photo‐oxidation mechanisms are exposed, suggesting that they could possibly be bio‐markers of atmospheric pollution upon skin. Ozone, long UVA rays, cigarette smoke… are shown powerful oxidizing agents of squalene. Some in vitro, ex vivo and in vivo testings are proposed as examples, aiming at studying ingredients or products capable of boosting or counteracting such chemical changes that, globally, bring adverse effects to various cutaneous compartments.

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“…Firstly, it must be shown that it is not a computational artifact but rather a chemical trend that emerges from the broader context of chemistry. Secondly, the conclusion must be harmonized with various properties, such as the special thermochemical stability of benzene (2), the substantial rotational barrier of allyl radical (1), and so on.…”

mentioning

confidence: 99%

Is delocalization a driving force in chemistry? Benzene, allyl radical, cyclobutadiene, and their isoelectronic species

Shaik¹,

Hiberty²,

Lefour³

et al. 1987

J. Am. Chem. Soc.

242

153

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Metalloporphyrin-catalyzed oxidations 3. Expoxidation and aldehyde formation by oxidative carboncarbon bond cleavage in squalene

Cited by 15 publications

References 12 publications

A possible role for squalene in the pathogenesis of acne. I. In vitro study of squalene oxidation

A possible role for squalene in the pathogenesis of acne. I. In vitro study of squalene oxidation

Oxidization of squalene, a human skin lipid: a new and reliable marker of environmental pollution studies

Is delocalization a driving force in chemistry? Benzene, allyl radical, cyclobutadiene, and their isoelectronic species

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