Photooxidation with Simultaneous Reduction of Hydroperoxides with Tetrabutylammonium Borohydride. Synthesis of Perillenal from Myrcene.

Bæckström, Peter; Okecha, S. A.; Silva, N. De; Norin, Torbjörn; Wijekoon, Donald; Ulff, Bengt

doi:10.3891/acta.chem.scand.36b-0031

Cited by 37 publications

(10 citation statements)

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“…Whether there is any oxidized linalool in the preparation is unknown, but the oxidation products usually are found in the air‐exposed fragrances and raw terpene preparations, 76‐78 so the probability is high. Singlet oxygen, produced during photocontact sensitization to ketoprofen, may be contributing to the oxidation of linalool and limonene by formation of allylic peroxides 79,80 . However, limonene is not present in Orudis, and neither linalool nor limonene are present in the other two ketoprofen gels, present on the Swedish market at the time for possible sensitization of our patients.…”

Section: Discussionmentioning

confidence: 84%

“…Singlet oxygen, produced during photocontact sensitization to ketoprofen, may be contributing to the oxidation of linalool and limonene by formation of allylic peroxides. 79,80 However, limonene is not present in Orudis, and neither linalool nor limonene are present in the other two ketoprofen gels, present on the Swedish market at the time for possible sensitization of our patients. Simultaneous exposure to other skincare products containing terpenes, either already oxidized or oxidized in the presence of ketoprofen, needs to be looked further into.…”

Section: Foti Et Al Have By Means Of Computerized Conformational Anal...mentioning

confidence: 90%

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Contact allergy to fragrance mix I and its components in individuals with photocontact allergy to ketoprofen

et al. 2021

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Background: Contact allergy to fragrance mix I (FM I) is over-represented in patients photoallergic to ketoprofen. The prevalence of contact allergy to two components of FM I, cinnamal and cinnamyl alcohol, in ketoprofen-photoallergic patients is higher than in dermatitis patients.Objective: To explore the prevalence of contact allergy to FM I and its individual components in patients with photocontact allergy to ketoprofen, and to compare with a dermatitis and the general population.Methods: Data on patch and photopatch tests performed between 2009-2018 were collected. Ketoprofen-photoallergic patients were compared with dermatitis patients and published data on the general population regarding the prevalence and the distribution of contact allergy to FM I and its components.Results: A higher prevalence of contact allergy to cinnamyl alcohol compared with cinnamal (23.3% vs 10.0%), and eugenol compared with isoeugenol (23.3% vs 6.7%), was observed in ketoprofen-photoallergic patients, while the relationship was the opposite in the dermatitis group (0.7% vs 1.05%; 0.4% vs 0.9%). The overall prevalence of contact allergy to several components of FM I was significantly higher in ketoprofen-photoallergic patients.Conclusions: Contact allergy to FM I and many of its components is over-represented in patients photoallergic to ketoprofen compared with dermatitis patients and the general population.

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Section: Discussionmentioning

confidence: 84%

Section: Foti Et Al Have By Means Of Computerized Conformational Anal...mentioning

confidence: 90%

Contact allergy to fragrance mix I and its components in individuals with photocontact allergy to ketoprofen

et al. 2021

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“…7‐Hydroperoxy‐3,7‐dimethylocta‐1,5‐diene‐3‐yl acetate (3) and 6‐hydroperoxy‐3,7‐dimethylocta‐1,7‐diene‐3‐yl acetate (4) . Linalyl acetate (0.8 g, 4.1 mmol) was added to a CHCl 3 solution of tetrabutylammonium salt of Bengal rose, prepared according to a procedure described by Bäckström et al (11). The solution was irradiated for 6 hr using a Rayonet reactor and a constant flow of oxygen.…”

Section: Methodsmentioning

confidence: 99%

Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens

2007

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“…1). The photo-oxidation reaction was performed as previously described (21). Starting from citronellol (0.794 g, 5.1 mmol) and after a reaction time of 3 hr, the crude product was purified by flash chromatography (ethyl acetate/hexane, 2:3).…”

Section: -Hydroperoxy-37-dimethyloct-7-ene-1-ol (2) and (E)-7hydropmentioning

confidence: 99%

Characterization of skin sensitizers from autoxidized citronellol – impact of the terpene structure on the autoxidation process

et al. 2014

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The present study shows the impact of the absence of the 2,3-double bond in the citronellol structure on the oxidation pathways for formation of oxidation products. The study also shows the usefulness of our new GC-MS method for quantification of the citronellol oxidation products, especially the hydroperoxides. The investigated citronellol hydroperoxides could be important allergens, owing to the high concentrations detected and frequent exposure to citronellol in the population.

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Photooxidation with Simultaneous Reduction of Hydroperoxides with Tetrabutylammonium Borohydride. Synthesis of Perillenal from Myrcene.

Cited by 37 publications

References 0 publications

Contact allergy to fragrance mix I and its components in individuals with photocontact allergy to ketoprofen

Contact allergy to fragrance mix I and its components in individuals with photocontact allergy to ketoprofen

Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens

Characterization of skin sensitizers from autoxidized citronellol – impact of the terpene structure on the autoxidation process

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