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Hydroxymethylpentylcyclohexenecarboxaldehyde

Hydroxymethylpentylcyclohexenecarboxaldehyde (HMPCC) is a synthetic fragrance known by the trade names Lyral, Kovanol, Mugonal, Landolal. It is found in some soaps, eau de toilettes, aftershaves and deodorants.

Synthesis

Typical synthesis starts from myrcene and involves a Diels–Alder reaction with acrolein to produce the cyclohexenecarbaldehyde group, this species is marketed as a fragrance in its own right, most commonly under the name 'myrac aldehyde'. Acid-catalyzed hydration of this completes the synthesis by forming the tertiary alcohol.

Safety

Lyral is known to act as a skin allergen and is listed as such in EU Directive 76/768/EEC. It is commonly tested for in patients undergoing patch testing.

References

References

  1. [http://www.sigmaaldrich.com/catalog/search/ProductDetail/aldrich/95594 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde] at [[Sigma-Aldrich]]
  2. {{cite encyclopedia. (2002). Wiley-VCH
  3. [http://www.cromlab.es/Articulos/Catalogos/Catalogos_AccuStandard/Accu_Allergene%20in%20Cosmetics.pdf Allergens in Cosmetics & Personal Care Products]
  4. (March 2008). "Recommendation to include fragrance mix 2 and hydroxyisohexyl 3-cyclohexene carboxaldehyde (Lyral) in the European baseline patch test series". Contact Dermatitis.
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perfume-ingredients aldehydes tertiary-alcohols cyclohexenes
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