Hydroxymethylpentylcyclohexenecarboxaldehyde

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HydroxymethylpentylTemplate:Shycyclohexenecarboxaldehyde[1]
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Density 0.995 g/mL at 20 °C

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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[2] 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.[3] It is commonly tested for in patients undergoing patch testing.[4]

References

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  1. 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde at Sigma-Aldrich
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  3. Allergens in Cosmetics & Personal Care Products
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