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Hydroxymethylpentylcyclohexenecarboxaldehyde

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(Redirected from Lyral)
Hydroxymethylpentyl­cyclohexenecarboxaldehyde
Names
Preferred IUPAC name 4-(4-Hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde
Other names Lyral, Kovanol, Mugonal, Landolal
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.046.225 Edit this at Wikidata
EC Number
  • 250-863-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H22O2/c1-13(2,15)9-3-4-11-5-7-12(10-14)8-6-11/h5,10,12,15H,3-4,6-9H2,1-2H3Key: ORMHZBNNECIKOH-UHFFFAOYSA-N
  • InChI=1/C13H22O2/c1-13(2,15)9-3-4-11-5-7-12(10-14)8-6-11/h5,10,12,15H,3-4,6-9H2,1-2H3Key: ORMHZBNNECIKOH-UHFFFAOYAY
SMILES
  • O=CC1C/C=C(/CCCC(O)(C)C)CC1
Properties
Chemical formula C13H22O2
Molar mass 210.317 g·mol
Density 0.995 g/mL at 20 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Hydroxymethylpentylcyclohexenecarboxaldehyde 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

  1. 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde at Sigma-Aldrich
  2. Fahlbusch, K.-G.; Hammerschmidt, F.-J.; Panten, J.; Pickenhagen, W.; Schatkowski, D.; Bauer, K.; Garbe, D.; Surburg, H. (2002). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_141. ISBN 3527306730.
  3. Allergens in Cosmetics & Personal Care Products
  4. Bruze, Magnus; Andersen, Klaus Ejner; Goossens, An (March 2008). "Recommendation to include fragrance mix 2 and hydroxyisohexyl 3-cyclohexene carboxaldehyde (Lyral) in the European baseline patch test series". Contact Dermatitis. 58 (3): 129–133. doi:10.1111/j.1600-0536.2007.01292.x. PMID 18279149. S2CID 205813259.
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