Hydroxymethylpentylcyclohexenecarboxaldehyde

Hydroxymethylpentyl­cyclohexenecarboxaldehyde

File:Lyral Strukturformel.svg
Names
Preferred IUPAC name 4-(4-Hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde
Other names Lyral, Kovanol, Mugonal, Landolal
Identifiers
CAS Number	31906-04-4 Error creating thumbnail: Y
3D model (JSmol)	Interactive image
ChemSpider	82714 ☒N
ECHA InfoCard
EC Number	250-863-4
E number
PubChem CID	91604
UNII	QUE43B9Z2Q Error creating thumbnail: Y
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C13H22O2/c1-13(2,15)9-3-4-11-5-7-12(10-14)8-6-11/h5,10,12,15H,3-4,6-9H2,1-2H3 ☒N Key: ORMHZBNNECIKOH-UHFFFAOYSA-N ☒N InChI=1/C13H22O2/c1-13(2,15)9-3-4-11-5-7-12(10-14)8-6-11/h5,10,12,15H,3-4,6-9H2,1-2H3 Key: ORMHZBNNECIKOH-UHFFFAOYAY
SMILES O=CC1C/C=C(/CCCC(O)(C)C)CC1
Properties
Chemical formula	C13H22O2
Molar mass	210.317 g·mol−1
Density	0.995 g/mL at 20 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is Error creating thumbnail: Y☒N ?) Infobox references

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.