Hydroxymethylpentylcyclohexenecarboxaldehyde

Hydroxymethylpentylcyclohexenecarboxaldehyde¹
	source ↗
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 Y;
3D model (JSmol)	Interactive image;
ChemSpider	82714 N;
ECHA InfoCard	100.046.225
EC Number	250-863-4;
PubChem CID	91604;
UNII	QUE43B9Z2Q Y;
CompTox Dashboard (EPA)	DTXSID1027970 ;
	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 YN ?) 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 myrcene² 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

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

[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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