Hydroxymethylpentylcyclohexenecarboxaldehyde

{{chembox

| Name=Hydroxymethylpentyl{{shy}}cyclohexenecarboxaldehyde

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 417597475

| Reference=[http://www.sigmaaldrich.com/catalog/search/ProductDetail/aldrich/95594 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde] at Sigma-Aldrich

| ImageFile=Lyral Strukturformel.svg

| ImageSize=200px

| PIN=4-(4-Hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde

| OtherNames=Lyral, Kovanol, Mugonal, Landolal

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=31906-04-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = QUE43B9Z2Q

| EINECS = 250-863-4

| PubChem=91604

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 82714

| SMILES = O=CC1C/C=C(/CCCC(O)(C)C)CC1

| 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

| InChIKey = ORMHZBNNECIKOH-UHFFFAOYAY

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ORMHZBNNECIKOH-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=13 | H=22 | O=2

| Appearance=

| Density=0.995 g/mL at 20 °C

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|Section3={{Chembox Hazards

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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{{cite encyclopedia |author1=Fahlbusch, K.-G. |author2=Hammerschmidt, F.-J. |author3=Panten, J. |author4=Pickenhagen, W. |author5=Schatkowski, D. |author6=Bauer, K. |author7=Garbe, D. |author8=Surburg, H. | encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry | year = 2002 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a11_141 |chapter=Flavors and Fragrances |isbn=3527306730}} 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.[http://www.cromlab.es/Articulos/Catalogos/Catalogos_AccuStandard/Accu_Allergene%20in%20Cosmetics.pdf Allergens in Cosmetics & Personal Care Products] It is commonly tested for in patients undergoing patch testing.{{cite journal |last1=Bruze |first1=Magnus |last2=Andersen |first2=Klaus Ejner |last3=Goossens |first3=An |title=Recommendation to include fragrance mix 2 and hydroxyisohexyl 3-cyclohexene carboxaldehyde (Lyral) in the European baseline patch test series |journal=Contact Dermatitis |date=March 2008 |volume=58 |issue=3 |pages=129–133 |doi=10.1111/j.1600-0536.2007.01292.x|pmid=18279149 |s2cid=205813259 |url=https://lirias.kuleuven.be/handle/123456789/379411 }}

References