“Hydroxymethylpentylcyclohexenecarboxaldehyde”的意思、由来-开放百科全书

词条

Hydroxymethylpentylcyclohexenecarboxaldehyde

释义

Synthesis
Safety
References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 417597475
| Reference=^[1]
| ImageFile=Lyral.png
| ImageSize=200px
| IUPACName=4-(4-Hydroxy-4-methylpentyl)-1-cyclohex-3-enecarboxaldehyde
| OtherNames=Lyral, Kovanol, Mugonal, Landolal
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=31906-04-4
| 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
| MeltingPt=
| BoilingPt=
| Solubility=
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}

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^[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'. Oxidation 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

1. ^4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde at Sigma-Aldrich
2. ^{{ cite encyclopedia |author1=Fahlbusch, K.-G. |title=Ullmann's Encyclopedia of Industrial Chemistry |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 }}
3. ^Allergens in Cosmetics & Personal Care Products
4. ^{{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}}

4 : Perfume ingredients|Aldehydes|Alcohols|Cyclohexenes

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