4- (4-Hydroxy-4-methylpentyl) cyclohex-3-ene-1-carbaldehyde

Structural formula
Simplified structural formula without stereochemistry
General
Surname	4- (4-Hydroxy-4-methylpentyl) cyclohex-3-ene-1-carbaldehyde
other names	HICC HYDROXYISOHEXYL 3-CYCLOHEXENE CARBOXALDEHYDE ( INCI ) Lyral
Molecular formula	C 13 H 22 O 2
Brief description	colorless liquid
External identifiers / databases
CAS number 31906-04-4 EC number 250-863-4 ECHA InfoCard 100.046.225 PubChem 91604 Wikidata Q5955634
properties
Molar mass	210.32 g mol −1
Physical state	liquid
density	0.995 g cm −3 (20 ° C)
boiling point	318 ° C
solubility	practically insoluble in water (135 mg l −1 at 20 ° C)
Refractive index	1.527
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 317-412 P: ?
Toxicological data	3230 mg kg −1 ( LD 50 ,  rat ,  oral ) 11200 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

4- (4-Hydroxy-4-methylpentyl) cyclohex-3-en-1-carbaldehyde is a chemical compound from the group of substituted aldehydes . However, the technical product of the compound is not a pure substance, but a mixture with 3- (4-hydroxy-4-methylpentyl) cyclohex-3-ene carbaldehyde.

Extraction and presentation

4- (4-Hydroxy-4-methylpentyl) cyclohex-3-en-1-carbaldehyde can be obtained from myrcenol and acrolein in the presence of zinc chloride by the Diels-Alder reaction .

properties

4- (4-Hydroxy-4-methylpentyl) cyclohex-3-en-1-carbaldehyde is a viscous colorless liquid. The substance has a sweetish scent that is perceived as lily of the valley .

use

4- (4-Hydroxy-4-methylpentyl) cyclohex-3-en-1-carbaldehyde is used as a fragrance in fine perfumes, household items, soaps and deodorants.

safety instructions

The numerous clinical positive results obtained in the patch test indicate that the compound has a skin-sensitizing potential. The results of animal experiments cannot be clearly assessed.

Individual evidence

1. ↑ Entry on HYDROXYISOHEXYL 3-CYCLOHEXENE CARBOXALDEHYDE in the CosIng database of the EU Commission, accessed on December 29, 2019.
2. ↑ ^{a b c d e f} Entry on 4- (4-Hydroxy-4-methylpentyl) cyclohex-3-en-1-carbaldehyde in the GESTIS substance database of the IFA , accessed on April 22, 2018(JavaScript required) .
3. ↑ Data sheet 4- (4-Hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde, mixture of isomers, ≥97.0% (GC) from Sigma-Aldrich , accessed on April 22, 2018 ( PDF ).
4. ↑ ^{a b} Source: Opinion on Hydroxyisohexyl 3-cyclohexene carboxaldehyde , December 13-14, 2011.
5. ↑ Echa: CLH REPORT FOR HYDROXYISOHEXYL 3-CYCLOHEXENE CARBOXALDEHYDE (HICC) , accessed on April 22, 2018.
6. ↑ Entry on 4- (4-hydroxy-4-methylpentyl) cyclohex-3-ene-1-carbaldehyde in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 23, 2018. Manufacturers or distributors can use the harmonized classification and expand labeling .
7. ↑ External identifiers of or database links for 3- (4-hydroxy-4-methylpentyl) cyclohex-3-ene-carbaldehyde : CAS number: 51414-25-6, EC number: 257-187-9, ECHA InfoCard : 100.051.971 , PubChem : 162105 , ChemSpider : 142367 , Wikidata : Q81984943 .
8. ↑ ^{a b c} Hydroxymethylpentylcyclohexencarboxaldehyd (Lyral) [MAK Value Documentation in German language, 2004]. In The MAK Collection for Occupational Health and Safety. (2012). doi : 10.1002 / 3527600418.mb3190604d0039 .
9. ↑ JD Johansen, PJ Frosch, C. Svedman, KE Andersen, M. Bruze, C. Pirker, T. Menné: Hydroxyisohexyl 3-cyclohexene carboxaldehyde-known as Lyral: quantitative aspects and risk assessment of an important fragrance allergen. In: Contact Derm. 48, 2003, pp. 310-316, PMID 14531869 .
10. ^ BM Hausen, Sabine Bottenbruch: Lyral allergy. In: Current Dermatology. 27, p. 310, doi : 10.1055 / s-2001-18673 .