Helional

Helional
Names
	IUPAC name 3-(1,3-Benzodioxol-5-yl)-2-methylpropanal
	Other names 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal;; 2-piperonylpropanal; Helional; Ocean propanal
Identifiers
CAS Number	1205-17-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	58337;
ECHA InfoCard	100.013.528
PubChem CID	64805;
UNII	L65EG8H6PA ;
CompTox Dashboard (EPA)	DTXSID7043908 ;
	InChI InChI=1S/C11H12O3/c1-8(6-12)4-9-2-3-10-11(5-9)14-7-13-10/h2-3,5-6,8H,4,7H2,1H3 Key: BOPPSUHPZARXTH-UHFFFAOYSA-N; InChI=1/C11H12O3/c1-8(6-12)4-9-2-3-10-11(5-9)14-7-13-10/h2-3,5-6,8H,4,7H2,1H3 Key: BOPPSUHPZARXTH-UHFFFAOYAR;
	SMILES CC(CC1=CC2=C(C=C1)OCO2)C=O;
Properties
Chemical formula	C11H12O3
Molar mass	192.214 g·mol−1
Appearance	Colorless liquid
Odor	floral, herbaceous
Density	1.162 g/cm3
Boiling point	282 °C (540 °F; 555 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
Safety data sheet (SDS)
Legal status	BR: Class D1 (Drug precursors);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Helional (from heliotropin, from which is it commonly derived) is a chemical compound used as a perfume in soap and laundry detergent. Chemically it is an aldehyde with a hydrocinnamaldehyde motif; a structural element which is present in a number of other important commercial fragrances and odorants.^[3]

Synthesis

Several synthetic routes exist but the most common is a crossed-aldol condensation between piperonal (heliotropin) and propanal followed by selective hydrogenation of the intermediate alkene. This produces a racemic product.

References

^ Sigma-Aldrich Co., 2-methyl-3-(3,4-methylenedioxyphenyl)propanal. Retrieved on 2016-03-02.
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ Wetzel, Christian H.; Oles, Markus; Wellerdieck, Christiane; Kuczkowiak, Michael; Gisselmann, Gunter; Hatt, Hanns (1999). "Specificity and sensitivity of a human olfactory receptor functionally expressed in human embryonic kidney 293 cells and Xenopus laevis oocytes". Journal of Neuroscience. 19 (1): 7426–7433. doi:10.1093/chemse/bji002. PMID 15647465.

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[sigma-1] Sigma-Aldrich Co., 2-methyl-3-(3,4-methylenedioxyphenyl)propanal. Retrieved on 2016-03-02.

[2] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[3] Wetzel, Christian H.; Oles, Markus; Wellerdieck, Christiane; Kuczkowiak, Michael; Gisselmann, Gunter; Hatt, Hanns (1999). "Specificity and sensitivity of a human olfactory receptor functionally expressed in human embryonic kidney 293 cells and Xenopus laevis oocytes". Journal of Neuroscience. 19 (1): 7426–7433. doi:10.1093/chemse/bji002. PMID 15647465.

[3]

[1]

[2]

Helional

Synthesis

See also

References