Helional

{{Chembox

| ImageFile = Ocean propanal.svg

| ImageSize = 200px

| ImageClass = skin-invert

| IUPACName = 3-(1,3-Benzodioxol-5-yl)-2-methylpropanal

| OtherNames = 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal;
2-piperonylpropanal
Helional
Ocean propanal

|Section1={{Chembox Identifiers

| CASNo = 1205-17-0

| CASNo_Ref = {{cascite|correct|CAS}}

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

| UNII = L65EG8H6PA

| PubChem = 64805

| ChemSpiderID = 58337

| SMILES = CC(CC1=CC2=C(C=C1)OCO2)C=O

| 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

| InChIKey = BOPPSUHPZARXTH-UHFFFAOYAR

| StdInChI = 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

| StdInChIKey = BOPPSUHPZARXTH-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=11|H=12|O=3

| Appearance = Colorless liquid

| Odor = floral, herbaceous

| Density = 1.162 g/cm3

| MeltingPt =

| BoilingPtC = 282

| Solubility =

}}

|Section3={{Chembox Hazards

| ExternalSDS = {{Sigma-Aldrich|id=W523909|name=2-methyl-3-(3,4-methylenedioxyphenyl)propanal|accessdate=2016-03-02}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|305+351+338}}

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

|Section4={{Chembox Legal status

| legal_AU =

| legal_BR = D1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_US =

| legal_UK =

| legal_UN =

}}

}}

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.{{cite journal|title=Specificity and sensitivity of a human olfactory receptor functionally expressed in human embryonic kidney 293 cells and Xenopus laevis oocytes|author1=Wetzel, Christian H. |author2=Oles, Markus |author3=Wellerdieck, Christiane |author4=Kuczkowiak, Michael |author5=Gisselmann, Gunter |author6=Hatt, Hanns |journal=Journal of Neuroscience|year=1999|volume=19|issue=1|pages=7426–7433|doi=10.1093/chemse/bji002|pmid=15647465|doi-access=free}}

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.

See also

References