Jasminaldehyde

Jasminaldehyde
Names
	IUPAC name (2Z)-2-benzylideneheptanal
	Other names alpha-Amyl cinnamaldehyde; alpha-Pentylcinnamaldehyde; Jasmonal
Identifiers
CAS Number	101365-33-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:32318;
ChEMBL	ChEMBL1611291;
ChemSpider	1361549;
DrugBank	DB14175;
ECHA InfoCard	100.004.129
EC Number	204-541-5;
KEGG	C12288;
PubChem CID	1712058;
UNII	06T2G22P2C ;
CompTox Dashboard (EPA)	DTXSID8029157 ;
	InChI InChI=1S/C14H18O/c1-2-3-5-10-14(12-15)11-13-8-6-4-7-9-13/h4,6-9,11-12H,2-3,5,10H2,1H3/b14-11- Key: HMKKIXGYKWDQSV-KAMYIIQDSA-N;
	SMILES CCCCC/C(=C/C1=CC=CC=C1)/C=O;
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H317, H411
Precautionary statements	P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Jasminaldehyde (also known as jasmine aldehyde and α-pentylcinnamaldehyde) is a fine chemical used as an aroma compound in perfumes. It is responsible for jasmine's characteristic scent.

Synthesis

Jasminaldehyde used in industry is commonly derived not from jasmine essential oil, but ultimately from the castor bean plant. The process starts with ricinoleic acid, the principal constituent of castor oil. This compound undergoes cracking to undecylenic acid (used mainly to produce Nylon 11) and heptanal. The heptanal, once distilled, is then reacted with benzaldehyde in the presence of a basic catalyst (trans-aldol condensation) to give jasminaldehyde and water. The foul-smelling 2-pentylnon-2-enal is an unwanted byproduct that results from the self-condensation of heptanal.^[1]^[2] This process parallels the preparation hexyl cinnamaldehyde from octanal and benzaldehyde.

References

^ Heynderickx, Philippe M. (2019-08-05). "Activity Coefficients for Liquid Organic Reactions: Towards a Better Understanding of True Kinetics with the Synthesis of Jasmin Aldehyde as Showcase". International Journal of Molecular Sciences. 20 (15): 3819. doi:10.3390/ijms20153819. ISSN 1422-0067. PMC 6695740. PMID 31387255.
^ G. A. Burdock, Fenaroli’s Handbook of Flavor Ingredients, Fifth Edition, 2005, CRC Press, Boca Raton, Fl., ISBN 0-8493-3034-3

[Heynde-1] Heynderickx, Philippe M. (2019-08-05). "Activity Coefficients for Liquid Organic Reactions: Towards a Better Understanding of True Kinetics with the Synthesis of Jasmin Aldehyde as Showcase". International Journal of Molecular Sciences. 20 (15): 3819. doi:10.3390/ijms20153819. ISSN 1422-0067. PMC 6695740. PMID 31387255.

[Fenaroli's-2] G. A. Burdock, Fenaroli’s Handbook of Flavor Ingredients, Fifth Edition, 2005, CRC Press, Boca Raton, Fl., ISBN 0-8493-3034-3

[1]

[2]