Jasminaldehyde (also known as jasmine aldehyde and α-pentylcinnamaldehyde) is a

fine chemical In chemistry, fine chemicals are complex, single, pure chemical substances, produced in limited quantities in multipurpose plants by multistep batch chemical or biotechnological processes. They are described by exacting specifications, used f ...

used as an

aroma compound An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...

perfume Perfume (, ) is a mixture of fragrance, fragrant essential oils or aroma compounds (fragrances), Fixative (perfumery), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agre ...

s. It is responsible for

jasmine Jasmine (botanical name: ''Jasminum'', pronounced ) is a genus of shrubs and vines in the olive family of Oleaceae. It contains around 200 species native to tropical and warm temperate regions of Eurasia, Africa, and Oceania. Jasmines are wid ...

's characteristic scent.

Synthesis

Jasminaldehyde used in industry is commonly derived not from jasmine essential oil, but ultimately from the

castor bean ''Ricinus communis'', the castor bean or castor oil plant, is a species of perennial flowering plant in the spurge family, Euphorbiaceae. It is the sole species in the monotypic genus, ''Ricinus'', and subtribe, Ricininae. The evolution of ca ...

plant. The process starts with

ricinoleic acid Ricinoleic acid, formally called 12-hydroxy-9-''cis''-octadecenoic acid, is a fatty acid. It is an Unsaturated fatty acid, unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from the seeds of casto ...

, the principal constituent of

castor oil Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its den ...

. This compound undergoes

cracking Cracking may refer to: * Cracking, the formation of a fracture or partial fracture in a solid material studied as fracture mechanics ** Performing a sternotomy * Fluid catalytic cracking, a catalytic process widely used in oil refineries for crac ...

undecylenic acid Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the s ...

(used mainly to produce

Nylon 11 Nylon 11 or Polyamide 11 (PA 11) is a polyamide, bioplastic and a member of the nylon family of polymers produced by the polymerization of 11-Aminoundecanoic acid, 11-aminoundecanoic acid. It is produced from castor beans by Arkema under the trad ...

) and

heptanal Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants. Production The formation of heptanal in the fractional distillation of cas ...

. The heptanal, once distilled, is then reacted with

benzaldehyde Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful. It is a colorless liquid with a characteristic almond-li ...

in the presence of a basic catalyst (''trans''-

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...

) to give jasminaldehyde and water. The foul-smelling 2-pentylnon-2-enal is an unwanted byproduct that results from the self-condensation of heptanal.G. A. Burdock, ''Fenaroli’s Handbook of Flavor Ingredients, Fifth Edition'', 2005, CRC Press, Boca Raton, Fl., This process parallels the preparation hexyl cinnamaldehyde from

octanal Octanal is the organic compound, an aldehyde, with the chemical formula CH3(CH2)6CHO. A colorless fragrant liquid with a fruit-like odor, it occurs naturally in citrus oils. It is used commercially as a component in perfumes and in flavor produ ...

and benzaldehyde. : Jasminaldehyd 2 IS

References

{{reflist Aldehydes Perfume ingredients