553-84-4

Usage

Uses

Used in Culinary Industry:
Perilla ketone is used as a flavoring agent in oriental foods for its distinct taste and aroma, enhancing the overall dining experience. Despite its toxicity, it is utilized in controlled amounts to ensure safety while maintaining the desired flavor profile.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 4833, 1984 DOI: 10.1021/ja00329a032Tetrahedron Letters, 33, p. 5245, 1992 DOI: 10.1016/S0040-4039(00)79145-3

Safety Profile

Poison by intravenous and intraperitoneal routes. A potent pulmonary edemagenic agent (experimental). May also be hazardous to humans. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes

InChI:InChI=1/C10H14O2/c1-8(2)3-4-10(11)9-5-6-12-7-9/h5-8H,3-4H2,1-2H3

Synthetic route

furan-3-carbonyl chloride (26214-65-3) + isopentylmanganese chloride → Perillaketone (553-84-4)

Conditions	Yield
With copper(l) chloride In tetrahydrofuran -10 deg C to r.t., then 20 min;	94%

4-methylvaleroyl chloride (38136-29-7) + tributyl(furan-3-yl)stannane (87453-06-3) → Perillaketone (553-84-4)

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 12h; Ambient temperature;	74%

furan-3-carbonyl chloride (26214-65-3) + diisopentyl cadmium (35061-27-9) → Perillaketone (553-84-4)

Conditions	Yield
With benzene

(furan-3-carbonyl)-isobutyl-malonic acid diethyl ester → Perillaketone (553-84-4)

Conditions	Yield
With sulfuric acid; acetic acid

4-methylvaleroyl chloride (38136-29-7) + 3-furyllithium (53101-93-2) → Perillaketone (553-84-4)

Conditions	Yield
With manganese chloride bis(lithium chloride); iron(III)-acetylacetonate 1) THF, -80 deg C, 30 min, 2) -70 deg C, 30 min; Yield given. Multistep reaction;

Dichloromethyl methyl ether (4885-02-3) + (3-furyl)(3-methylbutyl)(isopropoxy)borane (109529-24-0) → Perillaketone (553-84-4)

Conditions	Yield
With dihydrogen peroxide; lithium tert-butoxide 1.) diethyl ether, r.t., 1 h, 2.) diethyl ether, pH 8 phosphate buffer, 12 h; Yield given. Multistep reaction;

1-(1-Ethoxy-1-furan-3-yl-4-methyl-pentyl)-1H-benzotriazole (1025878-40-3) → Perillaketone (553-84-4)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature; Yield given;

furan-3-carboxaldehyde (498-60-2) → Perillaketone (553-84-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / H2SO4 / ethanol; tetrahydrofuran / 3 h / Ambient temperature 2: n-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 2.) -78 deg C, 2 min 3: aq. HCl / tetrahydrofuran / Ambient temperature View Scheme

3-<(Benzotriazol-1-yl)ethoxymethyl>furan (172265-13-3) → Perillaketone (553-84-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 2.) -78 deg C, 2 min 2: aq. HCl / tetrahydrofuran / Ambient temperature View Scheme

i-pentyl bromide (107-82-4) → Perillaketone (553-84-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 2.) -78 deg C, 2 min 2: aq. HCl / tetrahydrofuran / Ambient temperature View Scheme

Perillaketone (553-84-4) → 3-Isohexyl-furan (873974-68-6)

Conditions	Yield
With hydrogenchloride; amalgamated zinc

Perillaketone (553-84-4) → 3-Isohexyl-tetrahydro-furan

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc-amalgam; aqueous hydrochloric acid 2: palladium; acetic acid / Hydrogenation View Scheme

Upstream product

• 26214-65-3 furan-3-carbonyl chloride 
• 35061-27-9 diisopentyl cadmium 
• 38136-29-7 4-methylvaleroyl chloride 
• 53101-93-2 3-furyllithium 
• 87453-06-3 tributyl(furan-3-yl)stannane 
• 498-60-2 furan-3-carboxaldehyde 
• 107-82-4 i-pentyl bromide 
• 172265-13-3 3-<(Benzotriazol-1-yl)ethoxymethyl>furan 
• 1025878-40-3 1-(1-Ethoxy-1-furan-3-yl-4-methyl-pentyl)-1H-benzotriazole 
• 4885-02-3 Dichloromethyl methyl ether 
• 109529-24-0 (3-furyl)(3-methylbutyl)(isopropoxy)borane 

Relevant academic research and scientific papers

Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones

Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding α-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield.The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation.Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), α-hydroxyalkyl (12 and 13), α-aminoalkyl (14) and acyl (15) substituents.

A new simple route to furanic ketones; preparation of elsholtzione naginata ketone and perilla ketone

Copper- or iron-catalyzed acylation of organomanganese reagents allows to obtain 3- and 2-acylfurans in high yields. Elsholtzione, naginata ketone and perilla ketone have been prepared according to this procedure.

A mild, efficient approach to 3-acylfurans: A short synthesis of perilla ketone

Several 3-acylfurans 3 were prepared in excellent yield using a one-pot procedure involving the palladium-catalyzed cross-coupling of commercially available acid chlorides with tributyl(3-furyl)-stannane 2 at room temperature.