3720-16-9

Basic information

• Product Name: Celery ketone
• Synonyms: 3-methyl-5-propylcyclohex-2-enone;CELERY KETONE;FEMA 3357;FEMA 3577;Livescone;2-Cyclohexen-1-one, 3-methyl-5-propyl-;3-METHYL-5-PROPYLCYCLOHEX-2-EN-1-ONE(CELERYKETONE);3-Methyl-5-propylcyclohex-2-enon
• CAS NO: 3720-16-9
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 223-069-0
• Product Categories: ketone Flavor
• Mol File: 3720-16-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 231.339 °C at 760 mmHg
• Flash Point: 94.621 °C
• Appearance: /
• Density: 0.904 g/cm³
• Vapor Pressure: 0.0627mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: Celery ketone(CAS DataBase Reference)
• NIST Chemistry Reference: Celery ketone(3720-16-9)
• EPA Substance Registry System: Celery ketone(3720-16-9)

Safety Data

• Hazardous Substances Data: 3720-16-9(Hazardous Substances Data)

Usage

Description

3-Methyl-5-propyl-2-cyclohexen-l-one has a warm, spicy, woody odor with a similar flavor at low levels. May be prepared by condensation of butyric aldehyde with ethyl acetoacetate in the presence of diethylamine and subsequent saponification with a 10% KOH solution; or by condensation in the presence of piperidine in ethanol solution.

Chemical Properties

3-Methyl-5-propyl-2-cyclohexen-1-one has a warm, spicy, woody odor

Preparation

By condensation of butyric aldehyde with ethyl acetoacetate in the presence of diethylamine and subsequent saponification with a 10% KOH solution, or by condensation in the presence of piperdine in ethanol solution

InChI:InChI=1/C10H16O/c1-3-4-9-5-8(2)6-10(11)7-9/h6,9H,3-5,7H2,1-2H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 123-72-8 butyraldehyde 
• 67-64-1 acetone 
• 3844-94-8 1-(trimethylsilyl)-1-hexyne 
• 765906-93-2 2-methyl-4-propyl-hex-1-en-5-yne 
• 765906-73-8 4-propyl-6-triisopropylsilanyloxy-2-trimethylsilanylmethyl-hex-1-en-5-yne 
• 765906-69-2 triisopropyl-(5-methyl-3-propyl-hex-5-en-1-ynyloxy)-silane 
• 5609-09-6 3-hepten-2-one 
• 95557-23-6 4-Hydroxy-6-oxo-4-methyl-2-propyl-cyclohexan-dicarbonsaeure-(1,3)-di-tert-butylester 
• 541-47-9 3-Methylbutenoic acid 
• 13419-69-7 (E)-2-Hexenoic acid 
• 570-08-1 diethyl acetylmalonate 
• 779349-09-6 trimethyl-(2-methylene-4-propyl-hex-5-ynyl)-silane 

Downstream Products

• 91250-80-5 1,3-Dimethyl-5-propyl-cyclohexadien-(1,3) 
• 36186-96-6 3-Methyl-5-propyl-phenol 
• 855428-06-7 1-methyl-3-oxo-5-propyl-cyclohexanecarbonitrile 
• 97908-74-2 methyl E-3-methyl-5-propylcyclohexylidene acetate 
• 97908-74-2 methyl Z-3-methyl-5-propylcyclohexylidene acetate 
• 856352-04-0 6-Hydroxy-1.4-dimethyl-2-propyl-benzol 
• 67662-98-0 3-methyl-5-propylcyclohexanone 

Relevant articles and documents

The synthesis of cyclohexenone using l-proline immobilized on a silica gel catalyst by a continuous-flow approach

A facile and convenient method for the synthesis of cyclohexenone compounds was developed using an l-proline immobilized silica gel catalyst combined with a continuous-flow approach. Because of the mild reaction conditions, ease of catalyst recyclability, and product isolation, this reaction approach can potentially be used in a facile scale-up reaction or in industrial applications. the Partner Organisations 2014.

An efficient synthesis of some 5-substituted-3-methyl-2-cyclohexen-1-ones using microwaves

3-Methyl-2-cyclohexenone and its 5-substituted-derivatives are prepared in high yields and short duration of time, using the microwave irradiation technique by the condensation of ethyl acetoacetate with eight different aldehydes and piperazine.

Br?nsted acid-promoted cyclizations of siloxy alkynes with unactivated arenes, alkenes, and alkynes

In this article, we describe the development of a general concept for the development of new carbon-carbon bond-forming processes, which is based on Br?nsted acid-mediated activation of a siloxy alkyne, followed by efficient interception of the resulting highly reactive ketenium ion by unactivated arenes, alkenes or alkynes. We found that trifluoromethane sulfonimide (HNTf2) proved to be a superior promoter of these reactions compared to a range of other Br?nsted acids. This finding could be attributed to a high acidity of HNTf2 in aprotic organic solvents combined with a low nucleophilicity of the NTf2- anion. Depending on the nature of the nucleophile, the carbocyclizations proceeded either via 6-endo-dig or 5-endo-dig manifolds. In the case of 1-siloxy-1,5-diynes, the cyclizations occurred with a concomitant halide abstraction or arylation.