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

Celery ketone, also known as 3-Methyl-5-propyl-2-cyclohexen-1-one, is an organic compound with a warm, spicy, woody odor and a similar flavor at low levels. It can be synthesized through various methods, such as 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 an ethanol solution.

Uses

Used in Flavor and Fragrance Industry:
Celery ketone is used as a flavoring agent for its warm, spicy, and woody notes, adding depth and complexity to various food products and beverages.
Used in Perfumery:
Celery ketone is used as a fragrance ingredient in perfumes and colognes, providing a unique and distinctive scent that can enhance the overall aroma profile of the product.
Used in Cosmetics:
Celery ketone can be used in cosmetics as a natural alternative to synthetic fragrances, offering a pleasant and natural scent to skincare and beauty products.
Used in Pharmaceutical Industry:
Celery ketone may have potential applications in the pharmaceutical industry, such as in the development of drugs targeting specific receptors or enzymes, due to its unique chemical structure and properties. Further research is needed to explore these possibilities.

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 
• 570-08-1 diethyl acetylmalonate 
• 67-64-1 acetone 
• 3844-94-8 1-(trimethylsilyl)-1-hexyne 
• 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 
• 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 
• 779349-09-6 trimethyl-(2-methylene-4-propyl-hex-5-ynyl)-silane 
• 765906-93-2 2-methyl-4-propyl-hex-1-en-5-yne 

Downstream Products

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

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.