496-77-5

Basic information

• Product Name: 5-Hydroxy-4-octanone
• Synonyms: 4-Octanone, 5-hydroxy-;5-hydroxy-4-octanon;5-Octanol-4-one;FEMA 2587;BUTYROIN;5-HYDROXY-4-OCTANONE;TIMTEC-BB SBB008396;5-hydroxyoctan-4-one
• CAS NO: 496-77-5
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21
• EINECS: 207-830-4
• Product Categories: ketone Flavor;Alphabetical Listings;Flavors and Fragrances;G-H
• Mol File: 496-77-5.mol
• Article Data: 26

Chemical Properties

• Melting Point: -10°C
• Boiling Point: 80-82 °C10 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: /
• Density: 0.916 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.172mmHg at 25°C
• Refractive Index: n20/D 1.4315(lit.)
• PKA: 13.13±0.20(Predicted)
• Merck: 14,1595
• CAS DataBase Reference: 5-Hydroxy-4-octanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-4-octanone(496-77-5)
• EPA Substance Registry System: 5-Hydroxy-4-octanone(496-77-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 496-77-5(Hazardous Substances Data)

Usage

Description

5-Hydroxy-4-octanone is an organic compound characterized by its sweet, slightly pungent, buttery, nutlike odor and a sweet, buttery, oily taste. It can be synthesized by reacting sodium metal with ethyl butyrate in boiling ether or starting from methyl butyrate.

Uses

Used in Flavor Industry:
5-Hydroxy-4-octanone is used as a flavoring agent for its distinctive sweet, buttery, and nutty taste and aroma. It is particularly useful in the creation of artificial flavors for the food and beverage industry, where it can enhance the taste and smell of various products.
Used in Fragrance Industry:
5-Hydroxy-4-octanone is used as a fragrance ingredient for its sweet, slightly pungent, and buttery scent. It can be incorporated into perfumes, colognes, and other scented products to provide a rich, complex, and pleasant aroma.
Used in Chemical Synthesis:
5-Hydroxy-4-octanone can be used as a starting material or intermediate in the synthesis of various chemicals and compounds. Its unique chemical properties make it a valuable building block for creating new molecules with specific applications in different industries.
Used in Research and Development:
5-Hydroxy-4-octanone is utilized in research and development for studying its chemical properties, reactions, and potential applications in various fields. Scientists and researchers can use this compound to explore new methods of synthesis, investigate its interactions with other molecules, and develop novel applications in various industries.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 5-Hydroxy-4-octanone may have potential applications in the pharmaceutical industry due to its unique chemical properties. It could be used as a building block for the development of new drugs or as an intermediate in the synthesis of pharmaceutical compounds. Further research and development would be required to explore these possibilities.

Preparation

By reacting sodium metal with ethyl butyrate in boiling ether or in the same fashion starting from methyl butyrate.

InChI:InChI=1/C8H16O2/c1-3-5-7(9)8(10)6-4-2/h7,9H,3-6H2,1-2H3/t7-/m1/s1

Upstream product

• 623-42-7 butanoic acid methyl ester 
• 141-75-3 butyryl chloride 
• 6802-75-1 diethyl isopropylidenemalonate 
• 123-72-8 butyraldehyde 
• 17085-88-0 diethyl propylidenemalonate 
• 50265-96-8 N-tert-butyl-N'-butylidenehydrazine 
• 623-70-1 ethyl (E)-crotonate 
• 624-49-7 dimethylfumarate 
• 5455-24-3 octane-4,5-dione 
• 86348-26-7 4,5-bis-butyryloxy-oct-4-ene 
• 105-54-4 butanoic acid ethyl ester 
• 2432-51-1 ethylthioacetic acid methyl ester 
• 140-88-5 ethyl acrylate 
• 927-77-5 n-propylmagnesium bromide 

Downstream Products

• 101256-06-8 5-benzylcarbamoyloxy-octan-4-one 
• 101355-91-3 5-benzylamino-octan-4-one 
• 82998-35-4 2-(4-methoxyphenyl)-5-propyl-4-propylidene-1,3,2-oxathiaphosphole 2-sulfide 
• 74550-96-2 2-Guanidino-4,5-dipropyl-oxazol-hydrochlorid 
• 59417-50-4 2,3-dipropyl-quinoxaline 
• 1684-14-6 2,3-diphenylquinoxaline 
• 589-62-8 octan-4-ol 
• 1942-45-6 4-Octyne 
• 1449280-47-0 2-[[2-(benzyloxycarbonylamino)acetyl]amino]-6-(1,3-dimethyl-4,5-dipropyl-imidazol-1-ium-2-yl)sulfanyl-5-oxo-hexanoic acid bromide 
• 1449280-46-9 2-[[2-(benzyloxycarbonylamino)-3-phenyl-propanoyl]amino]-6-(1,3-dimethyl-4,5-dipropyl-imidazol-1-ium-2-yl)sulfanyl-5-oxo-hexanoic acid bromide 
• 1021305-94-1 C₁₆H₂₄O₃ 
• 108985-24-6 3-benzyl-4,5-dipropyl-3H-oxazol-2-one 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 589-63-9 octan-4-one 

Relevant articles and documents

Sol-gel synthesis of ceria-zirconia-based high-entropy oxides as high-promotion catalysts for the synthesis of 1,2-diketones from aldehyde

Efficient Lewis-acid-catalyzed direct conversion of aldehydes to 1,2-diketones in the liquid phase was enabled by using newly designed and developed ceria–zirconia-based high-entropy oxides (HEOs) as the actual catalysts. The synergistic effect of various cations incorporated in the same oxide structure (framework) was partially responsible for the efficiency of multicationic materials compared to the corresponding single-cation oxide forms. Furthermore, a clear, linear relationship between the Lewis acidity and the catalytic activity of the HEOs was observed. Due to the developed strategy, exclusively diketone-selective, recyclable, versatile heterogeneous catalytic transformation of aldehydes can be realized under mild reaction conditions.

Tandem hydroformylation/acyloin reaction - The synergy of metal catalysis and organocatalysis yielding acyloins directly from olefins

A novel, atom efficient, orthogonal tandem catalysis was developed yielding acyloin products (α-hydroxy ketones) directly from olefins under hydroformylation conditions. The combination of a metal-catalysed hydroformylation and an organocatalysed acyloin reaction provides three atom efficient C-C bond formations to linear, multifunctional molecules via linkage of the intermediate n-aldehydes. Additionally, the rhodium catalyst system gives a high n/bra ratio with an exclusive conversion of the terminal double bond in the hydroformylation and the n-aldehydes are converted selectively to their acyloins.

Polyether-substituted thiazolium ionic liquid catalysts - A thermoregulated phase-separable catalysis system for the Stetter reaction

A series of polyether-substituted thiazolium ionic liquids have been synthesized and used as catalysts in the Stetter reaction. The ionic liquids are a thermoregulated phase-separable catalysis (TPSC) system, because they possess the properties of critical solution temperature (CST) and inverse temperature-dependent solubility in toluene-heptane. The results showed that the novel TPSC system exhibits high recycling efficiency, and provides a potential route for a environmentally benign Stetter reaction. The Royal Society of Chemistry 2010.