54947-74-9

Basic information

• Product Name: 4-Methyloctanoic acid
• Synonyms: (R,S)-(+/-)-4-METHYLOCTANOIC ACID;4-methyl-octanoicaci;Octanoic acid, 4-methyl-;4-METHYLCAPRYLIC ACID;(+/-)-4-METHYLOCTANOIC ACID;4-METHYLOCTANOIC ACID;FEMA 3575;FEMA NUMBER 3575
• CAS NO: 54947-74-9
• Molecular Formula: C₉H₁₈O₂
• Molecular Weight: 158.24
• EINECS: 259-404-2
• Product Categories: API intermediates;acid Flavor;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 54947-74-9.mol

Chemical Properties

• Melting Point: -29.5°C (estimate)
• Boiling Point: 149 °C22 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: COA
• Density: 0.91 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0057mmHg at 25°C
• Refractive Index: n20/D 1.433(lit.)
• Storage Temp.: −20°C
• PKA: 4.78±0.10(Predicted)
• BRN: 1755426
• CAS DataBase Reference: 4-Methyloctanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyloctanoic acid(54947-74-9)
• EPA Substance Registry System: 4-Methyloctanoic acid(54947-74-9)

Safety Data

• Hazard Codes: C,Xi,Xn
• Statements: 34-36/37/38-21/22
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 54947-74-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
4-Methyloctanoic acid is used as a flavoring agent for various food products, particularly cheese, meat, and tobacco, due to its characteristic fatty, waxy, creamy, and lactonic taste with a satiating fatty mouthfeel and metallic nuances. It is also used in flavors for fish.
Used in Fragrance Industry:
4-Methyloctanoic acid is used as a fragrance ingredient in the perfumery industry, where it contributes to the waxy, fatty, meaty, and slightly lactonic cheesy aroma.
Used in Cheese Flavoring:
4-Methyloctanoic acid is used as a flavoring agent in cheese, providing a sweaty and goaty flavor to goat's milk cheese.
Used in Meat Flavoring:
4-Methyloctanoic acid is used as a flavoring agent in the meat industry, particularly for mutton, to enhance its characteristic sweaty and goaty flavor.
Used in Tobacco Flavoring:
4-Methyloctanoic acid is used as a flavoring agent in the tobacco industry, where it contributes to the overall flavor profile of the product.
Normal use levels in finished consumer products for 4-Methyloctanoic acid are up to 3 ppm. It is reported to be found in cooked mutton fat, raw and cooked mutton, lamb, and various types of cheese, such as blue, cheddar, parmesan, provolone, and romano.

Biochem/physiol Actions

Taste at 10 ppm

InChI:InChI=1/C9H18O2/c1-3-4-5-8(2)6-7-9(10)11/h8H,3-7H2,1-2H3,(H,10,11)/p-1/t8-/m0/s1

Upstream product

• 171627-79-5 (4R)-Methyloctanol 
• 124-38-9 carbon dioxide 
• 64-17-5 ethanol 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 41144-01-8 (S)-3,7-dimethyl-6-octenyl tosylate 
• 7758-89-6 copper(I) chloride 
• 925-90-6 ethylmagnesium bromide 
• 171627-77-3 (6R)-2,6-Dimethyl-2-decene 
• 138851-11-3 (4R)-4-methyl-1-octanol 
• 4316-44-3 4-oxooctanoic acid 
• 10340-84-8 (S)-citronellyl bromide 
• 63037-60-5 diethyl 2-methylhexylmalonate 
• 50876-10-3 5-ethyl-2-thiophthenecarboxylic acid 
• 214126-59-7 2,6-dimethyl-2-decene 

Downstream Products

• 16177-10-9 (R)-4-methyloctanoic acid ethyl ester 
• 313653-37-1 (4R,5S)-4-methyl-3-((R)-4-methyl-octanoyl)-5-phenyl-oxazolidin-2-one 
• 313653-38-2 (3S,5R)-5-Methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-nonanoic Acid Tert-butyl Ester 
• 56196-53-3 (+/-)-Ethyl 4-methyloctanoate 
• 53696-14-3 6-methyldecanoic acid 
• 38514-03-3 4-methyloctan-1-ol 
• 54947-74-9 (4R)-4-Methyloctanoic acid 
• 128342-72-3 (4S)-4-methyloctanoic acid 
• 54831-51-5 (S)-4-methyloctanoic acid ethyl ester 

Relevant articles and documents

Pheromone synthesis. Part 258. Synthesis of the enantiomers of the beetle pheromones ethyl 4-methylheptanoate, 4-methyloctanoic acid and 4-methyl-1-nonanol, and HPLC analysis of their derivatives to determine their enantiomeric purities

The enantiomers of citronellal have been converted into the enantiomers of the following beetle pheromones: ethyl 4-methylheptanoate (produced by male Nicrophorus vespilloides), 4-methyloctanoic acid (produced by male Oryctes elegans), and 4-methyl-1-nonanol (produced by female Tenebrio molitor). The enantiomeric purities of the synthetic pheromones were determined by HPLC analysis of the corresponding acids after derivatization with Ohrui's reagent [(S)-1-(anthracene-2,3-dicarboximido)-2-propanol]. The enantiomers of 4-methyl-1-nonanol could also be analyzed employing another Ohrui's reagent [(1S,2S)-2-(naphthalene-2,3-dicarboximido)cyclohexane-1-carboxylic acid].

New synthesis of vanillin by degradation of lignin in presence of functional basic ionic liquid

The degradation of lignin catalyzed by functional basic ionic liquid was investigated. Higher conversion of lignin and simpler degradation product composition were obtained in the presence of basic ionic liquid, comparing with that under traditional NaOH

Method for Producing Isononanoic Acid Esters, Starting from 2-Ethyl Hexanol

A Process for preparing carboxylic esters of a mixture of structurally branched C9 monocarboxylic acids proceeding from 2-ethylhexanol is characterized in that (a) 2-ethylhexanol is dehydrated to an octene mixture in the presence of a catalyst; (b) the octene mixture obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give a mixture of isomeric isononanals; (c) the mixture of isomeric isononanals obtained in step b) is oxidized to a mixture of structurally branched C9 monocarboxylic acids; and (d) the mixture of structurally branched C9 monocarboxylic acids obtained in step c) is reacted with alcohols to give carboxylic esters.

Method for Producing Isononanoic Acids from 2-Ethyl Hexanol

Process for preparing isononanoic acid proceeding from 2-ethylhexanol, characterized in that (a) 2-ethylhexanol is dehydrated to octene in the presence of a catalyst; (b) the octene obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give isononanal; and (c) the isononanal obtained in step b) is oxidized to isononanoic acid.

Carboxy-directed asymmetric hydrogenation of 1,1-diarylethenes and 1,1-dialkylethenes

Carboxy marks the spot: A carboxy-directed asymmetric hydrogenation of 1,1-diarylethenes and 1,1-dialkylethenes with chiral iridium/spiro phosphine-oxazoline catalysts has been developed. A wide range of chiral diarylethanes and chiral γ-methyl fatty acids were synthesized with excellent enantioselectivity (see scheme). Copyright

Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters

The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on

Diastereoselective, large-scale synthesis of β-amino acids via asymmetric aza-Michael addition as α2δ ligands for the treatment of generalized anxiety disorder and insomnia

Scalable synthetic routes to β-amino acids 1 and 2 are presented. These two compounds, which bind to the α2δ subunit of calcium channels and have important medical applications, have been prepared on kilogram scale in our pilot plant through an improved synthesis that avoids the use of highly toxic reagents and hazardous chemistry present in the original Medicinal Chemistry route. The two chiral centers are introduced through asymmetric Michael and aza-Michael reactions with excellent diastereoselectivity.

Efficient synthesis of (±)-4-methyloctanoic acid, aggregation pheromone of rhinoceros beetles of the genus oryctes (Coleoptera: Dynastidae, Scarabaeidae)

(±)-4-Methyloctanoic acid and its ethyl ester are aggregation pheromones of many rhinoceros beetles of the genus Oryctes and are investigated for the control of these pests by olfactory trapping. A simple, economical, and high-yield (>50%) synthesis of (±)-4-methyloctanoic acid and its ethyl ester is presented starting from n-hexanal. The key step in this sequence is an orthoester Claisen rearrangement for the elongation of the carbon chain by two.

METHODS FOR USING AMINO ACIDS WITH AFFINITY FOR THE ALPHA-2-DELTA PROTEIN

This invention relates to certain ?-amino acids that bind to the alpha-2-delta ((x2S) subunit of a calcium channel. These compounds and their pharmaceutically acceptable salts are useful in the treatment of a variety of psychiatric, pain and other disorders.