2412-80-8

Basic information

• Product Name: FEMA 2721
• Synonyms: PENTANOIC ACID, 4-METHYL-, METHYL ESTER;FEMA NUMBER 2721;FEMA 2721;METHYL ISOCAPROATE;METHYL 4-METHYLVALERATE;METHYL 4-METHYLPENTANOATE;4-methyl-pentanoicacimethylester;4-Methylvaleric acid, methyl ester
• CAS NO: 2412-80-8
• Molecular Formula: C₇H₁₄O₂
• Molecular Weight: 130.18
• EINECS: 219-320-9
• Mol File: 2412-80-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 139-140 °C(lit.)
• Flash Point: 103 °F
• Appearance: /Liquid
• Density: 0.888 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.85mmHg at 25°C
• Refractive Index: n20/D 1.404(lit.)
• CAS DataBase Reference: FEMA 2721(CAS DataBase Reference)
• NIST Chemistry Reference: FEMA 2721(2412-80-8)
• EPA Substance Registry System: FEMA 2721(2412-80-8)

Safety Data

• Statements: 10
• Safety Statements: 16-27-36/37/39
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 2412-80-8(Hazardous Substances Data)

Usage

Description

Methyl 4-methylvalerate has a sweet, pineapple-like flavor. Prepared from isocapric acid and methanol at the boil in the presence of H2S04.

Chemical Properties

Methyl-4-methylvalerate has a sweet, pineapple-like flavor

Occurrence

Reported found in pineapple and strawberry

Preparation

From isocapric acid and methanol at the boil in the presence of H2SO4

Taste threshold values

Taste characteristics at 50 ppm: fruity, sweet, banana, pineapple, apple-like with ripe, candy nuances.

InChI:InChI=1/C7H14O2/c1-6(2)4-5-7(8)9-3/h6H,4-5H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 646-07-1 4-Methylpentanoic acid 
• 75-28-5 Isobutane 
• 6832-16-2 methyl diazoacetate 
• 513-35-9 2-methyl-but-2-ene 
• 201230-82-2 carbon monoxide 
• 504-60-9 penta-1,3-diene 
• 38136-29-7 4-methylvaleroyl chloride 
• 1160845-87-3 C₇H₁₄N₂O₂ 
• 83594-04-1 4-methylpentanoic anhydride 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 35070-57-6 isopentylmercury ⁽¹⁺⁾; bromide 
• 75917-29-2 2-propylazodiphenylmethanol 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 626-88-0 1-bromo-5-methylpentane 
• 1647153-61-4 (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester 
• 140157-44-4 4-methylpentanehydrazide 
• 186602-92-6 4-Methyl-2-(2-tritylsulfanyl-acetyl)-pentanoic acid methyl ester 
• 626-89-1 4-Methyl-1-pentanol 

Relevant articles and documents

Iron-catalysed 1,2-aryl migration of tertiary azides

1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.

Three step auto-tandem catalysed hydroesterification: Access to linear fruity esters from piperylene

A convenient and selective access to saturated hexanoic esters via hydroesterification of piperylene with synthesis gas and methanol is presented. This is the first three step auto-tandem hydroesterification, which is 100% atom economic proceeding under mild conditions. Our optimisations revealed Pd2(dba)3/1,2-dtbpmb as the best catalytic system. Besides, the reaction also tolerates several alcohols, which offers a broad range of fruity esters. In addition, we present insights into the reaction sequence, investigating whether the reaction proceeds via two- or three-step reaction cascade.

Amino acid motifs in natural products: Synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

(2S,3S)-3-Hydroxyleucine can be found in an increasing number of bioactive natural products. Within the context of our work regarding the total synthesis of muraymycin nucleoside antibiotics, we have developed a synthetic approach towards (2S,3S)-3- hydroxyleucine building blocks. Application of different protecting group patterns led to building blocks suitable for C- or N-terminal derivatization as well as for solid-phase peptide synthesis. With respect to according motifs occurring in natural products, we have converted these building blocks into 3-O-acylated structures. Utilizing an esterification and cross-metathesis protocol, (2S,3S)-3-hydroxyleucine derivatives were synthesized, thus opening up an excellent approach for the synthesis of bioactive natural products and derivatives thereof for structure activity relationship (SAR) studies.