106-73-0

Basic information

• Product Name: Methyl heptanoate
• Synonyms: METHYL HEPTANOATE 99+%;METHYL HEPTANOATE 99+% NATURAL;METHYL ENANTHATE OEKANAL;METHYL HEPTANOATE, STANDARD FOR GC;METHYLHEPTANOATE(SG);ENANTHIC ACID METHYL ESTER: 99.5%;Methyl Heptanoate [Standard Material];METHYL HEPTOATE, NATURAL
• CAS NO: 106-73-0
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21
• EINECS: 203-428-8
• Product Categories: Analytical Chemistry;Fatty Acid Methyl Esters (GC Standard);Standard Materials for GC
• Mol File: 106-73-0.mol

Chemical Properties

• Melting Point: -56°C
• Boiling Point: 172-173 °C(lit.)
• Flash Point: 127 °F
• Appearance: /Liquid
• Density: 0.87 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.43mmHg at 25°C
• Refractive Index: n20/D 1.411(lit.)
• Storage Temp.: Store below +30°C.
• BRN: 1747147
• CAS DataBase Reference: Methyl heptanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl heptanoate(106-73-0)
• EPA Substance Registry System: Methyl heptanoate(106-73-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 2
• RTECS: MJ2297500
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 106-73-0(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Methyl heptanoate is used as a flavor and fragrance compound for its sweet fruity and green taste characteristics at 35 ppm. It is commonly found in the aroma of fruits such as pineapple, papaya, blackberry, strawberry, and starfruit, as well as in vegetables like peas and pepper.
Used in Food Industry:
Methyl heptanoate is used as an additive in the food industry to enhance the flavor and aroma of various products, including Parmesan cheese, hop oil, white wine, and olive oil.
Used in Gas Chromatography:
Methyl heptanoate may be used as an external standard for the extraction and quantification of aroma compounds in complex matrices using gas chromatography technique.
Used in Chemical Synthesis:
Methyl heptanoate can be used as a starting material or intermediate in the synthesis of various chemicals and pharmaceuticals.
Occurrence:
Methyl heptanoate has been reported to be found in a wide range of natural sources, including cranberry, papaya, pineapple, blackberry, strawberry, peas, pepper, Parmesan cheese, hop oil, white wine, olive, starfruit, malt, Bourbon vanilla, mountain papaya, endive, nectarine, lamb's lettuce, mussel, spineless monkey orange, and rooibos tea (Aspalathus linearis).

Preparation

By treating heptanoic acid with methyl alcohol in the presence of HCl or H2SO4

Synthesis Reference(s)

Canadian Journal of Chemistry, 52, p. 3651, 1974 DOI: 10.1139/v74-546Journal of the American Chemical Society, 95, p. 1296, 1973 DOI: 10.1021/ja00785a047Tetrahedron Letters, 29, p. 3833, 1988 DOI: 10.1016/S0040-4039(00)82127-9

InChI:InChI=1/C8H16O2/c1-3-4-5-6-7-8(9)10-2/h3-7H2,1-2H3

Upstream product

• 6832-16-2 methyl diazoacetate 
• 109-66-0 pentane 
• 67-56-1 methanol 
• 628-71-7 1-Heptyne 
• 111-14-8 oenanthic acid 
• 592-41-6 1-hexene 
• 107-31-3 Methyl formate 
• 74-85-1 ethene 
• 177-10-6 1,3-dioxolane-2-spirocyclohexane 
• 712-74-3 1,2,4,5-tetracyanobenzene 
• 15719-55-8 trimethyl(oct-1-yn-1-yl)silane 
• 111-71-7 heptanal 
• 40416-74-8 1-Hydroperoxy-1-methoxypentan 
• 111-70-6 n-heptan1ol 

Downstream Products

• 5445-31-8 2-methyl-nonan-3-one 
• 624-16-8 decan-4-one 
• 54340-91-9 methyl rac-2-hydroxyheptanoate 
• 22371-32-0 heptanoic acid hydrazide 
• 6790-20-1 7-hydroxy-dodecan-6-one 
• 95633-74-2 2-heptanoyl-1-methyl-1H-imidazole 
• 111620-59-8 1,1-Bis-(1-methyl-1H-imidazol-2-yl)-heptan-1-ol 
• 2051-31-2 4-decanol 
• 111-70-6 n-heptan1ol 
• 16761-12-9 potassium salt of enanthic acid 
• 16761-13-0 Lithium n-heptanoate 
• 111-29-5 1 ,5-pentanediol 
• 110-63-4 Butane-1,4-diol 
• 40646-07-9 heptane-1,4-diol 

Relevant articles and documents

Ruthenium complex immobilized on supported ionic-liquid-phase (SILP) for alkoxycarbonylation of olefins with CO2

In this study, the heterogeneously catalyzed alkoxycarbonylation of olefins with CO2based on a supported ionic-liquid-phase (SILP) strategy is reported for the first time. An [Ru]@SILP catalyst was accessed by immobilization of ruthenium complex on a SILP, wherein imidazolium chloride was chemically integrated at the surface or in the channels of the silica gel support. An active Ru site was generated through reacting Ru3(CO)12with the decorated imidazolium chloride in a proper microenvironment. Different IL films, by varying the functionality of the side chain at the imidazolium cation, were found to strongly affect the porosity, active Ru sites, and CO2adsorption capacity of [Ru]@SILP, thereby considerably influencing its catalytic performance. The optimized [Ru]@SILP-A-2 displayed enhanced catalytic performance and prominent substrate selectivity compared to an independent homogeneous system under identical conditions. These findings provide the basis for a novel design concept for achieving both efficient and stable catalysts in the coupling of CO2with olefins.

Tuning the regioselectivity of (benzimidazolylmethyl)amine palladium(II) complexes in the methoxycarbonylation of hexenes and octenes

Reactions of N-(1H-benzoimidazol-2-ylmethyl-2-methoxy)aniline (L1) and N-(1H-benzoimidazol-2-ylmethyl-2-bromo)aniline (L2) with p-TsOH, Pd(AOc)2 and two equivalents of PPh3 or PCy3 produced the corresponding palladium comp

Efficient and selective oxidation of aldehydes with dioxygen catalysed by vanadium-containing heteropolyanions

The heteropolyacids “H3+n[PMo12–nVnO40]·aq” (denoted as HPA-n; n = 2, 3, 8) catalyse the oxidation of aldehydes to carboxylic acids in the presence of dioxygen with very good yields. The effect on the catalytic activity of various parameters such as the precursors, solvent, temperature or catalyst/substrate ratio was examined. The process is particularly selective for linear and aromatic aldehydes. The oxidation of adipaldehyde with dioxygen in mild conditions, in the presence of HPA-2 as a catalyst, leads to the formation of adipic acid together with a significant amount of other byproducts. Thus, several modifications of the catalytic systems have been carried out to improve their selectivity. The effect of cocatalysts was investigated and, among the species tested, complex Ni(acac)2 was found to be the most efficient yielding 60% of adipic acid.

VITAMIN B12 PHOTOELECTROCATALYSED (B12/PEC) SYNTHESIS OF 2-AMINOESTERS

Vit.B12 photoelectrocatalysed addition of alkyl bromides and carboxylic anhydrides to methyl 2-acetamidoacrylate yields 2-aminoesters.

Platinum Complex Catalyzed Carbonylation of Organic Iodides: Effective Carbonylation of Organic Iodides Having β-Hydrogens on Saturated sp3 Carbons

Dichlorobis(triphenylphosphine)platinum(II) is an effective catalyst precursor for the carbonylation of organic iodides having β-hydrogens on saturated sp3 carbons.The carbonylation under carbon monoxide pressure in the presence of alcohol gives esters, and aldehydes are obtained by the reaction under carbon monoxide and hydrogen pressure.Thus, 1-iodohexane is carbonylated to methyl heptanoate in 79percent yield in the presence of methanol at 120 deg C under 70 kg cm-2 of initial carbon monoxide pressure.Heptanal is formed in 86percent yield from 1-iodohexane at 120 deg Cunder carbon monoxide (50 kg cm-2) and hydrogen (50 kg cm-2).Alkenyl und alkynyl iodides are also smoothly carbonylated in the presence of alcohol into the corresponding esters without reduction of unsaturated bonds.

Isolation of the β-galactosphingolipid coniferoside using a tumor cell proteome reverse affinity protocol

New approaches are vital to the development of marine natural products (MNP) as therapeutic leads. One of the more time consuming aspects of MNP research arises in the connection between structure and function. Here, we describe an isolation protocol that adapts tumor cell proteomes as a vehicle for MNP isolation therein uniting structural and functional analysis. Application of this method to extracts of the sponge Agelas conifera led to the isolation of a unique poly-hydroxybutyrated β-galactosphingolipid, coniferoside.

Methoxycarbonylation of olefins catalysed by homogeneous palladium(II) complexes of (phenoxy)imine ligands bearing alkoxy silane groups

The Schiff base compounds 2-phenyl-2-((3(triethoxysilyl)propyl)imino)ethanol (HL1) and 4-methyl-2-((3(triethoxysilyl)propyl)imino)methyl)phenol (HL2) were synthesized via condensation reactions of a suitable ketone or aldehyde and (3-aminopropyl) triethoxy silane (APTES). Whereas the reactions of HL1 and HL2 with [Pd(OAc)2] afforded the bis(chelated) palladium compounds [Pd(L1)2] (1) and [Pd(L2)2] (2), treatments of HL1 and HL2 with [Pd(NCMe)2Cl2] gave the mono(chelated) complexes [Pd(HL1)2Cl2] (3) and [Pd(HL2)2Cl2] (4) respectively. Structural characterization of the compounds was achieved using NMR and FT-IR spectroscopies, mass spectrometry and micro-analyses. Complexes 1–4 gave active catalysts in the methoxycarbonylation of higher olefins producing linear esters as the major products. The coordination environment around the palladium center of the complexes dictated the relative catalytic activity, where the bis(chelated) analogues 1 and 2 were more active than the mono(chelated) analogues 3 and 4. The nature of the acid promoter, phosphine groups, solvent system, olefin substrate and reactions conditions influenced the catalytic behaviour of the complexes.

FURTHER STUDIES ON THE UTILITY OF SODIUM HYPOCHLORITE IN ORGANIC SYNTHESIS. SELECTIVE OXIDATION OF DIOLS AND DIRECT CONVERSION OF ALDEHYDES TO ESTERS

Sodium hypochlorite in acetic acid solution selectively oxidizes secondary alcohols to ketones in the presence of primary alcohols and converts aldehydes to methyl esters in the added presence of methanol.

Pd-catalysed formation of ester products from cascade reaction of 5-hydroxymethylfurfural with 1-hexene

A cascade reaction involving decarbonylation of 5-hydroxymethylfurfural (HMF) followed by methoxycarbonylation of 1-hexene produces methyl heptanoate (MH) using a catalytic system composed of a Pd-phosphine complex and methanesulfonic acid (MSA) co-catalyst at moderate reaction temperature. Concomitant hydration of HMF followed by hydrogenation of methyl levulinate (ML) to γ-valerolactone (GVL) occurs with the catalytic system under the same reaction conditions using HMF and methanol as the source of CO and H2, respectively. Under optimized reaction conditions, about 50% of MH along with 12% ML and 35% GVL is obtained from HMF using Pd-(1,2-bis(di-tert-butylphosphinomethyl)benzene) (DTBPMB), MSA and 1-hexene in methanol at 120 °C. Interestingly, sugars, such as glucose, fructose and xylose, are able to be converted to MH, ML and GVL as well. Isotopic labeling studies with 13C1-fructose in methanol-d4 and 13C-methanol-d4 confirm that H2 originates from methanol, while CO generates predominantly from the formyl group of the HMF formed by fructose dehydration.

Palladium(II) complexes of (pyridyl)imine ligands as catalysts for the methoxycarbonylation of olefins

Reactions of 2-methoxy-N-((pyridin-2-yl)methylene)ethanamine (L1), 2-((pyridin-2-yl)methyleneamino)ethanol (L2) and 3-methoxy-N-((pyridin-2-yl)methylene)propan-1-amine (L3) ligands with either [PdCl2(COD)] or [PdCl(Me)(COD)] produced the corresponding monometallic complexes [PdCl2(L1)] (1), [PdClMe(L1)] (2), [PdCl2(L2)] (3) and [PdCl2(L3)] (4). The solid state structure of complex 1 confirmed the bidentate coordination mode of L1, giving a distorted square planar geometry. All the complexes (1–4) formed active catalysts for the methoxycarbonylation of higher olefins to give linear and branched esters. The catalytic behavior of complexes 1–4 were influenced by both the complex structure and olefin chain length.