3971-54-8

Basic information

• Product Name: METHYL CIS-9,10-METHYLENEOCTADECANOATE
• Synonyms: METHYL DIHYDROSTERULATE;METHYL CIS-9,10-METHYLENEOCTADECANOATE;(+/-)-cis-9,10-methyleneoctadecanoic*acid methyl;Methyl cis-8-(2-octylcyclopropyl)octanoate;Cyclopropaneoctanoic acid, 2-octyl-, methyl ester, cis-;Methyl 2-octylcyclopropaneoctanoate cis-;Methyl cis-9,10-methylene-octadecanoate (Methyl dihydrosterculate);cis-9,10-Methyleneoctadecanoic Acid methyl ester
• CAS NO: 3971-54-8
• Molecular Formula: C20H38O2
• Molecular Weight: 310.51
• Mol File: 3971-54-8.mol

Chemical Properties

• Boiling Point: 362.7 °C at 760 mmHg
• Flash Point: 178.1 °C
• Appearance: /
• Density: 0.896 g/cm³
• Vapor Pressure: 1.9E-05mmHg at 25°C
• Refractive Index: 1.457
• CAS DataBase Reference: METHYL CIS-9,10-METHYLENEOCTADECANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL CIS-9,10-METHYLENEOCTADECANOATE(3971-54-8)
• EPA Substance Registry System: METHYL CIS-9,10-METHYLENEOCTADECANOATE(3971-54-8)

Safety Data

• Hazardous Substances Data: 3971-54-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H38O2/c1-3-4-5-6-8-11-14-18-17-19(18)15-12-9-7-10-13-16-20(21)22-2/h18-19H,3-17H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 75-11-6 diiodomethane 
• 112-62-9 Methyl oleate 
• 67-56-1 methanol 
• 4675-61-0 8-((cis)-2-octylcyclopropyl)octanoic acid 
• 112-80-1 cis-Octadecenoic acid 
• 29203-99-4 trans-10-(2-octylcyclopropyl)octanoic acid 

Downstream Products

• 4675-61-0 8-((cis)-2-octylcyclopropyl)octanoic acid 

Relevant articles and documents

Synthesis and thermophysical properties of ionic liquids: Cyclopropyl moieties versus olefins as Tm-reducing elements in lipid-inspired ionic liquids

Cyclopropyl moieties embedded in the long aliphatic side chains of imidazolium-type ionic liquids are shown to be highly effective in lowering the Tm of such materials relative to counterparts bearing linear, saturated side chains. While not as efficient as olefins in bringing about this effect, ILs incorporating side-chain cyclopropanated modules are likely to be more resistant to aerobic degradation than those employing the former.

Preparation of fatty acid methyl esters for gas-liquid chromatography

A convenient method using commercial aqueous concentrated HCl (conc. HCl; 35%, w/w) as an acid catalyst was developed for preparation of fatty acid methyl esters (FAMEs) from sterol esters, triacylglycerols, phospholipids, and FFAs for gas-liquid chromatography (GC). An 8% (w/v) solution of HCl in methanol/water (85:15, v/v) was prepared by diluting 9.7 ml of conc. HCl with 41.5 ml of methanol. Toluene (0.2 ml), methanol (1.5 ml), and the 8% HCl solution (0.3 ml) were added sequentially to the lipid sample. The final HCl concentration was 1.2% (w/v). This solution (2 ml) was incubated at 45°C overnight or heated at 100°C for 1-1.5 h. The amount of FFA formed in the presence of water derived from conc. HCl was estimated to be 1.4%. The yields of FAMEs were ≥96% for the above lipid classes and were the same as or better than those obtained by saponification/methylation or by acid-catalyzed methanolysis/ methylation using commercial anhydrous HCl/ methanol. The method developed here could be successfully applied to fatty acid analysis of various lipid samples, including fish oils, vegetable oils, and blood lipids by GC. Copyright

The newly synthesized linoleic acid derivative FR236924 induces a long-lasting facilitation of hippocampal neurotransmission by targeting nicotinic acetylcholine receptors

The newly synthesized linoleic acid derivative, FR236924, induces a long-lasting facilitation of hippocampal neurotransmission based on a persistent enhancement in the activity of presynaptic nicotinic ACh receptors via a PKC pathway and the ensuing increase in glutamate release, not only in vitro but in vivo at a low dosage (2 mg/kg, ip), which suggested the possibility of its use as a promising anti-dementia drug.

New family of cyclopropanating reagents: Synthesis, reactivity, and stability studies of iodomethylzinc phenoxides

A valuable alternative to the traditional Simmons-Smith reagents is offered by the title compounds, as a result of their ease of preparation and high reactivities towards unfunctionalized olefins (see scheme).

Ultrasound in Lipids. Furan Formation under Ultrasonic assisted Simmons-Smith Reaction and the Effect of Cadmium and Copper as Zinc Replacers

Methyl 12-oxo-octadec-9-cis-enoate gave methyl 9,12-epoxyoctadeca-9,11-dienoate when treated with zinc or cadmium in the presence of di-iodomethane and 1,2-dimethoxyethane under concomitant ultrasonic irradiation, while under similar conditions copper caused cyclopropanation across the ethylenic bond in methyl oleate and ricinoleate.

A facile, versatile procedure for the preparation of fatty acid esters suitable for glc or hplc analyses

The preparation of fatty acid methyl esters for glc analyses and of various aryl esters for hplc analyses has traditionally been carried out in totally unrelated operations.This paper draws attention to the use of fatty acid-trifluoroacetic acid mixed anhydrides which may be directly and efficiently converted into either type of esters.The utility of the method was demonstrated by the preparation of series of methyl, 2-naphthyl, and vanillin fatty acid esters.The spectral characterization of some aryl fatty acid esters is recorded.