1931-63-1

Basic information

• Product Name: 9-OXO-NONANOIC ACID METHYL ESTER
• Synonyms: 9-OXO-NONANOIC ACID METHYL ESTER;8-Formyloctanoic acid methyl ester;9-Ketononanoic acid methyl ester;Methyl 9-oxononanoate;Methyl 9-Oxononanoate (90%);HOC(CH2)7CO2Me
• CAS NO: 1931-63-1
• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.24812
• Mol File: 1931-63-1.mol
• Article Data: 98

Chemical Properties

• Boiling Point: 249.4°Cat760mmHg
• Flash Point: 101.8°C
• Appearance: /
• Density: 0.958g/cm³
• Vapor Pressure: 0.023mmHg at 25°C
• Refractive Index: 1.431
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• Stability: Air Sensitive, Hygroscopic
• CAS DataBase Reference: 9-OXO-NONANOIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 9-OXO-NONANOIC ACID METHYL ESTER(1931-63-1)
• EPA Substance Registry System: 9-OXO-NONANOIC ACID METHYL ESTER(1931-63-1)

Safety Data

• Hazardous Substances Data: 1931-63-1(Hazardous Substances Data)

Usage

Uses

Methyl 9-Oxononanoate is a linseed oil-based coating. It is solventless polymeric protective.

Synthesis Reference(s)

Synthesis, p. 563, 1993 DOI: 10.1055/s-1993-25903

InChI:InChI=1/C10H18O3/c1-13-10(12)8-6-4-2-3-5-7-9-11/h9H,2-8H2,1H3

Upstream product

• 544-72-9 9-cis,11-trans,13-cis-octadecatrienoic acid 
• 112-62-9 Methyl oleate 
• 56555-02-3 methyl 9-chloro-9-oxononanoate 
• 1115-01-1 methyl 9,10-dihydroxy stearate 
• 34957-73-8 methyl 9-hydroxynonanoate 
• 2462-84-2 methyl (9E)-octadec-9-enoate 
• 52077-21-1 (8E,1'E,3'Z)-9-(1',3'-nonadienyloxy)-8-nonenoic acid methyl ester 
• 52077-22-2 methyl colnelenate 
• 2566-91-8 epoxidized methyl oleate 
• 140463-19-0 (E)-8-(methoxycarbonyl)octanal O-methyloxime 
• 125180-11-2 8-Dimethylcarbamoyl-octanoic acid methyl ester 
• 333-27-7 methyl trifluoromethanesulfonate 
• 110821-53-9 methyl 9-methoxy-7-nonenoate 
• 6003-08-3 methyl 9,10,16-trihydroxyhexadecanoate 

Downstream Products

• 2104-19-0 azelaic monomethyl ester 
• 58257-45-7 methyl tridec-9-enoate 
• 1120-25-8 (Z)-9-hexadecenoic acid methyl ester 
• 24753-52-4 18-Hydroxyoleic acid 
• 16195-77-0 α-Elaeostearinsaeuremethylester 
• 301-00-8 methyl linolenate 
• 5746-59-8 (S)-(+)-14-methylhexadecanoic acid 
• 158835-75-7 13-(13-tert-Butoxycarbonylamino-3-hydroxy-10-hydroxymethyl-2-methyl-tridecanoylamino)-3-hydroxy-10-hydroxymethyl-2-methyl-tridecanoic acid pentafluorophenyl ester 
• 20701-68-2 (9Z)-octadec-9-enedioic acid 
• 35153-15-2 (Z)-9-tetradecen-1-ol 
• 16725-53-4 (Z)-9-tetradecen-1-yl acetate 
• 23192-82-7 (E)-tetradec-9-en-1-yl acetate 
• 6084-82-8 9-hydroxy-(10E,12Z)-octadecadien-1-oic acid methyl ester 
• 64660-84-0 cis-9-cetyl myristoleate 

Relevant articles and documents

N-(17-Acyloxy-acyl)-glutamines: Novel Surfactants from Oral Secretions of Lepidopteran Larvae

N-(17-Acyloxy-acyl)-glutamine conjugates such as N-(17-linolenoyloxy-linolenoyl)-glutamine (6), N-(17-linolenoyloxy-linoleoyl)-glutamine (7), N-(17-linoleoyloxy-linolenoyl)-glutamine (8), and N-(17-linoleoyloxy-linoleoyl)-glutamine (9) were identified as novel surfactants in the oral secretion of several lepidopteran larvae (S. exigua, S. littoralis, S. frugiperda, and H. virescens) by LC-MS/MS and chemical degradation. Authentic reference compounds were synthesized via a dissymmetric bis-Wittig approach and confirmed the assigned structures.

Stereocontrolled synthesis of the PPAR-γ agonist 10-nitrolinoleic acid

(Figure presented) The naturally occurring PPAR-γ ligand 10-nitrooctadeca-9(E),12(Z)-dienoic acid (10-nitrolinoleic acid) (2a) was prepared as a single regio- and geometrical isomer in a practical eight-step, convergent sequence. The synthetic route featured a nitro aldol reaction between 9-oxononanoic acid methyl ester (3) and 1-nitronon-3(Z)-ene (4) in the key carbon-carbon bond forming step. The ability of 2a (and its methyl ester 9) to bind to PPAR-γ in a ligand-binding assay is reported.

Total Synthesis of α-Ketol Derivative of Linolenic Acid (KODA), a Flower-inducing Factor in Lemna paucicostata

Racemic 9-hydroxy-10-oxo-12(Z), 15(Z)-octadecadienoic acid [(±)-KODA] was synthesized via a coupling reaction between a diyne and an epoxide derived from methyl oleate as a key step. An optically active 9R-KODA was also synthesized by enantioselective lipase-catalyzed esterification of an allyl alcohol. Both synthetic (±)-KODA and 9K-KODA showed remarkable flower-inducing activity in Pharbitis nil.

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Synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide

Herein, a new protocol for rapid synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide is described. This approach comprises two sequential chemoselective reactions between sulfonium and phosphonium ylides and two distinct aldehydes, which allows for the rapid construction of a variety of unsymmetric α,β-unsaturated epoxy ketones. This methodology allows the rapid construction of the core reactive functionality of a family of lipid peroxidation products, the epoxyketooctadecenoic acids, but can be further broadly utilized as a useful synthon for the synthesis of natural products, particularly those derived from oxidized fatty acids. Accordingly, a protocol utilizing this approach to synthesize the epoxyketooctadecenoic acid family of molecules is described.

Total synthesis and anti-inflammatory bioactivity of (?)-majusculoic acid and its derivatives

The first total synthesis of marine natural product, (?)-majusculoic acid (1) and its seven analogs (9–15), was accomplished in three to ten steps with a yield of 3% to 28%. The strategy featured the application of the conformational controlled establishment of the trans-cyclopropane and stereochemical controlled bromo-olefination or olefination by Horner–Wadsworth–Emmons (HWE) reaction. The potential anti-inflammatory activity of the eight compounds (1 and 9–15) was evaluated by determining the nitric oxide (NO) production in the lipopolysaccharide (LPS)-induced mouse macrophages RAW264.7. (?)-Majusculoic acid (1), methyl majusculoate (9), and (1R,2R)-2-((3E,5Z)-6-bromonona-3,5-dien-1-yl)cyclopropane-1-carboxylic acid (12) showed significant effect with inhibition rates of 33.68%, 35.75%, and 43.01%, respectively. Moreover, they did not show cytotoxicity against RAW264.7 cells, indicating that they might be potential anti-inflammatory agents.