1189-09-9

Basic information

• Product Name: METHYL GERANATE
• Synonyms: 2,6-Octadienoic acid, 3,7-dimethyl-, methyl ester, (E)-;3,7-dimethyl-,methylester,(e)-6-octadienoicacid;6-Octadienoicacid,3,7-dimethyl-,methylester,(E)-2;E-Methylgeranate;Methyl (2E)-3,7-dimethyl-2,6-octadienoate;methyl (E)-2,6-octadienoate, 3,7-dimethyl;methyl (E)-geraniate;Methyl 2,6-octadienoate, 3,7-dimethyl, (E)-
• CAS NO: 1189-09-9
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.26
• EINECS: 214-712-6
• Mol File: 1189-09-9.mol

Chemical Properties

• Boiling Point: 70°C/4mm
• Flash Point: 70°C/4mm
• Appearance: /
• Density: 0.925
• Vapor Pressure: 0.0257mmHg at 25°C
• Refractive Index: 1.4690
• CAS DataBase Reference: METHYL GERANATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL GERANATE(1189-09-9)
• EPA Substance Registry System: METHYL GERANATE(1189-09-9)

Safety Data

• TSCA: Yes
• Hazardous Substances Data: 1189-09-9(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
Methyl geranate is used as a fragrance ingredient for its ability to add richness and naturalness to floral scents. It is particularly effective in colognes, especially when combined with neroli and green notes, as well as with galbanum. It is also useful in imparting a natural note in re-constituted oils.
Used in Perfumery:
Methyl geranate is used as a fixative agent in perfumery, helping to extend the longevity of fragrances and enhance their overall quality. Its usage levels range from 0.5% to 10%, depending on the desired effect and the specific formulation.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 269, 1975 DOI: 10.1021/jo00890a034Journal of the American Chemical Society, 90, p. 5616, 1968 DOI: 10.1021/ja01022a059

InChI:InChI=1/C11H18O2/c1-9(2)6-5-7-10(3)8-11(12)13-4/h6,8H,5,7H2,1-4H3/b10-8+

Upstream product

• 6443-91-0 ethynyl methyl ether 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 5927-18-4 trimethyl phosphonoacetate 
• 65688-80-4 (E)-7-Bromo-3,7-dimethyl-oct-2-enoic acid methyl ester 
• 4698-08-2 (E)-geranic acid 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 106-24-1 Geraniol 
• 75-16-1 methylmagnesium bromide 
• 116927-05-0 Methyl (Z)-7-Methyl-3-phenylthio-2,6-octadienoate 
• 88226-96-4 2-Isopropenyl-3,3-dimethyl-pent-4-enoic acid methyl ester 
• 203204-92-6 methyl (2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienoate 

Downstream Products

• 106-24-1 Geraniol 
• 49815-58-9 6,6-dimethyl-2-methyl-1-cyclohexene-1-carboxylic acid methyl ester 
• 28043-10-9 methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate 
• 73114-22-4 (6E,10E)-9-Benzenesulfonyl-2,6,11,15-tetramethyl-hexadeca-2,6,10,14-tetraen-8-one 
• 53155-88-7 C₂₁H₃₅NO₃ 
• 57683-64-4 (2E,6E)-9-Methoxycarbonyl-3,7-dimethyl-deca-2,6-dienedioic acid dimethyl ester 
• 20483-42-5 2,6,6-Trimethyl-5-propionyl-cyclohex-2-enecarboxylic acid methyl ester 
• 20589-57-5 5-(2,2-Dimethyl-propionyl)-2,6,6-trimethyl-cyclohex-2-enecarboxylic acid methyl ester 
• 2270-60-2 methyl 3,7-dimethyloct-6-enoate 
• 57683-65-5 (2E,6E)-9-Benzenesulfonyl-3,7-dimethyl-9-(2-methyl-propenyl)-deca-2,6-dienedioic acid dimethyl ester 
• 20483-43-6 5-Isobutyryl-2,6,6-trimethyl-cyclohex-2-enecarboxylic acid methyl ester 
• 50502-46-0 methyl (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enoate 
• 1862-61-9 methyl nerate 
• 21634-63-9 methyl methyl-2-(1-methylethenyl)-2-hexenoate 

Relevant articles and documents

Synthesis of d8-geranyl diphosphate

Multiply labelled d8-geranyl diphosphate (3-methyl-7- 2H3-methyl-[1,1,8,8,8]-2H5-2E,6- octadienyl diphosphate) was synthesised from geraniol in 8 steps. Geraniol was converted to [1,1]-2H2-geraniol by a three step oxidation-reduction sequence in 38% yield. Selective epoxidation of [1,1]- 2H2-geranyl acetate gave 6,7-epoxy-[1,1]- 2H2-geranyl acetate, which, on oxidative cleavage of the epoxide and Wittig elaboration with d6-isopropyl triphenylphosphorane, gave d8-geraniol (14% yield) which was, in turn, converted to the title compound. Copyright

Total Synthesis of (-)-Sinulariadiolide. A Transannular Approach

The constrained tricyclic skeleton of the nor-cembranoid sinulariadiolide (1) with a nine-membered nexus was obtained by a cascade of transannular Michael reaction, carbonate elimination, butenolide formation, and spontaneous oxa-Michael addition of MeOH. The required macrocyclic precursor was prepared by ring-closing alkyne metathesis followed by trans-hydrostannation/carbonylation.

Biosyntheses of geranic acid and citronellic acid from monoterpene alcohols by Saccharomyces cerevisiae

Geraniol is one of the important aromatic ingredients in alcoholic beverages. Bioconversions of geraniol to other terpenoids and genes involved in the oxidation of geraniol were investigated. Geranic acid and citronellic acid were detected in yeast culture, where geraniol or nerol was added. Addition of citral, a mixture of geranial and neral, resulted in the production of geranic acid and citronellic acid, whereas the addition of citral or citronellal resulted in the production of citronellic acid, suggesting that citronellic acid might be produced through the conversion of citral to citronellal followed by the oxidation of citronellal. Consumption of geraniol and production of geranic acid, citronellic acid, and citronellol were affected in adh1Δ, adh3Δ, adh4Δ, and sfa1Δyeast strains, which possess single deletion of a gene encoding alcohol dehydrogenase. This is the first report of the bioconversion of monoterpene alcohols, geraniol and nerol, to geranic acid and citronellic acid in yeast culture.

N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading

We report the discovery that simple carboxylic acids, such as benzoic acid, boost the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes. A simple and efficient protocol for the transformation of a wide range of sterically hindered α- and β-substituted aliphatic aldehydes/enals, catalyzed by a novel and readily accessible N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt, and benzoic acid as co-catalyst, was developed. A whole series of α/β-substituted aliphatic aldehydes/enals hitherto not amenable to NHC-catalyzed esterification could be reacted at typical catalyst loadings of 0.02–1.0 mol %. For benzaldehyde, even 0.005 mol % of NHC catalyst proved sufficient: the lowest value ever achieved in NHC catalysis. Preliminary studies point to carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates as the mechanistic basis of the observed effect.

Stereocontrolled synthesis and configurational assignment of (R)-all-trans-11,12-dihydro-3-hydroxyretinol

The synthesis of (R)-all-trans-11,12-dihydro-3-hydroxyretinol and putative metabolites of the side-chain functional group has been achieved in a stereocontrolled manner via the Suzuki-Hiyama cross-coupling reaction of an enantiopure (hydroxycyclohexenyl)alkenyliodide and non-conjugated pinacolboranedienoate, which allowed the absolute configuration of this natural product to be confirmed.

Divergent synthesis of four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid, esters and evaluation for the antifungal activity

The four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid 2 were synthesized via the selective direct Sharpless asymmetry dihydroxylation of geraniol as the key step in 35.0%-48.0% overall yields with 91.9%-97.7% ee values for esters 4 and 31.3%-36.4% overall yields with 90.3-97.5% ee values for acids 2 using cis- and trans-geraniol as raw materials. Their structures were characterized by 1H, 13C NMR and HR-ESI-MS data. The in vivo bioassay results showed that the chiral acid (Z, S)-2 was a good lead compound with 80%-100% inhibitory rates against P. cubensis, E. graminis, P. sorghi and C. gloeosporioides at the concentration of 400μg/mL.

PLANT OR MICROORGANISM-DERIVED CAROTENOID-OXYGEN COPOLYMER COMPOSITIONS, METHODS OF IDENTIFYING, QUANTIFYING AND PRODUCING SAME AND USES THEREOF

The present invention relates to carotenoid-oxygen copolymers, compositions, methods of identifying and quantifying carotenoid-oxygen copolymers in food and related sources, and methods of producing compositions comprising same. In one aspect the method of identifying and quantifying carotenoid-oxygen copolymers comprises an analysis of a low molecular weight marker compound in said sources. In another aspect the present invention provides a method of preparing compositions comprising said carotenoid-oxygen copolymers and/or enhancing levels of said copolymers in food sources in a sufficient and practically useful concentration to have beneficial effects in animals and humans, including beneficial immunological and health effects.

Studies on [2?+?3] cycloaddition reaction of nitrile oxides to linear dipolarophiles bearing multiple double bonds

Abstract: Site selectivity, regioselectivity, and stereoselectivity of [2?+?3] cycloaddition of benzonitrile oxides to polyunsaturated esters were examined. Site selectivity was correlated with electron charges of unsaturated carbon atoms. Structure of the products has been established by an extensive application of 1H and 13C NMR spectroscopy and electrospray ionization mass spectrometry. Graphical abstract: [Figure not available: see fulltext.]

Catalyzed dehydrogenative coupling of primary alcohols with water, methanol, or amines

A working partnership: Metal-ligand cooperativity is responsible for the high activity of the rhodium amido complex 1 in the dehydrogenative coupling of primary alcohols with water, methanol, or amines, including ammonia (see scheme), to give carboxylic acids, methyl carboxylates, or amides, respectively. The catalysis proceeds under mild reaction conditions in the presence of a recyclable hydrogen acceptor A. The multistep mechanism was elucidated by computational methods. (Chemical Equation Presented)

ANTIMICROBIAL ACTIVE PREPARATIONS

The invention relates to the use of perillic, geranic and citronella acids, the derivatives thereof and citronrllol derivatives in the form of antimicrobial active agents against bacteria, yeast and/or mildew, microorganisms hereafter. Said invention relates, in particular to the use of said antimicrobial active agents for producing cosmetic and pharmaceutical preparations, food product and animal food compounds. Natural monotherpenes and the derivatives of the oxidation products thereof as the antimicrobial active agents are also disclosed.