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
• Article Data: 27

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

Methyl geranate is a key link between the lavender aspect and the geranium character for a fougere note. It gives excellent effects in many florals to develop richness and naturalness and should be tried in colognes especially with neroli and green notes in combination with galbanum. Usage levels: 0.5-10%. It is useful in imparting a natural note in re-constituted oils.

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 
• 33665-33-7 2,4,4-Trimethyl-5-thiophenylcyclohexen-3-carbonsaeure-methylester 
• 50502-46-0 methyl (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enoate 
• 1862-61-9 methyl nerate 

Relevant articles and documents

Stereoselective synthesis of the C-18 cecropia juvenile hormone.

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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.

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.