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 
• 186581-53-3 diazomethane 
• 4698-08-2 (E)-geranic acid 
• 67-56-1 methanol 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 106-24-1 Geraniol 
• 459-80-3 geranic acid 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 870-63-3 prenyl bromide 
• 15681-48-8 lithium dimethylcuprate 
• 79439-50-2 dimethyl 2-(4-methylpent-3-enyl)maleate 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 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 
• 106-25-2 Nerol 
• 106-24-1 Geraniol 
• 116036-07-8 1,2,5-trimethyl-2-hydroxy-6-methoxycarbonylcyclohexane 
• 28043-10-9 methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate 
• 81752-87-6 methyl (+/-)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate 
• 49815-58-9 6,6-dimethyl-2-methyl-1-cyclohexene-1-carboxylic acid methyl ester 
• 50502-46-0 methyl (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enoate 
• 70451-58-0 Benzoic acid 1-methoxycarbonyl-6-methyl-2-methylene-hept-5-enyl ester 
• 150-86-7 phytol 

Relevant articles and documents

Stereoselective synthesis of the C-18 cecropia juvenile hormone.

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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.