2270-60-2

Usage

Chemical Description

Methyl citronellate is a derivative of citronellol, a natural acyclic monoterpenoid alcohol found in citronella oil.

Uses

Used in Fragrance Industry:
METHYL CITRONELLATE is used as a fragrance ingredient for its fruity (apple), brandy-like odor, which adds a pleasant and refreshing scent to various products such as perfumes, colognes, and other personal care items.
Used in Flavor Industry:
METHYL CITRONELLATE is used as a flavoring agent for its unique fruity (apple), brandy-like taste, enhancing the flavor profile of food and beverages, particularly those with apple or fruity notes.
Used in Cosmetics Industry:
METHYL CITRONELLATE is used as an additive in the cosmetics industry for its pleasant and refreshing scent, making it a popular choice for products such as lotions, creams, and other skincare items.
Used in Pharmaceutical Industry:
METHYL CITRONELLATE is used as a component in the development of pharmaceutical products, particularly those requiring a fruity (apple), brandy-like odor for improved patient compliance and experience.

Preparation

From citronellic acid, methanol and sulfuric acid; from citronellic acid treated with diazomethane in ether solutuion

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 8649, 1994 DOI: 10.1016/S0040-4039(00)78461-9

InChI:InChI=1/C11H20O2/c1-9(2)6-5-7-10(3)8-11(12)13-4/h6,10H,5,7-8H2,1-4H3/t10-/m0/s1

Upstream product

• 1189-09-9 methyl geranate 
• 121-44-8 triethylamine 
• 186581-53-3 diazomethane 
• 502-47-6 racemic citronellic acid 
• 67-56-1 methanol 
• 36392-06-0 3,7-dimethyl-6-octenoyl chloride 
• 1189-09-9 methyl geranate 
• 1862-61-9 methyl nerate 
• 3209-78-7 5,5-dimethoxy-pentan-2-one 
• 56422-95-8 ethyl-2-carbethoxy-3,7-dimethyl-oct-6-enoate 
• 652162-28-2 Methyl 3-Methyl-6-oxo-2-hexenoate 
• 34680-63-2 (E)-6,6-Dimethoxy-3-methyl-hex-2-enoic acid methyl ester 
• 152481-67-9 2-(1,5-Dimethyl-hex-4-enyl)-malonic acid 
• 152481-59-9 ethyl 2-ethoxycarbonyl-3-methyl-6,6-dimethoxy2-hexenoate 

Downstream Products

• 106-22-9 Citronellol 
• 87803-50-7 Methyl (1α,2α,5β)-2-Methyl-5-(1-methylethenyl)cyclohexanecarboxylate 
• 87803-51-8 Methyl (1β,2α,5β)-2-Methyl-5-(1-methylethenyl)cyclohexanecarboxylate 
• 106-25-2 Nerol 
• 106-24-1 Geraniol 
• 1189-09-9 methyl geranate 
• 106-21-8 tetrahydrogeraniol 
• 485-43-8 (+/-)-iridomyrmecin 

Relevant academic research and scientific papers

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

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.

Aerobic Photooxidative Synthesis of β-Alkoxy Monohydroperoxides Using an Organo Photoredox Catalyst Controlled by a Base

Transition-metal-free synthesis of β-alkoxy monohydroperoxides via aerobic photooxidation using an acridinium photocatalyst was developed. This method enables the synthesis of some novel hydroperoxides. The peroxide source is molecular oxygen, which is cost-effective and atomically efficient. Magnesium oxide plays an important role as a base in the catalytic system.

γ-Lactone Synthesis via Palladium(II)-Catalyzed Lactonization of Unactivated Methylene C(sp3)-H Bonds

A palladium(II)-catalyzed intramolecular lactonization of unactivated methylene C(sp3)-H bonds using PIP bidentate auxiliary is described. This method provides an efficient and concise pathway to synthesize functionalized γ-lactones.

Nickel-catalyzed dehydrogenative cross-coupling: Direct transformation of aldehydes into esters and amides

By exploring a new mode of nickel-catalyzed cross-coupling, a method to directly transform both aromatic and aliphatic aldehydes into either esters or amides has been developed. The success of this oxidative coupling depends on the appropriate choice of catalyst and organic oxidant, including the use of either α,α,α-trifluoroacetophenone or excess aldehyde. Mechanistic data that supports a catalytic cycle involving oxidative addition into the aldehyde C-H bond is also presented.

N-Heterocyclic carbene-catalyzed oxidations

N-Heterocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized, including protected carboxylates. The oxidation proceeds under mild conditions, with low loadings of a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.

N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters

(Chemical Equation Presented) N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield. The reaction proceeds through a transient activated alcohol, which when generated in situ allows for the selective oxidation of the aldehyde under mild conditions. These conditions successfully oxidize potentially epimerizable aldehydes and alcohols while preserving stereochemical integrity. A variety of ester derivatives can be synthesized with variation of the acylated alcohol as well as the unactivated aldehyde.

Regio- and Stereoselective Hydrogenation of Conjugated Carbonyl Compounds via Palladium Assisted Hydrogen Transfer by Ammonium Formate

Excellent regio- and stereoselectivity has been achieved in the hydrogenation of C=C bond conjugated to carbonyl group in presence of olefin by ammonium formate/Pd-C system.

OZONOLYSIS OF ALKENES AND THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS LIII.SYNTHESIS OF THE ESTERS OF 2,3-DIHYDRO DERIVATIVES OF TRI-, DI-, AND MONOPRENOIC ACIDS

The esters of the 2,3-dihydro derivatives of geranylgeranic, farnesylic, and geranic acids (di-, sesqui-, and monoterpenoid acids) were synthesized from the products from ozonolysis of 1,5,9-trimethyl-1E,5E,9E-cyclododecatriene.