502-47-6

Usage

Uses

Used in Flavor and Fragrance Industry:
Citronellic acid is used as a flavoring agent for its mild, floral, rosy, and fruity melon taste characteristics, making it suitable for enhancing the taste of various food products.
Citronellic acid is also used as a fragrance ingredient for its green-grassy odor and its ability to add a slight citronella nuance, vegetative, and tobacco nuances to perfumes and other scented products.
Used in Chemical Synthesis:
Citronellic acid is used as a chemical intermediate in the synthesis of various compounds, such as stereoisomers of 3,11-dimethylnonacosan-2-one and 29-hydroxy-3,11-dimethylnonacosan-2-one.
Used in Natural Products:
Citronellic acid can be found in several natural sources, including Java citronella, geranium, Borosma pulchellum, Xanthoxylum piperitum, bitter-orange leaves, lemongrass, Calytrix virgata, and Calytrix tetragona leaves. The l-form has been identified in cypress oil (Callitirs glauca R. Br.), Callitirs intratropica, in the oil of Chamaecyparis obtusa, and of Thujopsis dolabrata. The d,l-form is isolated from camphor oil and has also been reported in mandarin peel oil, swangi (Citrus hystrix D.C.), peppermint oil, and black tea.

Preparation

By oxidation of citronellal; also by the conversion of pulegone.

InChI:InChI=1/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)/p-1/t9-/m1/s1

Upstream product

• 2385-77-5 (R)-Citronellal 
• 459-80-3 geranic acid 
• 106-22-9 Citronellol 
• 3068-88-0 4-methyloxetan-2-one 
• 37586-57-5 4-methyl-3-pentenylmagnesium bromide 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 152481-67-9 2-(1,5-Dimethyl-hex-4-enyl)-malonic acid 
• 4613-38-1 nerolic acid 
• 3209-78-7 5,5-dimethoxy-pentan-2-one 
• 56422-95-8 ethyl-2-carbethoxy-3,7-dimethyl-oct-6-enoate 
• 996-82-7 sodium diethylmalonate 
• 99863-63-5 6-amino-3,7-dimethyl-octanoic acid 
• 152481-62-4 ethyl 2-ethoxycarbonyl-3-methyl-6,6-dimethoxyhexanoate 
• 152481-59-9 ethyl 2-ethoxycarbonyl-3-methyl-6,6-dimethoxy2-hexenoate 

Downstream Products

• 3664-64-0 rac-4,8-dimethyl-7-nonen-2-one 
• 115033-76-6 Se-phenyl 3,7-dimethyloct-6-eneselenoate 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 32531-52-5 3,7-dimethyloctanoic acid 
• 2385-77-5 (+)-citronellal 
• 136735-59-6 benzyl 3,7-dimethyloct-6-enoate 
• 131506-90-6 tert-butyl 5,9-dimethyl-3-oxo-2-(triphenylphosphoranylidene)-8-decenoate 
• 3058-01-3 3-methyladipic acid 
• 1428743-63-8 4-(3,7-dimethyl-6-octenoyl)phenyl 3,7-dimethyl-6-octenoate 
• 1428743-64-9 1-(4-fluorophenyl)-3,7-dimethyl-6-octen-1-one 
• 26728-45-0 isopropyl 3,7-dimethyl-6-octenoate 
• 2270-60-2 methyl 3,7-dimethyloct-6-enoate 
• 220445-69-2 2-diazo-N-benzyl-N-(3,7-dimethyloct-6-enoyl)malonamic acid ethyl ester 
• 220445-68-1 N-benzyl-N-(3,7-dimethyloct-6-enoyl)malonamic acid ethyl ester 

Relevant academic research and scientific papers

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

Method for preparing carboxylic acid by catalyzing aldehyde oxidation with N-heterocyclic carbene

The invention discloses a method for preparing carboxylic acid by catalyzing aldehyde oxidation with N-heterocyclic carbene, and relates to the field of catalytic technology. The method comprises thefollowing steps: taking deionized water as a solvent and aldehyde as a reaction substrate, adding alkali into a reaction system, taking air as an oxidant and N-heterocyclic carbene as a catalyst required by the reaction, and carrying out catalytic oxidation on aldehyde at room temperature to 80 DEG C to generate a corresponding reaction product. The method has the beneficial effects that the N-heterocyclic carbene is used as the catalyst, no organic solvent is needed in the reaction process, the reaction process is green and safe, and the reaction yield is high.

Replacement of an Indole Scaffold Targeting Human 15-Lipoxygenase-1 Using Combinatorial Chemistry

Human 15-lipoxygenase-1 (15-LOX-1) belongs to the class of lipoxygenases, which catalyze oxygenation of polyunsaturated fatty acids, such as arachidonic and linoleic acid. Recent studies have shown that 15-LOX-1 plays an important role in physiological processes linked to several diseases such as airway inflammation disease, coronary artery disease, and several types of cancer such as rectal, colon, breast and prostate cancer. In this study, we aimed to extend the structural diversity of 15-LOX-1 inhibitors, starting from the recently identified indolyl core. In order to find new scaffolds, we employed a combinatorial approach using various aromatic aldehydes and an aliphatic hydrazide tail. This scaffold-hopping study resulted in the identification of the 3-pyridylring as a suitable replacement of the indolyl core with an inhibitory activity in the micromolar range (IC50=16±6 μm) and a rapid and efficient structure–activity relationship investigation.

Modified liquid–liquid interface cultivation system with floating microspheres and binder micro-pieces for slow-growing or unicellular microorganisms: Application to interfacial bioconversions with an actinomycete and yeasts

Liquid–liquid interface bioreactor (L–L IBR) is a unique non-aqueous bioconversion system which comprises a hydrophobic organic solvent (upper phase), a fungal cells–floating microspheres (MS) layer (middle phase), and a liquid medium (lower phase). In this study, a modified L–L IBR with actinomycetes and yeasts was developed by using binder micro-pieces (BM) and estimated its availability through some bioconversions. This modified interface cultivation system was named a tacky liquid–liquid interface bioreactor (L–L IBRtac). After the detailed estimation of its characteristics, the system was applied to oxidation of citronellol to citronellal, 2-methylcyclohexanol to 2-methylcyclohexanone, and 2-octanol to 2-octanone with Rhodococcus hoagii NBRC 3730, oxidation of citronellal to citronellic acid with Candida viswanathii NBRC 10321, and transacetylation of citronellol by acetyl coenzyme A (acetyl-CoA) produced from glucose by Pichia kluyveri NBRC 1165. The accumulation of citronellal, 2-methylcyclohexanone, and 2-octanone reached 3.1 (16 days), 2.3 (12 days), and 32.9 g/l (12 days) in spite of strong biotoxicities of the substrates/products without collapse of a cells–MS–BM layer. On the other hand, 6.1 g/l of citronellic acid and 2.8 g/l of citronellyl acetate were produced from 5% citronellal and 10% citronellol for 12 days, respectively.

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.

Oxidative Transformations of Biosourced Alcohols Catalyzed by Earth-Abundant Transition Metals

The catalytic acceptorless dehydrogenative oxidation of biosourced alcohols into carboxylic acid salts was achieved using earth-abundant Fe and Mn complexes that feature aliphatic PNP pincer ligands in good to excellent yields. The Fe derivatives were characterized by using 57Fe NMR spectroscopy. Mn pincer catalysts are catalytically more efficient than their Fe counterparts thanks to their robustness under basic conditions. Attempts to generate aldehydes from alcohols were not successful using the Fe and Mn species, but a commercially available Ru analogue achieves this transformation selectively under very mild conditions in the presence of a large excess of acetone as a hydrogen acceptor.

Catalytic Fehling's Reaction: An Efficient Aerobic Oxidation of Aldehyde Catalyzed by Copper in Water

The first example of homogeneous copper-catalyzed aerobic oxidation of aldehydes is reported. This method utilizes atmospheric oxygen as the sole oxidant, proceeds under extremely mild aqueous conditions, and covers a wide range of various functionalized aldehydes. Chromatography is generally not necessary for product purification.

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.

Nitrous Oxide as a Hydrogen Acceptor for the Dehydrogenative Coupling of Alcohols

The oxidation of alcohols with N2O as the hydrogen acceptor was achieved with low catalyst loadings of a rhodium complex that features a cooperative bis(olefin)amido ligand under mild conditions. Two different methods enable the formation of either the corresponding carboxylic acid or the ester. N2 and water are the only by-products. Mechanistic studies supported by DFT calculations suggest that the oxygen atom of N2O is transferred to the metal center by insertion into the Rh-H bond of a rhodium amino hydride species, generating a rhodium hydroxy complex as a key intermediate.

Enzyme cascade reactions: Synthesis of furandicarboxylic acid (FDCA) and carboxylic acids using oxidases in tandem

A one-pot tandem enzyme reaction using galactose oxidase M3-5 and aldehyde oxidase PaoABC was used to convert hydroxymethylfurfural (HMF) to the pure bioplastics precursor FDCA in 74% isolated yield. A range of alcohols was also converted to carboxylic acids in high yield under mild conditions.