5949-05-3

Usage

Uses

1. Used in Pharmaceutical Industry:
(-)-CITRONELLAL is used as a key intermediate for the synthesis of bioactive compounds. These compounds have potential applications in the development of pharmaceuticals, particularly those targeting specific health conditions.
2. Used in Synthesis of Bioactive Compounds:
(-)-CITRONELLAL is used as a starting material for the synthesis of various bioactive compounds, such as (+)-hexahydrocannabinol, (S)-isopulegol, and machaeriols A and B. These synthesized compounds can be utilized in the development of new drugs or therapeutic agents.
3. Used in Fragrance Industry:
Due to its pleasant and distinctive scent, (-)-CITRONELLAL can be used as a component in the creation of fragrances and perfumes, adding a unique and appealing aroma to these products.
4. Used in Flavor Industry:
(-)-CITRONELLAL can also be employed in the flavor industry, where it can be used to enhance the taste and aroma of various food and beverage products.
5. Used in Cosmetic Industry:
(-)-CITRONELLAL's unique properties make it suitable for use in the cosmetic industry, where it can be incorporated into skincare and beauty products for its potential benefits.

Purification Methods

Fractionally distil it. Alternatively extract it with NaHSO3 solution, wash it with Et2O, then acidify it to decompose the bisulfite adduct and extract with Et2O, dry (Na2SO4), evaporate and distil. Check for purity by hydroxylamine titration. The ORD in MeOH (c 0.167) is: []700 +9o, []589 +11o, []275 +12o and []260 +12o. The semicarbazone has m 85o, and the 2,4-dinitrophenylhydrazone has m 79-80o. [(+)-compound: Tietze & Beifuss Org Synth 71 167 1993, IR: Carroll et al. J Chem Soc 3457 1950, ORD: Djerassi & Krakower J Am Chem Soc 81 237 1959, Beilstein 1 IV 3515.]

InChI:InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m0/s1

Upstream product

• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 82215-37-0 (2R,4R,5S)-3,4-Dimethyl-5-phenyl-2-((E)-styryl)-oxazolidine 
• 67392-54-5 N,N-diethyl-N-{1-[(3S),7-dimethylocta-1,6-dienyl]}amine 
• 64504-53-6 2-methylpent-2-en-5-yl lithium 
• 86297-01-0 (2R,4R,5S)-3,4-Dimethyl-5-phenyl-2-((E)-propenyl)-oxazolidine 
• 693-02-7 hex-1-yne 
• 106-22-9 Citronellol 
• 107297-78-9 (4R,5R)-4,5-Dimethyl-2-((E)-propenyl)-[1,3]dioxolane 
• 2111-53-7 (S)-(-)-citronellic acid 
• 544-17-2 calcium diformate 
• 106-24-1 Geraniol 
• 40267-53-6 (E)-N,N-diethyl-3,7-dimethyl-2,6-octadienylamine 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 

Downstream Products

• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 134876-96-3 (S)-2-(2,6-dimethylhept-5-en-1-yl)-1,3-dioxolane 
• 104870-56-6 (+)-isopulegol 
• 3391-87-5 l-menthone 
• 18309-28-9 (1S,4S)-isomenthone 
• 221632-67-3 (6S)-2,6-dimethyl-8,8-di(phenylthio)oct-2-ene 

Relevant academic research and scientific papers

First total synthesis of three cembrene diterpenoids

The first total synthesis and three diterpenoids of the cembrane class, is described. And the absolute stereochemistry of these natural products is assigned by synthesis.

Investigating the Structure-Reactivity Relationships Between Nicotinamide Coenzyme Biomimetics and Pentaerythritol Tetranitrate Reductase

Ene reductases (ERs) are attractive biocatalysts in terms of their high enantioselectivity and expanded substrate scope. Recent works have proved that synthetic nicotinamide coenzyme biomimetics (NCBs) can be used as easily accessible alternatives to natural cofactors in ER-catalyzed reactions. However, the structure-reactivity relationships between NCBs and ERs and influence factors are still poorly understood. In this study, a series of C-5 methyl modified NCBs were synthesized and tested in the PETNR-catalyzed asymmetric reductions. The physicochemical properties of these NCBs including electrochemical properties, stability, and kinetic behavior were studied in detail. The results showed that hydrophobic interaction caused by the introduced methyl group contributed to the stabilization of binding conformation in enzyme active site, resulting in comparable catalytic activity with that of NADPH. Molecular dynamics and steered molecular dynamics simulations were further performed to explain the binding mechanism between PETNR and NCBs, which revealed that stable catalytic conformation, appropriate donor-acceptor distance and angle, as well as free dissociation energy are important factors affecting the activity of NCBs. (Figure presented.).

Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation

In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.

Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?

The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

Preparation method of optically active citronellal (by machine translation)

The preparation method of the optically active citronellal can significantly improve the catalytic stability, of the optically active transition metal catalyst for homogeneous catalysis to obtain, the optically active citronellal. which is obtained by reacting a transition metal compound with an optically active ligand containing two phosphorus atoms, and, or iron in the substrate material used for the asymmetric hydrogenation reaction . is prepared by reacting a transition metal compound with an optically active ligand containing two phosphorus atoms in the presence of a transition metal catalyst in the preparation method of the optically active citronellal with an asymmetric hydrogenation reaction in the presence of a transition metal catalyst to achieve a higher degree of peripheral speed, ≤6mgKOH/g/of the optically ≤50ppm. active citronellal. (by machine translation)

Method for preparing optically active citronellal (by machine translation)

The invention provides a method, for preparing optically active citronellal by reacting a transition metal catalyst with an asymmetric hydrogenation reaction, to obtain the optically active citronellal, wherein the substrate is neral and/or the vanillic, catalyst is obtained, by controlling the catalytic activity ≤500ppm of the asymmetric hydrogenation reaction substrate and remarkably improving the service life of the catalyst by controlling the asymmetric hydrogenation reaction substrate through oxidation . and ≤10ppm, or the aqueous chlorine, catalyst obtained by reacting the transition metal compound with the optically, active ligand containing .the two phosphorus atoms to obtain the optically active citronellal. (by machine translation)

Iridium-Catalyzed Asymmetric Isomerization of Primary Allylic Alcohols Using MaxPHOX Ligands: Experimental and Theoretical Study

The asymmetric isomerization of primary allylic alcohols to chiral aldehydes using iridium-catalysts bearing P,N-MaxPHOX ligands has been studied. These catalysts can be fine-tuned as they present three different stereogenic centers to modulate both the reactivity and enantioselectivity of a family of different substrates. The experimental part is supported by a DFT study of the reaction mechanism, which provides new insights into the key steps of this transformation.

Amides as bioisosteres of triazole-based geranylgeranyl diphosphate synthase inhibitors

Geranylgeranyl diphosphate synthase (GGDPS) inhibitors are of potential therapeutic interest as a consequence of their activity against the bone marrow cancer multiple myeloma. A series of bisphosphonates linked to an isoprenoid tail through an amide linkage has been prepared and tested for the ability to inhibit GGDPS in enzyme and cell-based assays. The amides were designed as analogues to triazole-based GGDPS inhibitors. Several of the new compounds show GGDPS inhibitory activity in both enzyme and cell assays, with potency dependent on chain length and olefin stereochemistry.

Chiral amorphous metal–organic polyhedra used as the stationary phase for high-resolution gas chromatography separations

Herein, we describe a new chiral amorphous metal–organic polyhedra used as the stationary phase for high-resolution gas chromatography (GC). The chiral stationary phase was coated onto a capillary column via a dynamic coating process and investigated for a variety of compounds. The experimental results showed that the chiral stationary phase exhibits good selectivity for linear alkanes, linear alcohols, polycyclic aromatic hydrocarbons, isomers, and chiral compounds. In addition, the column has the advantages of high column efficiency and short analysis time. The present work indicated that amorphous metal–organic polyhedra have great potential for application as a new type of stationary phase for GC.