18951-85-4

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-Citronellic Acid is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to contribute to the development of novel drugs with potential therapeutic benefits.
Used in Fragrance Industry:
(R)-(+)-Citronellic Acid is used as a key ingredient in the creation of fragrances for its distinct scent properties, enhancing the overall aroma of perfumes, colognes, and other scented products.
Used in Cosmetic Industry:
(R)-(+)-Citronellic Acid is utilized as a component in the formulation of cosmetics for its potential benefits to skin care, such as moisturizing and soothing properties, contributing to the effectiveness of skincare products.
Used in Flavor Industry:
(R)-(+)-Citronellic Acid is employed as a flavoring agent in the food and beverage industry, adding a unique taste to various products, thanks to its characteristic flavor profile.
Used in Agrochemical Industry:
(R)-(+)-Citronellic Acid is used as a component in the development of agrochemicals, such as pesticides and insecticides, leveraging its properties to control and manage pests in agriculture.

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)/t9-/m1/s1

Upstream product

• 2385-77-5 (R)-Citronellal 
• 1117-61-9 (3R)-citronellol 
• 4698-08-2 (E)-geranic acid 
• 55050-39-0 3-Methylene-7-methyloct-6-enoic Acid 
• 4613-38-1 nerolic acid 
• 17882-43-8 (?)-trans-isopulegone 
• 37586-57-5 4-methyl-3-pentenylmagnesium bromide 
• 32082-74-9 (R)-4-methyloxetan-2-one 
• 106-22-9 Citronellol 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 7647-01-0 hydrogenchloride 
• 89-82-7 pulegone 
• 568598-77-6 (R)-citronellic acid 2-oxo-1,2,2-triphenylethyl ester 

Downstream Products

• 1117-61-9 (3R)-citronellol 
• 32531-52-5 3,7-dimethyloctanoic acid 
• 3058-01-3 3-methyladipic acid 
• 89-82-7 pulegone 
• 623-82-5 (R)-3-methylhexanedioic acid 
• 20425-54-1 (R)-1-citronellyl acetate 
• 67214-54-4 (R)-citronellyl tosylate 
• 70200-31-6 (R)-4-methyl-6-(toluene-4-sulfonyloxy)-hexanal 
• 108535-84-8 (R)-3,7-Dimethyl-oct-6-enoic acid ((S)-1-phenyl-ethyl)-amide 
• 163215-96-1 (R)-3,7-Dimethyl-oct-6-enoic acid (R)-3-methyl-cyclohex-2-enyl ester 
• 179685-74-6 (+)-(R)-benzyl-2,6-dimethylhept-5-enylcarbamate 
• 56046-15-2 (R)-7-hydroxycitronellic acid 
• 67-64-1 acetone 
• 568598-77-6 (R)-citronellic acid 2-oxo-1,2,2-triphenylethyl ester 

Relevant academic research and scientific papers

Male-specific sesquiterpenes from phyllotreta flea beetles

Flea beetles in several genera are known to possess male-specific sesquiterpenes, at least some of which serve as aggregation pheromones that attract both sexes. In continuing research on the chemical ecology of Phyllotreta flea beetles, six new male-specific sesquiterpenes were identified, one from P. striolata (hydroxyketone 9) and five from P. pusilla (aldehydes 10-12 and 14 and alcohol 13); both species are crop pests. The minute amounts from beetles provided mass spectra and chromatographic data but were insufficient for complete structure determination. However, it was discovered that the new compounds could all be produced by applying organic reactions to previously identified flea beetle sesquiterpenes, and the resulting, larger amounts of material permitted definitive structure analysis by NMR. Molecular modeling was used in conjunction with NMR to define relative configurations of several newly created stereogenic centers. The absolute configurations of natural 9-14 were established by chiral gas chromatography/mass spectrometry. In electrophysiological tests (GC-EAD) conducted with P. striolata, compound 9 was detected with high sensitivity by the beetle antennae, which is consistent with a pheromonal function. The research opens new possibilities for using behavioral chemicals to monitor or manage these pest species.

Selective PPARδ Modulators Improve Mitochondrial Function: Potential Treatment for Duchenne Muscular Dystrophy (DMD)

The X-ray structure of the previously reported PPARδ modulator 1 bound to the ligand binding domain (LBD) revealed that the amide moiety in 1 exists in the thermodynamically disfavored cis-amide orientation. Isosteric replacement of the cis-amide with five-membered heterocycles led to the identification of imidazole 17 (MA-0204), a potent, selective PPARδ modulator with good pharmacokinetic properties. MA-0204 was tested in vivo in mice and in vitro in patient-derived muscle myoblasts (from Duchenne Muscular Dystrophy (DMD) patients); 17 altered the expression of PPARδ target genes and improved fatty acid oxidation, which supports the therapeutic hypothesis for the study of MA-0204 in DMD patients.

Enantioselective Hydrogenations of a Terpenic Acrylic Acid Catalyzed by Rhodium Complexes of Chiral Diphosphines

Hydrogenations of (E)-3,7-dimethylocta-2,6-dienoic acid ((E)-1) catalyzed by rhodium complexes of the chiral diphosphine (1R,2R)-biscyclobutane (5) in chloride-free methanol (23 deg C, 2-3 atm of H2) were rapid ( 300 turnovers per hour) and gave (S)-(-)-3,7-dimethyloct-6-enoic acid ((S)-(-)-3) in ca. 40-42percent ee.Under the same conditions, (Z)-1 was converted to (R)-(+)-3 in 45percent ee.The Rh-5-catalyzed hydrogenation of (E)-1 in chloride-free methanol was strongly promoted by triethylamine, with maximum rates of ca. 2500 turnovers per hour.The product ena ntiomeric excess was not changed by addition of triethylamine.A study of the amine-promoted hydrogenation of (E)-1 is reported.It is concluded that the carboxylate anion of (E)-1 complexes with rhodium more strongly than does the parent acid and that the resulting rhodium(I) substrate complex adds H2 more rapidly in the deprotonated form.

Syntheses of optically active citronellol, citronellal, and citronellic acid by microbial oxidation and double coupling system in an interface bioreactor

We have already reported that (RS)-Citronellol [(RS)-1] can be optically resolved via a transacetylation with acetyl coenzyme A [acetyl-CoA] by the aid of alcohol acetyltransferase [AATFase] in Pichia kluyveri IFO 1165, which we have referred to as a double coupling system (E value, 30 to 40). In this system, although (R)-1 is obtained at over 98% ee, (S)-Citronellyl acetate [(S)-2] is prepared at 70 to 80% ee. In this article, we report on the conversion of (R)-1 to (R)-Citronellal [(R)-3] and (R)-Citronellic acid [(R)-4] in high yield without racemization by the aid of Rhodococcus equi JCM 6817 and Geotrichum candidum JCM 01747, respectively. On the other hand, the low ee of (S)-1 (78% ee) prepared via the alkaline hydrolysis of (S)-2 is converted to optically active (S)-1 and (S)-4 in high yield with a repeated double coupling system with P. kluyveri IFO 1165 and via enantioselective oxidation with Candida viswanathii IFO 10321, respectively. Thus, five optically active terpenoids related to citronellol, except for (S)-3, were efficiently synthesized via microbial transformations in an interface bioreactor.

Synthesis and stereochemistry of the four himachalene-type sesquiterpenes isolated from the flea beetle (Aphthona flava) as pheromone candidates

Both the (1S,2R) and (1R,2S) isomers of 2,6,6-trimethylbicyclo[5.4.0]undec- 7-en-9-one (1) were synthesized by starting from (S)- and (R)-citronellal (5), respectively. The stereochemistry of (1R,2S)-(-)-1 was established by an X-ray analysis; it exhibits a CD spectrum similar to that of cholest-4-en-3-one, in agreement with its absolute configuration. The ketones (1S,2R)- and (1R,2S)-1 were converted into the en-antiomers of three other himachalene hydrocarbons, 2,2,6-trimethyl-10-methylenebicyclo[5.4.0]undec-1(11)-ene (2), 1,1,5,8-tetramethyl-1,2,3,4,5,6,5a-hepta hydro benzo [1,2-a]-[7]annulene (3), and 1,1,5,8-tetramethyl-1,2,3,4,5-pentahydrobenzo[a][7]annulene (ar-himachalene, 4). The stereochemistry of these himachalene-type sesquiterpenes isolated from flea beetles such as Aphthona flava and Phyllotreta cruciferae as their male-pheromone components was revised to (1S,2R)-1, (6R,7S)-2,(5R,5aS)-3, and (R)-4. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Enantioselective oxidation of racemic citronellol with an interface bioreactor

Microbial oxidation of racemic citronellol was done on the interface between a nutrient agar plate and decane (interface bioreactor). While Rhodococcus accumulated (R)-citronellal (21-80% e.e.), many yeasts accumulated (S)-citronellic acid (20-68% e.e.) as the oxidation product. For the production of (R)-citronellal and (S)-citronellic acid, Rhodococcus equi IFO 3730 and Hansenula anomala IFO 0147 were the best strains, respectively. While citronellol-oxidation in R. equi IFO 3730 was (S)-selective, citronellal-oxidation was (R)-selective. Although H. anomala had also both (S)-selective alcohol and aldehyde dehydrogenases (constitutive, NAD+-dependent), the equilibrium of the alcohol dehydrogenase shifted to reduction of citronellal. Geotrichum candidum JCM 01747 accumulated very high concentrations of citronellic acid (conversion yield 90% in 5 days or accumulation 65 mg/ml in 13 days) in spite of the strong toxicity of the acid, although the optical purity was low. For the alleviation of the toxicity of citronellol and accumulation of toxic citronellic acid, the interface bioreactor is superior to the organic-aqueous two-liquid-phase system (dispersion system).

Macrocyclic compounds as EGFR inhibitors and uses thereof

The invention belongs to the field of pharmaceutical chemistry and relates to a macrocyclic compound serving as EGFR inhibitor and application thereof, in particular to a compound shown in the formula (I) or an isomer thereof. Pharmaceutically acceptable salts, solvates, crystalline or prodrugs, processes for their preparation and include pharmaceutical compositions of these compounds and the use of these compounds or compositions for the treatment EGFR-mediated diseases.

Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- And C-Methylations Fine-Tune Conformation and Properties

Incorporating small modifications to peptidic macrocycles can have a major influence on their properties. For instance, N-methylation has been shown to impact permeability. A better understanding of the relationship between permeability and structure is of key importance as peptidic drugs are often associated with unfavorable pharmacokinetic profiles. Starting from a semipeptidic macrocycle backbone composed of a tripeptide tethered head-to-tail with an alkyl linker, we investigated two small changes: peptide-to-peptoid substitution and various methyl placements on the nonpeptidic linker. Implementing these changes in parallel, we created a collection of 36 compounds. Their permeability was then assessed in parallel artificial membrane permeability assay (PAMPA) and Caco-2 assays. Our results show a systematic improvement in permeability associated with one peptoid position in the cycle, while the influence of methyl substitution varies on a case-by-case basis. Using a combination of molecular dynamics simulations and NMR measurements, we offer hypotheses to explain such behavior.

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.

MACROCYCLIC COMPOUNDS FOR THE TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement factor D or a pharmaceutically acceptable salt or composition thereof are provided. The inhibitors described herein target factor D and inhibit or regulate the complement cascade. The inhibitors of factor D described herein reduce excessive activation of complement.