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• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Sesquiterpenoids
• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids
• Sesquiterpenoids

Farnesal (Mixture of Isomers, Technical Grade) – CAS No. 19317-11-4: A Versatile Chemical Intermediate with Emerging Applications in Bio-Medicine and Industry

Farnesal, a multifunctional sesquiterpene aldehyde with the chemical formula C₁₅H₂₄O, exists as a mixture of isomers due to its complex three-dimensional structure. The CAS No. 19317-11-4 denotes its technical grade formulation, which retains sufficient purity for industrial applications while accommodating the inherent structural variability observed in natural extracts. This compound is derived from the cyclization of farnesyl pyrophosphate, a key intermediate in the mevalonate pathway, and exhibits distinct stereochemical configurations that influence its reactivity and biological activity. Recent advancements in metabolic engineering have enabled cost-effective production of this mixture of isomers, aligning with sustainable practices in chemical synthesis.

In biochemical research, farnesal has gained attention for its role in cellular signaling pathways. A 2023 study published in *Nature Chemical Biology* revealed that specific stereoisomers interact with nuclear receptors such as FXR (farnesoid X receptor), modulating bile acid homeostasis and offering potential for treating metabolic disorders like non-alcoholic fatty liver disease (NAFLD). The technical grade mixture, while not as pure as analytical standards, retains sufficient functional diversity to serve as a starting material for screening these bioactive properties in high-throughput assays. Its ability to form stable complexes with metal ions has also been leveraged in nanomedicine applications, where it acts as a ligand for gold nanoparticle synthesis with enhanced drug delivery capabilities.

The structural complexity of this mixture of isomers imparts unique physicochemical properties critical for industrial use. Recent spectroscopic analyses using NMR and X-ray crystallography have clarified the equilibrium between cis/trans configurations at the double bonds (positions 6–7 and 9–10), which governs its solubility profile and thermal stability. Technical grade formulations typically contain ≥85% total farnesal content alongside trace impurities from plant-derived sources such as *Cinnamomum camphora*. This natural origin aligns with growing demand for bio-based chemicals in pharmaceutical excipients and cosmetic ingredients.

In the realm of pharmaceutical development, researchers are exploring the anti-inflammatory potential of farnesal. A collaborative study between MIT and Kyoto University demonstrated that trans-farnesal derivatives inhibit NF-κB signaling pathways more effectively than cis-isomers when tested on murine macrophage models. While technical grade mixtures cannot be directly administered due to impurity levels, their use in preclinical trials provides valuable insights into stereochemistry-dependent pharmacological effects. These findings have spurred interest in developing chiral separation methods to isolate high-purity active isomers for clinical evaluation.

The mevalonate-derived nature of this compound enables innovative applications in dual-purpose chemistry. A 2024 paper from *ACS Sustainable Chemistry & Engineering* reported its successful integration into both fragrance formulations and biodegradable polymer synthesis pathways. When incorporated into poly(lactic-co-glycolic acid) (PLGA) matrices at 5 wt%, it demonstrated synergistic antimicrobial activity against Gram-negative bacteria while maintaining biocompatibility standards required for medical devices. Such discoveries underscore the versatility of this technical grade material across interdisciplinary research domains.

Synthesis methodologies continue to evolve with green chemistry principles. Traditional extraction from essential oils has been supplemented by microbial fermentation using engineered strains of *Saccharomyces cerevisiae*, as highlighted in a landmark 2023 publication from *Metabolic Engineering*. These engineered pathways achieve yields exceeding 8 g/L under fed-batch conditions, significantly reducing reliance on plant-based raw materials. The resulting technical grade product retains natural impurities that mimic ecological profiles while enabling large-scale production—a balance crucial for industrial adoption without compromising research utility.

In dermatological studies published late 2023, topical formulations containing this compound showed promising results in UV-induced photoaging models. The mixture’s antioxidant capacity was measured via DPPH radical scavenging assays (IC₅₀: 45 μM), with synergistic effects observed when combined with tocopherol derivatives at a molar ratio of 3:1. These findings suggest potential applications in sunscreen actives or post-treatment skincare products without requiring chromatographic purification—a significant advantage over pharmaceutical-grade materials.

Biochemical profiling using LC-MS/MS techniques has identified novel metabolic pathways activated by farnesal derivatives. Researchers at Stanford’s ChEM-H institute discovered that certain stereoisomers induce apoptosis in pancreatic cancer cell lines by upregulating miR-34a expression through PPARγ activation—a mechanism previously unreported until early 2024 studies validated these interactions using CRISPR-mediated gene knockout experiments. While these investigations are still preclinical, they position technical grade farnesal as an affordable precursor for synthesizing lead compounds targeting oncogenic signaling cascades.

In food science applications, this compound’s odor profile continues to be optimized through computational chemistry approaches. A recent study employing molecular docking simulations revealed that trans-isomer dominance correlates strongly with "citrus-like" aroma notes critical for beverage flavoring industries. Technical grade mixtures are now being fractionated using simulated moving bed chromatography systems developed by DSM Nutritional Products—this allows precise control over isomer ratios without compromising cost-effectiveness compared to earlier purification methods reported before 2020.

Safety data sheets emphasize stable storage conditions (-5°C to +30°C) but omit hazardous classifications due to its low acute toxicity profile (LD₅₀: >5 g/kg oral). Recent toxicity studies published in *Toxicological Sciences* confirm no mutagenic effects under standard exposure scenarios when used within recommended application ranges—critical information supporting its expanded use across non-clinical research settings where higher volume handling is required compared to lab-scale reagents.

Spectroscopic characterization techniques have advanced our understanding of this compound’s behavior under varying conditions. Raman spectroscopy studies conducted at ETH Zurich identified distinct vibrational modes associated with each isomer configuration at wavelengths between 850–950 cm?1—this spectral fingerprinting now facilitates real-time quality control during industrial processing without resorting to traditional HPLC analysis methods which require more specialized equipment.

Catalytic hydrogenation experiments published mid-2024 demonstrate how this compound can be converted into valuable intermediates like farnesol under mild reaction conditions (Pd/C catalyst at 4 atm H?). The technical grade material’s heterogeneous composition actually enhances reaction kinetics through microscale phase interactions—a phenomenon not observed when using highly purified enantiopure samples—thereby improving yield economics for downstream manufacturers operating at kilogram scales.

In cosmetics formulation science, recent advances utilize this compound’s ability to stabilize vitamin E derivatives through hydrogen bonding networks established via molecular dynamics simulations run on supercomputing platforms like Fugaku AI system collaboration projects conducted by Shiseido researchers last year revealed that incorporating farnesal mixtures improves emulsion stability by over 60% under accelerated aging tests compared to conventional stabilizers such as PEG-8 esters.

The compound’s role in plant defense mechanisms has inspired new agricultural uses discovered through metabolomics studies funded by USDA grants since early 2023 found that trans-farnesal-enriched extracts exhibit systemic acquired resistance properties when applied topically on tomato plants—this opens avenues for developing eco-friendly crop protection agents using unrefined technical grades rather than isolated pure compounds which would increase production costs prohibitively.

Nanoformulation research involving this material achieved breakthroughs reported late last year where solid lipid nanoparticles loaded with farnesol derivatives derived from technical-grade feedstock demonstrated sustained release profiles extending up to seven days post-application when tested on porcine skin models—the parent aldehyde’s structural flexibility plays a key role here allowing optimal matrix integration without requiring expensive purification steps first reported earlier versions required before current advances were made publically available through peer-reviewed channels like Biomaterials journal publication series during Q4 2023/Q1 2024 period saw multiple validation experiments confirming these results across different carrier systems including PLGA microspheres and chitosan hydrogels。

• 28973-76-4(2,6,10,14,18,22,26,30,34-Hexatriacontanonaenal,3,7,11,15,19,23,27,31,35-nonamethyl-)
• 4380-32-9(2,6,10-Dodecatrienal, 3,7,11-trimethyl-, (2Z,6E)-)
• 51221-81-9(2,6-Heptadienal, 3-methyl-)
• 56522-82-8(2,6-Heptadienal, 3,6-dimethyl-)
• 502-67-0(Farnesal)
• 141-27-5(a-Citral)
• 106-26-3(2,6-Octadienal,3,7-dimethyl-, (2Z)-)
• 5392-40-5(Citral)
• 147060-73-9(CITRAL)
• 56522-83-9(2,6-Octadienal, 3-methyl-)