2541-61-9

Usage

Uses

Used in Flavor and Fragrance Industry:
(9Z,12Z)-9,12-Octadecadienal is used as a flavoring and fragrance agent in the food and fragrance industries due to its strong, pleasant odor.
Used in Health and Medicine:
(9Z,12Z)-9,12-Octadecadienal is studied for its potential health benefits, including its anti-inflammatory and anti-cancer properties, indicating its potential use as a therapeutic agent in the field of health and medicine.

InChI:InChI=1/C18H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h6-7,9-10,18H,2-5,8,11-17H2,1H3

Upstream product

• 2501-33-9 N,N-dimethyllinoleamide 
• 544-35-4 ethyl (9Z,12Z)-9,12-octadecadienoate 
• 29204-20-4 10Z,13Z-nonadecadienoic acid 
• 72297-07-5 <(3Z)-nonen-1-yl>triphenylphosphonium iodide 
• 81965-50-6 10-(tetrahydropyran-2'-yloxy)decanal 
• 79-37-8 oxalyl dichloride 
• 506-43-4 Linoleyl alcohol 
• 7619-08-1 octadeca-9,12-dienoic acid ethyl ester 
• 112-63-0 Methyl linoleate 
• 60-33-3 linoleic acid 
• 7459-33-8 linoleyl chloride 
• 66855-81-0 (10Z,13Z)-Nonadeca-10,13-dien-1-ol 

Downstream Products

• 107580-81-4 (Z,Z)-4-(7,10-hexadecadienyl)-5-hydroxy-2(5H)-furanone 

Relevant academic research and scientific papers

Continuous-Flow Synthesis of Cationic Lipid SST-01 via Safe and Scalable Aerobic Oxidation and Reductive Amination

The synthesis of the cationic lipid SST-01, a key component of Kyowa Kirin's siRNA-lipid nanoparticles, through a two-step homogeneous continuous-flow process is described. Safe and scalable aerobic oxidation with a catalytic CuI/TEMPO system and diluted oxygen (5% O2 in N2) was utilized in the first step to provide a lipid aldehyde. Subsequent reductive amination of the first-step eluent with methylamine using tetramethylammonium triacetoxyborohydride provided the target SST-01 in an overall yield of 95%.

Cascade Benzannulation Approach for the Syntheses of Lipocarbazoles, Carbazomycins, and Related Alkaloids

Herein, a state-of-the-art one-pot cascade benzannulation technique for the efficacious synthesis of valuable 3-hydroxy-2-methyl carbazoles, a linchpin of more than 25 carbazole-based alkaloids, is unveiled from readily affordable fundamental commodities. The key step of this strategy is gaining aromaticity by site-selective elimination of hydroxyl group controlled by nucleophilicity of the indole ring. The present strategy shows excellent functional group tolerance with a broad substrate scope. The utility of this convenient approach was appealingly exemplified via concise total syntheses of 10 carbazole-based alkaloids possessing significant biological activities and thus of medicinal importance.

Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones

Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.

CATIONIC LIPIDS FOR NUCLEIC ACID DELIVERY AND PREPARATION THEREOF

The present invention provides cationic lipids and lipid nanoparticle formulations comprising these lipids, alone or in combination with other lipids. These lipid nanoparticles may be formulated with nucleic acids to facilitate their intracellular delivery both in vitro and for therapeutic applications. The present invention also provides methods of chemical synthesis of these lipids, lipid nanoparticle preparation and formulation with nucleic acids.

Selective Hydrosilylation of Esters to Aldehydes Catalysed by Iridium(III) Metallacycles through Trapping of Transient Silyl Cations

The combination of an iridium(III) metallacycle and 1,3,5-trimethoxybenzene catalyses rapidly and selectively the reduction of esters to aldehydes at room temperature with high yields through hydrosilylation followed by hydrolysis. The ester reduction involves the trapping of transient silyl cations by the 1,3,5-trimethoxybenzene co-catalyst, supposedly by formation of an arenium intermediate whose role was addressed by DFT calculations.

ALKENYL SUBSTITUTED 2,5-PIPERAZINEDIONES AND THEIR USE IN COMPOSITIONS FOR DELIVERING AN AGENT TO A SUBJECT OR CELL

Provided herein are compounds of Formula (I), and salts thereof, wherein each instance of RL is independently optionally substituted C6-C40 alkenyl. Further provided are compositions comprising a compound of Formula (I) and an agent. Further provided are methods and kits using the compositions for delivering an agent to a subject or cell and for treating and/or preventing a range of diseases. Further provided are methods of preparing compounds of Formula (I) and precursors thereof.

Design and synthesis of protein kinase C epsilon selective diacylglycerol lactones (DAG-lactones)

DAG-lactones afford a synthetically accessible, high affinity platform for probing structure activity relationships at the C1 regulatory domain of protein kinase C (PKC). Given the central role of PKC isoforms in cellular signaling, along with their differential biological activities, a critical objective is the design of isoform selective ligands. Here, we report the synthesis of a series of DAG-lactones varying in their side chains, with a particular focus on linoleic acid derivatives. We evaluated their selectivity for PKC epsilon versus PKC alpha both under standard lipid conditions (100% phosphatidylserine, PS) as well as in the presence of a nuclear membrane mimetic lipid mixture (NML). We find that selectivity for PKC epsilon versus PKC alpha tended to be enhanced in the presence of the nuclear membrane mimetic lipid mixture and, for our lead compound, report a selectivity of 32-fold.

Exploring the synthetic applicability of a new carboxylic acid reductase from Segniliparus rotundus DSM 44985

A new carboxylic acid reductase (CAR) gene from Segniliparus rotundus DSM 44985 was overexpressed in Escherichia coli. The recombinant enzyme exhibited high activity toward a variety of aromatic and aliphatic carboxylic acids. Especially, it effectively reduced 4-hydroxybenzoic acid (8a) and 4-nitrobenzoic acid (19a), toward which the known Nocardia CAR exhibited no or little activity. The recombinant E. coli cells co-expressing the Segniliparus CAR and Nocardia PPTase genes catalyzed the reductions of vanillic acid (20a) and 3,4-dihydroxyphenylacetic acid (25a) to give vanillyl alcohol (20c) and 3-hydroxytyrosol (25c) with high yield, respectively. The endogenous aldehyde reductases of E. coli should be responsible for the further reduction of the produced aldehydes. These results demonstrated that Segniliparus CAR was a useful addition to the biocatalyst tool-box for the reduction of carboxylic acids and might find applications in the synthesis of valuable bio-based chemicals from renewable resources.

NOVEL TRIALKYL CATIONIC LIPIDS AND METHODS OF USE THEREOF

The present invention provides compositions and methods for the delivery of therapeutic agents to cells. In particular, these include novel cationic lipids and nucleic acid-lipid particles that provide efficient encapsulation of nucleic acids and efficient delivery of the encapsulated nucleic acid to cells in vivo. The compositions of the present invention are highly potent, thereby allowing effective knock-down of a specific target protein at relatively low doses. In addition, the compositions and methods of the present invention are less toxic and provide a greater therapeutic index compared to compositions and methods previously known in the art.

SPECIFICITY OF THE ENZYME SYSTEM PRODUCING LONG CHAIN ALDEHYDES IN THE GREEN ALGA, ULVA PERTUSA

The greater part of the enzyme activity producing long chain aldehydes (LCA) such as (8Z)-heptadecanal, (8Z,11Z)-heptadecadienal, (8Z,11Z,14Z)-heptadecatrienal was found in the 4000 g precipitate of homogenates of the green alga, Ulva pertusa.The LCA-forming activity was readily solubilized from the precipitate by addition of 0.2percent Triton X-100.The solubilized LCA-forming activity showed an optimum pH in the range 8.5-9.5. α-Linolenic acid was a very good substrate, but γ-linolenic acid was a poor substrate for the activity.Linoleic acid was the best substrate of an entire series of (ζ6Z, ζ9Z)-dienoic acids, in which the chain length varied from C13 to C20.Key Word Index - Ulva pertusa; green alga; odour; aldehydes; fatty acids; substrate specificity.