64461-99-0

Basic information

• Product Name: 2-Tetradecenal
• Synonyms: 2-Tetradecenal;(E)-tetradec-2-enal
• CAS NO: 64461-99-0
• Molecular Formula: C14H26 O
• Molecular Weight: 210.36
• Mol File: 64461-99-0.mol

Chemical Properties

• Melting Point: 15°C (estimate)
• Boiling Point: 299.9°C (estimate)
• Flash Point: 144.4°C
• Appearance: /
• Density: 0.8534 (estimate)
• Vapor Pressure: 0.00121mmHg at 25°C
• Refractive Index: 1.4577 (estimate)
• CAS DataBase Reference: 2-Tetradecenal(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Tetradecenal(64461-99-0)
• EPA Substance Registry System: 2-Tetradecenal(64461-99-0)

Safety Data

• Hazardous Substances Data: 64461-99-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h12-14H,2-11H2,1H3/b13-12+

Upstream product

• 101882-12-6 tetradec-2c-enal-diethylacetal 
• 51534-32-8 1t,3-bis-methylsulfanyl-tetradec-1-ene 
• 7664-93-9 sulfuric acid 
• 112-16-3 n-dodecanoyl chloride 
• 693-67-4 bromoundecane 
• 100904-98-1 [2-(2-Methoxy-ethoxymethoxy)-1-undecyl-cyclopropanesulfonyl]-benzene 
• 18697-01-3 1,1-diethoxy-tetradec-2-yne 
• 74962-98-4 trans-2-tridecenol 
• 112-54-9 Dodecanal 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 75039-86-0 (E)-Tetradec-2-en-1-ol 
• 38112-60-6 (E)-ethyl tetradec-2-enoate 
• 100905-08-6 2-Benzenesulfonyl-2-undecyl-cyclopropanol 

Downstream Products

• 85769-28-4 α-triticene 

Relevant articles and documents

Design, Synthesis, and Activity Evaluation of Novel Acyclic Nucleosides as Potential Anticancer Agents in Vitro and in Vivo

In the present work, 103 novel acyclic nucleosides were designed, synthesized, and evaluated for their anticancer activities in vitro and in vivo. The structure-activity relationship (SAR) studies revealed that most target compounds inhibited the growth of colon cancer cells in vitro, of which 3-(6-chloro-9H-purin-9-yl)dodecan-1-ol (9b) exhibited the most potent effect against the HCT-116 and SW480 cells with IC50 values of 0.89 and 1.15 μM, respectively. Furthermore, all of the (R)-configured acyclic nucleoside derivatives displayed more potent anticancer activity compared to their (S)-counterparts. Mechanistic studies revealed that compound 9b triggered apoptosis in the cancer cell lines via depolarization of the mitochondrial membrane and effectively inhibited colony formation. Importantly, compound 9b inhibited the growth of the SW480 xenograft in a mouse model with low systemic toxicity. These results indicated that acyclic nucleoside compounds are viable as potent and effective anticancer agents, and compound 9b may serve as a promising lead compound that merits further attention in future anticancer drug discovery.

Catalytic Regioselective γ-Methylenation of α,β-Unsaturated Aldehydes Using Formaldehyde via Vinylogous Aldol Condensation

The first vinylogous aldol condensation of α,β-unsaturated aldehydes using aqueous formaldehyde is developed under mild reaction conditions to form the γ-methylenated products with excellent regioselectivity. Using this methodology, a short synthesis of α-triticene, an antifungal compound, is achieved in two steps. The practicality of this methodology is demonstrated by the gram-scale synthesis. Formation of the unusual double γ-functionalized products from crotonaldehyde and a direct asymmetric vinylogous aldol product from phenylglyoxal is also described.

Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases

Bacterial luciferase catalyzes the monooxygenation of long-chain aldehydes such as tetradecanal to the corresponding acid accompanied by light emission with a maximum at 490?nm. In this study even numbered aldehydes with eight, ten, twelve and fourteen carbon atoms were compared with analogs having a double bond at the α,β-position. These α,β-unsaturated aldehydes were synthesized in three steps and were examined as potential substrates in vitro. The luciferase of Photobacterium leiognathi was found to convert these analogs and showed a reduced but significant bioluminescence activity compared to tetradecanal. This study showed the trend that aldehydes, both saturated and unsaturated, with longer chain lengths had higher activity in terms of bioluminescence than shorter chain lengths. The maximal light intensity of (E)-tetradec-2-enal was approximately half with luciferase of P. leiognathi, compared to tetradecanal. Luciferases of Vibrio harveyi and Aliivibrio fisheri accepted these newly synthesized substrates but light emission dropped drastically compared to saturated aldehydes. The onset and the decay rate of bioluminescence were much slower, when using unsaturated substrates, indicating a kinetic effect. As a result the duration of the light emission is doubled. These results suggest that the substrate scope of bacterial luciferases is broader than previously reported.

Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl- 4(1H)-quinolones

A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships.

Structure-Activity relationship of aliphatic compounds for nematicidal activity against pine wood nematode (Bursaphelenchus xylophilus)

Nematicidal activity of aliphatic compounds was tested to determine a structure-activity relationship. There was a significant difference in nematicidal activity among functional groups. In a test with alkanols and 2E-alkenols, compounds with C8-C11 chain length showed 100% nematicidal activity against pine wood nematode, Bursaphelenchus xylophilus, at 0.5 mg/mL concentration. C6-C10 2E-alkenals exhibited >95% nematicidal activity, but the other compounds with C 11-C14 chain length showed weak activity. Nematicidal activity of alkyl acetates with C7-C11 chain length was strong. Compounds belonging to hydrocarbons, alkanals, and alkanoic acetates showed weak activity at 0.5 mg/mL concentration. Nematicidal activity of active compounds was determined at lower concentrations. At 0.25 mg/mL concentration, whole compounds except C8 alkanol, C8 2E-alkenol, and C7 alkanoic acid showed >80% nematicidal activity. C 9-C11 alkanols, C10-C11 2E-alkenols, C8-C9 2E-alkenals, and C9-C10 alkanoic acids showed >80% nematicidal activity at 0.125 mg/mL concentration. Only C11 alkanol exhibited strong nematicidal activity at 0.0625 mg/mL concentration, the lowest concentration that was tested. 2010 American Chemical Society.

Conversion of bromoalkenes into alkynes by wet tetra-n-butylammonium fluoride

(Chemical Equation Presented) Tetra-n-butylammonium fluoride was found to be a mild and efficient base for the elimination reaction of bromoalkenes. Treatment of 1,1-dibromoalkenes, (Z)-1-bromoalkenes, and internal bromoalkenes with 5 equiv of TBAF·3H2O in DMF yielded terminal and internal alkynes in high yields without undue regard to the presence of water.

Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: An efficient method for vinylogation of aromatic aldehydes

Aldehydes were efficiently transformed into allylic dioxolanes by a Wittig-type reaction, using 1,3-dioxolan-2-yl-methyltriphenylphosphonium bromide under phase transfer conditions. The substituent kinetic effects were studied, and related to Hammett values and electrochemical potentials.

Spicamycin derivatives and their use as anticancer agents

Spicamycin derivative represented by the formula (I) or a salt thereof: STR1 wherein R represents specific diverse substituents, for example, a linear alkadienyl having from 11 to 13 carbon atoms, and R1 and R2 respectively represent H or OH. Examples of specific compounds are 6-[4'-N-(N'-trans,trans 2,4-tridecadienoylglycyl)spicaminyl-amino]purine, and 6-[4'-N-(N'-trans,trans-2,4 dodecadienyoly glycyl) spicaminyl-amino]purine. Comopunds according to this invention are useful as a pharmaceutical for inhibition of a tumor, for example, human colon cancer.

A simple and inexpensive synthesis of 2-alkenals

A simple and inexpensive method for the C2 homologation of aldehydes and ketone to 2-alkenals consists of the reaction with allylmagnesium bromide, O-acylation of the resultant 1-alken-4-ol, and ozonolysis.

STABLE CARBON-YLIDES

5-Acylmethylene-1,2,4-triazolium salts were synthesized and converted to stable anhydrobases by aqueous alkali.The close analogy of their spectra with those of phosphorus-ylides and their reactions suggest that the anhydrobases may be regarded as carbon-ylides. α,β-Unsaturated aldehydes were synthesized in moderate yield by selective reduction of the salts folloved by acid hydrolysis.