55182-74-6

Basic information

• Product Name: 3-TETRADECYN-1-OL
• Synonyms: 3-TETRADECYN-1-OL;TIMTEC-BB SBB008956
• CAS NO: 55182-74-6
• Molecular Formula: C₁₄H₂₆O
• Molecular Weight: 210.36
• Mol File: 55182-74-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 32.5°C (estimate)
• Boiling Point: 155-156°C 0,8mm
• Flash Point: 155-156°C/0.8mm
• Appearance: /
• Density: 0.8070 (estimate)
• Vapor Pressure: 2.22E-05mmHg at 25°C
• Refractive Index: 1.4620
• PKA: 14.33±0.10(Predicted)
• BRN: 2079395
• CAS DataBase Reference: 3-TETRADECYN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-TETRADECYN-1-OL(55182-74-6)
• EPA Substance Registry System: 3-TETRADECYN-1-OL(55182-74-6)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 55182-74-6(Hazardous Substances Data)

Usage

General Description

3-Tetradecyn-1-ol is a chemical compound with the molecular formula C14H26O. It is an unsaturated alcohol with a long carbon chain and a triple bond between the third and fourth carbon atoms. 3-Tetradecyn-1-ol is commonly used in organic synthesis and as a starting material for the production of various derivatives. It is also a known pheromone component in insect species, playing a role in communication and mating behavior. 3-Tetradecyn-1-ol has been investigated for its potential biological activities, such as antibacterial and antifungal properties, and has the potential for applications in the development of pharmaceuticals and agricultural products.

InChI:InChI=1/C14H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h15H,2-10,13-14H2,1H3

Upstream product

• 75-21-8 oxirane 
• 765-03-7 1-dodecyne 
• 112-29-8 1-bromo dodecane 
• 927-74-2 3-Butyn-1-ol 

Downstream Products

• 54897-65-3 (Z)-3-Tetradecen-1-ol acetate 
• 68892-27-3 (Z)-Tetradec-3-en-1-ol 
• 1363408-14-3 C₂₄H₃₂O₃ 
• 139100-88-2 1,2-(13,15-octacosadiyne-1,28-dioyl)-3-(4-methoxybenzyl)-sn-glycerol 
• 139100-85-9 1,2-di-13-tetradecyn-1-oyl-3-(4-methoxybenzyl)-sn-glycerol 
• 139100-94-0 2-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol 
• 82909-47-5 13-Tetradecyn-1-oic acid 
• 68900-86-7 trans-3-tetradecen-1-ol 
• 18202-12-5 14-hydroxy-1-tetradecyne 
• 144368-12-7 2',5-anhydro-6-deoxy-1,2-O-isopropylidene-6-C-[3'R-benzoyloxy-2'R-hydroxy-tridecyl]-β-L-idofuranose 
• 144489-84-9 2',5-anhydro-6-deoxy-1,2-O-isopropylidene-6-C-[3'S-benzoyloxy-2'S-hydroxy-tridecyl]-β-L-idofuranose 
• 144489-81-6 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-(tridec-2'-ynyl)-β-L-idofuranose 
• 144368-08-1 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-(tridec-2'-ynyl)-α-D-glucofuranose 
• 144368-11-6 Benzoic acid (S)-1-[(2S,5R)-5-((3aS,5S,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-yl]-undecyl ester 

Relevant articles and documents

Natural trienoic acids as anticancer agents: First stereoselective synthesis, cell cycle analysis, induction of apoptosis, cell signaling and mitochondrial targeting studies

The first Z-stereoselective method was developed for the synthesis of unsaturated acids containing a 1Z,5Z,9Z-triene moiety in 61–64% yields using the new Ti-catalyzed cross-coupling of oxygen-containing and aliphatic 1,2-dienes as the key synthetic step. It was shown for the first time that trienoic acids with non-methylene-interrupted Z-double bonds show moderate cytotoxic activities against tumor cell lines (Jurkat, K562, U937, HL60, HeLa), human embryonic kidney cells (Hek293), normal fibroblasts and human topoisomerase I (hTop1) inhibitory activity in vitro. The synthesized acids efficiently initiate apoptosis of Jurkat tumor cells, with the cell death mechanism being activated by the mitochondrial pathway. A probable mechanism of topoisomerase I inhibition was also hypothesized on the basis of in silico studies resorting to docking. The activation and inhibition of the most versatile intracellular signaling pathways (CREB, JNK, NFkB, p38, ERK1/2, Akt, p70S6K, STAT3 and STAT5 tyrosine kinases) responsible for cell proliferation and for initiation of apoptosis were studied by multiplex assay technology (Luminex xMAP).

Synthesis of Bis-THF Compounds from D-Glucose

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Syntheses of Monounsaturated Sex Pheromones of Lepidoptera via 3-Alkyn-1-ols

3-Alkyn-1-ols as intermediate synthons in the preparation of some Lepidoteran sex pheromones were utilized.Characteristic fragmentations reflecting the position of the triple bond were found in the mass spectra of 3-alkyn-1-ols and alkyn-1-yl acetates in contrast to 1-tert-butoxy-alkynes.A partial isomerization of 1-tosyloxy-3-(Z)-octene to 1-bromo-3-(E)-octene within the reaction with NaBr in DMF was noticed by GC and 13C-n.m.r., for which a mechanism involving homoconjugation in an intermediate non-classical carbonium ion was suggested.