40642-43-1

Basic information

• Product Name: CIS-7-TETRADECENOL
• Synonyms: CIS-7-TETRADECENOL;(7Z)-7-Tetradecen-1-ol;(Z)7-Tetradecen-1-ol;7-Tetradecen-1-ol, (Z);cis-7-Tetradecen-1-ol;Z-7-Tetradecenol;(Z)-7-TDOL;Z-7-TDOL
• CAS NO: 40642-43-1
• Molecular Formula: C₁₄H₂₈O
• Molecular Weight: 212.37152
• Mol File: 40642-43-1.mol

Chemical Properties

• Boiling Point: 305.3°C at 760 mmHg
• Flash Point: 61 °C
• Appearance: /
• Density: 0.846g/cm³
• Vapor Pressure: 7.8E-05mmHg at 25°C
• Refractive Index: 1.458
• Storage Temp.: 2-8°C
• Solubility: Acetone, Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: CIS-7-TETRADECENOL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-7-TETRADECENOL(40642-43-1)
• EPA Substance Registry System: CIS-7-TETRADECENOL(40642-43-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 40642-43-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CIS-7-TETRADECENOL is used as an intermediate in the synthesis of (4E, 11Z)-Sphingadienine-C18-1-phosphate, which is a sphingoid base of sea cucumber cerebroside. CIS-7-TETRADECENOL has shown potential cytotoxicity activity against human colon cancer cells, making it a promising candidate for the development of novel anticancer drugs.
Used in Chemical Synthesis:
CIS-7-TETRADECENOL can be utilized as a key intermediate in the synthesis of various complex organic compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its unique structural features, including the presence of a double bond, make it a valuable building block for the development of new molecules with diverse biological activities.

InChI:InChI=1/C14H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h7-8,15H,2-6,9-14H2,1H3/b8-7-

Upstream product

• 111-71-7 heptanal 
• 76771-95-4 7-hydroxy-heptyl-triphenyl-phosphonium bromide 
• 37011-94-2 7-tetradecyne-1-ol 
• 629-05-0 n-octyne 
• 60579-52-4 1-chloro-1-boracycloheptane 
• 22054-13-3 7-hydroxyheptanal 
• 55367-56-1 n-heptylidene triphenylphosphorane 
• 37043-40-6 2-(tetradec-7-yn-1-yloxy)tetrahydro-2H-pyran 
• 533-87-9 threo-9,10,16-trihydroxyhexadecanoic acid 
• 3990-05-4 ethyl 6-formylhexanoate 
• 92169-43-2 ethyl 7,7-diethoxyheptanoate 
• 13423-48-8 triphenylheptylphosphonium bromide 
• 82670-30-2 E-5,5-diethoxy-2-pentenal 
• 125043-76-7 erythro-1,7,8-triacetoxy-14-pentadecene 

Downstream Products

• 65128-96-3 (Z)-7-tetradecenal 
• 16974-10-0 1-acetoxy-(Z)-7-tetradecene 
• 2430-95-7 (Z)-tetradec-7-enoic acid 
• 83005-39-4 sec-butyl (Z)-7-tetradecenoate 
• 1352404-14-8 (7R,8S)-methyl 7,8-bis((S)-2-methoxy-2-phenylacetoxy)tetradecanoate 
• 1352404-40-0 (7S,8R)-methyl 7,8-bis((S)-2-methoxy-2-phenylacetoxy)tetradecanoate 
• 76963-23-0 3-oxo-(Z)-9-hexadecenal 
• 592543-41-4 2-(4-methoxybenzyloxy)ethyl 2-deoxy-2-(2,2-difluorotetradecanamido)-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-α-D-glycopyranoside 
• 592543-40-3 2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside 

Relevant articles and documents

Method for synthesizing cis-7-tetradecenol acetate which is main component of sex pheromone of holcocerus vicarius walker

The invention discloses a method for synthesizing cis-7- tetradecenol acetate which is a main component of sex pheromone of holcocerus vicarius walker. The method includes (1), preparing (7-bromo-heptyl-1-)-2-tetrahydropyran ether; (2), preparing (7-bromo

Simple syntheses of (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate from aleuritic acid

Insect sex pheromones are used for monitoring and management of crop pests. Four compounds (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate reported as components of some important agricultural insect pests have been synthesized from theo-aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) involving simplified Wittig reactions with improved yield.

Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: Substrate precursors for cytochrome P450BioI

A series of highly enantioenriched hydroxy- and dihydroxy-fatty esters were required as part of our ongoing investigation into cytochrome P450 BioI. This mediates the biosynthesis of pimelic acid via C-C bond cleavage of long chain fatty acids within Bacillus subtilis. Herein we report the synthesis of various stereoisomers of methyl 7-hydroxytetradecanoate, methyl 8-hydroxytetradecanoate, and methyl 7,8-dihydroxytetradecanoate in highly enantioenriched form, using a combination of asymmetric synthesis and a preparative enantioselective HPLC is reported.

Synthesis of carboxymethyl GLA-60 ether derivatives containing an olefin in their chains and their LPS-antagonistic activities

Anomeric carboxymethyl GLA-60 olefine derivatives having ether chains instead of ester chains in their side chains were synthesized and their biological activities toward both human U937 cells and mouse PEC-macrophage cells were measured. The species-specific behavior of these compounds in humans (LPS-antagonistic) and mice (very weak LPS-antagonistic, but almost inactive) found this time was different from that in humans (LPS-antagonistic) and mice (endotoxic) found in the biosynthetic precursor of lipid A, such as lipid IVa. However, this fact also shows, interestingly enough, that a difference exists in the molecular recognition between human and mouse LPS receptors.

B-5354a, b and c, new sphingosine kinase inhibitors, produced by a marine bacterium; taxonomy, fermentation, isolation, physico-chemical properties and structure determination

In the course of our screening for inhibitors of sphingosine kinase, we found a series of active compounds in a culture broth of a novel marine bacterium, SANK 71896. The structures of the compounds, named B-5354a, b and c, were elucidated by a combination of spectroscopic analyses to be new esters of 4-amino-3-hydroxybenzoic acid with long-chain unsaturated alcohols. B-5354a, b and c inhibit sphingosine kinase activity with IC50 values of 21, 58 and 38 υM, respectively.

Sex pheromone of female vine bud moth, Theresimima ampellophaga comprises (2s)-butyl (7z)-tetradecenoate

The sex pheromone of the vine bud moth, Theresimima ampellophaga, released at the 3rd-5th abdominal tergites, was identified by coupled GC-EAG, GC-MS, and synthesis as (2S)-butyl (7Z)-tetradecenoate. For the first time, full stereochemistry is unambiguously defined for the sex pheromone of a member of the Zygaenidae. The synthetic compound caught significant numbers of males in field-trapping experiments.

SYNTHESIS OF (Z)-7-TETRADECENYL ACETATE AND SEC.BUTYL (Z)-7-TETRADECENOATE FROM ALEURITIC ACID.

Aleuritic acid (3), after acetylation, was oxidatively decarboxylated and then phase transfer oxidation of the terminal olefin gave 7,8,14-trihydroxytetradecanoic acid.Simple conventional methods led to the synthesis of titled pheromones.

Pheromones via Organoboranes. 3. Vinylic Organoboranes. 10. Stereospecific Synthesis of (Z)- and (E)-6- and -7-Alken-1-ols via Boracyclanes

Treatment of B-(E)-1-alkenylborinanes, obtained via monohydroboration of 1-alkynes with borinane, with iodine in the presence of a base results in the migration of one end of the cycloalkyl chain from boron to the adjacent carbon, producing intermediates containing the seven-membered borepane moiety, which undergo rapid deiodoboronation to afford the (Z)-6-alkenyl-1-boronate esters.These boronate esters, upon oxidation, provide (Z)-6-alken-1-ols.The procedure is successfully extended to B-(E)-7-alkenylborepane derivatives to produce (Z)-7-alken-1-ols.The preparationof (E)-6- and -7-alken-1-ols has been carried out via borinane and borepane derivatives.Borinane, as prepared previously, hydroborates cleanly 1-bromo-1-alkynes to provide the B-((Z)-1-bromo-1-alkenyl)borinanes.Treatment of these boron intermediates with sodium methoxide results in the displacement of bromine by one end of the boracycloalkyl moiety, producing the corresponding vinylboranes containing the seven-membered borepane moiety.The intermediates, upon controlled protonolysis, followed by oxidation, afford the (E)-6-alken-1-ols.The methodology was extended to borepane derivatives to provide (E)-7-alken-1-ols.The above procedures constitute a simple, very convenient, stereospecific, and general one-pot synthesis of (Z)- and (E)-6- and -7-alken-1-ols.The methodology has been applied to the synthesis of representative pheromones containing a (Z)- or an (E)-alkene moiety in good yields.