99814-65-0

Usage

Long-chain unsaturated alcohol

1-Pentadecen-3-ol is an alcohol with a long hydrocarbon chain (15 carbon atoms) and an unsaturated bond, which contributes to its unique properties.

Carbon-carbon double bond at the third position

The double bond in 1-Pentadecen-3-ol is located at the third carbon atom from the omega (end) of the molecule, which influences its chemical reactivity and physical properties.

Naturally occurring compound

1-Pentadecen-3-ol can be found in various natural sources, such as fruits, vegetables, and essential oils, indicating its widespread presence in the environment.

Use in perfumes and flavorings

Due to its pleasant aroma and taste, 1-Pentadecen-3-ol is used in the production of perfumes and flavorings, adding desirable scents and flavors to various products.

Antimicrobial properties

1-Pentadecen-3-ol has potential antimicrobial properties, which means it may be able to inhibit the growth or kill microorganisms, making it a potential candidate for use in pharmaceuticals and other applications.

Antioxidant properties

As an antioxidant, 1-Pentadecen-3-ol may help protect cells from damage caused by free radicals, which could be beneficial in the development of skincare products and other health-related applications.

Upstream product

• 15890-72-9 laurylmagnesium bromide 
• 107-02-8 acrolein 
• 10486-19-8 tridecanal 
• 1826-67-1 vinyl magnesium bromide 
• 150990-67-3 [(2S,3S)-3-dodecyloxiran-2-yl]methanol 
• 143-15-7 1-dodecylbromide 

Downstream Products

• 99814-66-1 (pentadecene-1-yl-3 oxy)-3 methoxy-5 benzoquinone-1,2 
• 150-76-5 4-methoxy-phenol 
• 853947-44-1 1-methoxy-2-(pentadec-1-en-3-yloxy)benzene 
• 929282-76-8 1-{(3S,8aR)-8a-dodecyl-5-methyl-3-phenyl-2,3,8,8a-tetrahydro-7H-[1,3]oxazolo[3,2-a]pyridin-6-yl}ethanone 
• 477946-25-1 (4R,5R)-4-Hydroxy-5-methoxymethoxy-heptadecanoic acid benzylamide 
• 99814-68-3 5-Methoxy-3-pentadecyl-benzene-1,2,4-triol 
• 21551-64-4 2-hydroxy-5-methoxy-3-pentadecyl-1,4-benzoquinone 
• 116138-78-4 hydroxy-2 (pentadecene-2-yl-1)-3 methoxy-5 benzoquinone-1,4 
• 144078-11-5 2-methoxy-6-(pentadecyl)-1,4-benzoquinone 
• 16825-58-4 hydrourushiol monomethyl ether 
• 853947-45-2 2-methoxy-6-(pentadec-2-enyl)phenol 

Relevant academic research and scientific papers

Regioselective Opening of Chiral Hydroxy Epoxides: A Short Route to Muricatacin and its Diastereomer epi-Muricatacin

The dilithioacetate opening of chiral epoxides, obtained by the Sharpless asymmetric epoxidation procedure, led regiospecifically to the corresponding hydroxy γ-lactones thus opening a short route to epimuracatacin and muricatacin.

Synthesis of cis-Solamin using a permanganate-mediated oxidative cyclization

(graph presented) cis-Solamin (1) and its diastereoisomer 14 have been synthesized in 13 steps using the diastereoselective permanganate-promoted oxidative cyclization of 1,5-dienes to create the tetrahydrofuran diol core. Notably, no protecting groups are required during the stages of fragment assembly.

Asymmetric synthesis of both enantiomers of a δ-lactone analogue of muricatacin

The asymmetric synthesis of both enantiomers of the δ-lactone analogue of the antitumoral natural product γ-lactone muricatacin has been carried out. Initial attempts to also synthesize the natural product proved unsuccessful due to the poor reactivity of the Grignard reagent derived from 2-(bromomethyl)-1,3-dioxolane. The designed synthetic route enabled us to increase the ring size to generate the δ-lactone analogue employing Sharpless asymmetric epoxidation and ZrCl4-catalyzed intramolecular acetalization as the key steps. Georg Thieme Verlag Stuttgart.New York.

Microwave-mediated claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring 1,4-benzoquinones. The first syntheses of verapliquinones A and B and panicein A

The naturally occurring 1,4-benzoquinones 2-methoxy-6-propyl-1,4- benzoquinone (1), 2-methoxy-6-pentyl-1,4-benzoquinone (primin 2), 2-methoxy-6-pentadecyl-1,4-benzoquinone (3), 2-methoxy-6-heptadecyl-l,4- benzoquinone (dihydroirisquinone, pallasone B; 4) were synthesized by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 10, followed by hydrogenation of the side chain alkene, and oxidation to the quinone. The Claisen-based methodology was extended to the first synthesis of the marine benzoquinones verapliquinones A and B (5 and 6), and panicein A (7). Isoarnebifuranone (9) was also synthesized by a similar strategy.

Synthesis of two possible diastereomers of reticulatain-1

A convergent synthesis of two possible diastereomers of reticulatain-1 (1a and 1b) was accomplished. Comparison of the specific optical rotations of 1a and 1b did not allow for the strict determination of the absolute configuration. However, bis-(R)-MTPA

Syntheses of (4R,5S)- and (4S,5R)-muricatacins, and (4S,5R)-aza-muricatacin, unnatural analogues of the annonaceous acetogenin

(4R,5S)- and (4S,5R)-Muricatacins, and (4S,5R)-aza-muricatacin, unnatural analogues of the Annonaceous acetogenin, were prepared from (-)-muricatacin via Mitsunobu inversion or Weinreb amidation as the key step.

Stereoselective synthesis of a versatile intermediate for the total synthesis of mono- and bis-THF containing annonaceous acetogenins

Stereoselective synthesis of epoxy tetrahydrofuran (THF) 1, a versatile synthetic precursor for mono-THF and bis-THF containing annonaceous acetogenins, is reported. Compound 1 was synthesized from tridecanal in 11 steps with an overall yield of 24%. The

1,3-Transposition of primary allylic alcohols: Synthesis of optically active secondary and tertiary allylic alcohols

The reduction of optically active 2,3-epoxy alcohols, suitably prepared by the Sharpless asymmetric epoxidation of primary allylic alcohols, with the system triphenylphosphine/ iodine/imidozole/2,6-lutidine/water, leads in a single step to optically active secondary and tertiary allylic alcohols.

A general approach to γ-lactones via osmium-catalyzed asymmetric dihydroxylation. Synthesis of (-)- and (+)-muricatacin

Both enantiomers of hydroxy γ-lactones have been prepared highly enantioselectively (92-99% ee) using either AD-mix-β or AD-mix-α with both β,γ- and γ,δ-unsaturated esters. The method is exemplified by the three-step synthesis of (-) and (+)-muricatacin i

A Convenient Synthesis of the Peach Fruit Moth Carposina Niponensis Walk. and of the Douglas Fir Tussock Moth Orgya Pseudotsugata Mc.D. Sex Pheromones and Analogs

The (Z)- and (E)-isomers of 7-alken-11-ones with chain lengths of 19, 21 and 23 carbon atoms were synthesized.A procedure based on the reaction of alkenylcopper reagents with vinylketones has been elaborated.