31502-14-4

Usage

Uses

1. Used in the Food Industry:
trans-2-Nonen-1-ol is used as a flavoring agent for its distinct green, fatty, melon-like aroma with a hint of chicken fat and lard nuance. It is particularly useful in enhancing the taste and aroma of various food products, contributing to a more complex and appealing flavor profile.
2. Used as a Fragrance Ingredient:
Due to its unique aroma, trans-2-Nonen-1-ol can be used as a fragrance ingredient in the perfumery industry. Its green, melon-like scent with a touch of fatty and animalic nuances can be incorporated into various fragrance formulations to create a more natural and complex scent.
3. Used in the Flavor and Fragrance Industry:
trans-2-Nonen-1-ol is used as a key component in the creation of both artificial flavors and fragrances. Its ability to mimic natural aromas found in various plants and food items makes it a valuable addition to the flavorist's and perfumer's toolbox.
4. Used in the Chemical Synthesis Industry:
As an unsaturated nonaromatic alcohol, trans-2-Nonen-1-ol can be utilized as a starting material or intermediate in the synthesis of various chemical compounds, particularly those with applications in the pharmaceutical, agrochemical, and specialty chemical industries.

Preparation

By hydrolysis of the corresponding acetate; the acetate is prepared from 1-bromo-2-nonene and acetic anhydride in acetic acid solution

InChI:InChI=1/C9H18O/c1-2-3-4-5-6-7-8-9-10/h7-8,10H,2-6,9H2,1H3/b8-7-

Upstream product

• 18829-56-6 (E)-2-Nonenal 
• 76853-14-0 2-nonenyl bromide 
• 1577-98-6 (E)-2-nonenoic acid 
• 124-11-8 non-1-ene 
• 5921-73-3 2-nonyn-1-ol 
• 44767-62-6 n-hexylmagnesium chloride 
• 132350-01-7 2-(1-chloro-2-propenyl)-1,3,2-dioxaborinane 
• 88088-17-9 (1-Vinyl-heptylselanyl)-benzene 
• 124931-13-1 (E)-Non-2-enoic acid methoxy-methyl-amide 
• 158504-99-5 2-(1-heptynyl)oxirane 
• 38112-59-3 ethyl (2E)-non-2-enoate 
• 111-25-1 1-bromo-hexane 
• 111-71-7 heptanal 
• 159680-75-8 (E)-1,1-difluoro-2-ethylidenehept-1-yl methanesulfonate 

Downstream Products

• 18829-56-6 (E)-2-Nonenal 
• 2463-53-8 non-2-enal 
• 30418-89-4 (E)-2-nonen-1-ol acetate 
• 40856-16-4 (E)-non-2-enenitrile 
• 317835-30-6 1-Nitro-2-[((E)-non-2-enyl)selanyl]-benzene 
• 857286-62-5 C₂₉H₃₈OSi₂ 
• 852520-79-7 1-{5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methoxymethoxy-undec-1-yn-4-ol 
• 852520-80-0 tert-butyl-[4-{5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-(1-methoxymethoxyheptyl)-but-3-ynyloxy]-dimethylsilane 
• 21964-44-3 non-1-en-3-ol 
• 23433-07-0 (+/-)-1,3-nonanediol 
• 42789-13-9 1,2-Nonanediol 
• 143-08-8 nonyl alcohol 
• 1438414-18-6 C₁₇H₂₅NO₄S 

Relevant academic research and scientific papers

Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes

The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.

Lithium triethylborohydride as catalyst for solvent-free hydroboration of aldehydes and ketones

Commercially available and inexpensive lithium triethylborohydride (LiHBEt3) acts as efficient catalyst for the solvent-free hydroboration of a wide range of aldehydes and ketones, which were subsequently transformed to corresponding 1° and 2° alcohols in one-pot procedure at room temperature (rt).

Asymmetric Cα-Alkylation of Proline via Chirality Transfers of Conformationally Restricted Proline Derivative: Application to the Total Synthesis of (-)-Amathaspiramide F

An efficient strategy for the asymmetric synthesis of Cα-tetrasubstituted proline derivatives from proline has been established. A nitrogen-fused bicyclic system was devised to control the stereodynamics of proline. Through N-quaternizations with allylic electrophiles followed by [2,3]-rearrangements, the bicyclic proline system delivered enantioenriched Cα-tetrasubstituted prolines. This strategy was applied to the concise total synthesis of (-)-amathaspiramide F.

Rhodium-Catalyzed Synthesis of α,β-Unsaturated Ketones through Sequential C-C Coupling and Redox Isomerization

A novel Rh(I)-catalyzed sequential C-C coupling and redox isomerization between allylic alcohols and 1,3-dienes has been accomplished. This versatile protocol provides expeditious access to a broad range of polysubstituted α,β-unsaturated ketones with excellent atom economy and regioselectivity.

Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate

Catalytic enantioselective allyl-allyl cross-coupling of a borylated allylboronate reagent gives versatile borylated chiral 1,5-hexadienes. These compounds may be manipulated in a number of useful ways to give functionalized chiral building blocks for asymmetric synthesis.

Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds

3-Hydroxyhexobarbital dehydrogenase (3HBD) catalyzes NAD(P) +-linked oxidation of 3-hydroxyhexobarbital into 3-oxohexobarbital. The enzyme has been thought to act as a dehydrogenase for xenobiotic alcohols and some hydroxysteroids, but its physiological function remains unknown. We have purified rabbit 3HBD, isolated its cDNA, and examined its specificity for coenzymes and substrates, reaction directionality and tissue distribution. 3HBD is a member (AKR1C29) of the aldo-keto reductase (AKR) superfamily, and exhibited high preference for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D2, which were converted to 3α-, 17β- and 20α-hydroxysteroids and 9α,11β- prostaglandin F2, respectively. Especially, α-diketones (such as isatin and diacetyl) and lipid peroxidation-derived aldehydes (such as 4-oxo- and 4-hydroxy-2-nonenals) were excellent substrates showing low Km values (0.1-5.9 μM). In 3HBD-overexpressed cells, 3-oxohexobarbital and 5β-androstan-3α-ol-17-one were metabolized into 3-hydroxyhexobarbital and 5β-androstane-3α,17β-diol, respectively, but the reverse reactions did not proceed. The overexpression of the enzyme in the cells decreased the cytotoxicity of 4-oxo-2-nonenal. The mRNA for 3HBD was ubiquitously expressed in rabbit tissues. The results suggest that 3HBD is an NADPH-preferring reductase, and plays roles in the metabolisms of steroids, prostaglandin D2, carbohydrates and xenobiotics, as well as a defense system, protecting against reactive carbonyl compounds.

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.

Titanocene-promoted eliminations on epoxy alcohols and epoxy esters

The reaction of a series of 2,3-epoxy alcohols and the corresponding formates, acetates, and benzoates promoted by Cp2TiCl has been studied. The different outcome of the reaction of epoxy derivatives has been rationalized in terms of mechanistically biased processes. After homolytic oxirane cleavage, four main types of reaction were found: dehydroxylation, decarboxylation, dehydrogenation, and deoxygenation. The reaction products varied according to the substitution pattern. The radical nature of these eliminations is demonstrated.

Total synthesis of microcarpalide

An efficient, convergent approach for the total synthesis of microcarpalide (1) is described. The synthetic strategy features the Sharpless asymmetric dihydroxylation, regioselective epoxide opening with various nucleophiles such as a lithium acetylide and cuprates derived from the vinyl stannane and the vinyl iodide for the construction of a C7-C8 trans-double bond and Yamaguchi macrolactonization as the key steps.

Acetyl chloride-ethanol brings about a remarkably efficient conversion of allyl acetates into allyl chlorides

AcCl-EtOH transforms primary and secondary allyl acetates into allyl chlorides that retain the olefinic bond in the more stable position. Whereas secondary allyl alcohols also react with almost the same efficacy as the acetates, the reactions of primary allyl alcohols that possess 1, 2-disubstituted alkenes are very slow. The products are isolated in high state of purity simply by removal of the volatiles.