616-25-1

Usage

Uses

1. Used in Flavor and Fragrance Industry:
1-Penten-3-ol is used as a nature identical flavor and fragrance agent for adding cucumber, melon, berry, horseradish, strawberry, and tomato flavor to foods and beverages.
2. Used in Food Industry:
1-Penten-3-ol is a food additive and can be found in banana oil essence. It is used to enhance the taste and aroma of various foods and beverages, contributing to their green vegetable and fruity taste characteristics at 15 ppm.
3. Occurrence in Foods and Beverages:
1-Penten-3-ol is reported to be found in over 100 foods and beverages, including orange, strawberry, banana, orange peel oil, raspberry, raw asparagus, shallot, crispbread, smoked fatty fish, red wine, black tea, partially fermented tea, green tea, roasted peanut, soybean, scallop, tomato, apricot, tangerine juice, bilberry, other berries, guava, melon, papaya, cabbage, kohlrabi, peas, cooked potato, ginger, tomato, spearmint oil, Scotch spearmint oil, mustard, wheat and rye bread, parmesan cheese, boiled egg, cooked fish, fish oil, roasted chicken, cooked beef, pork fat, hop oil, beer, olive, beans, mango, starfruit, dill herb, lovage leaf, laurel, malt, kiwifruit, endive, shrimp, oyster, nectarine, okra, clam, cape gooseberry, and maté.

References

[1] http://foodb.ca/compounds/FDB008240 [2] George A. Burdock (2016) Fenaroli's Handbook of Flavor Ingredients, Sixth Edition.

Preparation

By prolonged contact of 1-chloro-2-pentene with NaOH solution.

InChI:InChI=1/C5H10O/c1-3-5(6)4-2/h3,5-6H,1,4H2,2H3/t5-/m1/s1

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 56-23-5 tetrachloromethane 
• 10500-11-5 rac-pent-1-en-3-yl acetate 
• 24356-00-1 3-chloro-1-pentene 
• 4016-15-3 2,3-epoxypentane 
• 930-22-3 epoxybutene 
• 15681-48-8 lithium dimethylcuprate * lithium iodide 
• 598-18-5 2-bromopropanol 
• 3536-96-7 vinylmagnesium chloride 
• 1826-67-1 vinyl magnesium bromide 
• 123-38-6 propionaldehyde 
• 74-96-4 ethyl bromide 
• 107-02-8 acrolein 
• 4187-86-4 pent-1-yn-3-ol 

Downstream Products

• 7348-71-2 (E)-1-bromo-2-pentene 
• 504-60-9 penta-1,3-diene 
• 591-95-7 penta-1,2-diene 
• 31844-95-8 2-bromopent-1-ene 
• 20599-27-3 1-bromopent-2-ene 
• 10071-60-0 1-chloro-2-pentene 
• 24356-00-1 3-chloro-1-pentene 
• 1629-58-9 4-penten-3-one 
• 96-22-0 pentan-3-one 
• 1576-96-1 (E)-2-penten-1-ol 
• 18388-22-2 3-(trimethylsilyl)-1-pentene 
• 7472-25-5 1,1-dimethoxy-butan-2-ol 
• 114490-67-4 4-((E)-Pent-2-enyl)-2-phenyl-4-trifluoromethyl-4H-oxazol-5-one 
• 4050-45-7 trans-2-hexene 

Relevant academic research and scientific papers

Copper(i) pyrimidine-2-thiolate cluster-based polymers as bifunctional visible-light-photocatalysts for chemoselective transfer hydrogenation of α,β-unsaturated carbonyls

The photoinduced chemoselective transfer hydrogenation of unsaturated carbonyls to allylic alcohols has been accomplished using cluster-based MOFs as bifunctional visible photocatalysts. Assemblies of hexanuclear clusters [Cu6(dmpymt)6] (1, Hdmpymt = 4,6-dimethylpyrimidine-2-thione) as metalloligands with CuI or (Ph3P)CuI yielded cluster-based metal organic frameworks (MOFs) {[Cu6(dmpymt)6]2[Cu2(μ-I)2]4(CuI)2}n (2), {[Cu6(dmpymt)6]2[Cu2(μ-I)2]4}n (3), respectively. Nanoparticles (NPs) of 2 and 3 served both as photosensitizers and photocatalysts for the highly chemoselective reduction of unsaturated carbonyl compounds to unsaturated alcohols with high catalytic activity under blue LED irradiation. The photocatalytic system could be reused for several cycles without any obvious loss of efficiency.

Nitrogen-fixing of ultrasmall Pd-based bimetallic nanoclusters on carbon supports

Synthesis of supported Pd-based bimetallic catalysts is of great importance in the heterogeneous catalysis field owing to their optimal geometric and electronic effects. Downsizing active metals to ultrasmall nanocluster (2-reduction at 400–500 °C. Through the nitrogen-fixing strategy, we prepare 9 sub-2 nm Pd-based bimetallic nanocluster catalysts by conventional impregnation process. The prepared supported bimetallic Pd-Pb nanocluster catalyst exhibit a high turnover frequency of 1092 h?1 for the semihydrogenation of phenylacetylene under a mild condition (30 °C, 5 bar H2), along with a high selectivity of >93% to styrene, demonstrating the alloying and small-size effects in the bimetallic nanocluster catalysts.

Hydrogenative Cyclopropanation and Hydrogenative Metathesis

The unusual geminal hydrogenation of a propargyl alcohol derivative with [CpXRuCl] as the catalyst entails formation of pianostool ruthenium carbenes in the first place; these reactive intermediates can be intercepted with tethered alkenes to give either cyclopropanes or cyclic olefins as the result of a formal metathesis event. The course of the reaction is critically dependent on the substitution pattern of the alkene trap.

Access to Saturated Thiocyano-Containing Azaheterocycles via Selenide-Catalyzed Regio-A nd Stereoselective Thiocyanoaminocyclization of Alkenes

An efficient route for the synthesis of saturated thiocyano-containing azaheterocycles by selenide-catalyzed regio-A nd stereoselective thiocyanoaminocyclization of alkenes is disclosed. The desired products were obtained in moderate to high yields under mild conditions. The generality of this method was elucidated by its efficient application in thiocyano oxycyclization of alkenes.

Rh-Catalyzed Regioselective Dialkylation of Cage B-H bonds in o-Carboranes: Oxidative Heck Reactions via an Enol Isomerization

In the presence of a carboxylic acid directing group, Rh-catalyzed regioselective directed dialkylation of B(4,5)-H bonds in o-carboranes and oxidative coupling with allylic alcohols is reported. This strategy constructs a series of 4,5-dialkylated o-carboranes in good yields with excellent regioselectivity. A possible catalytic cycle is proposed that involves a tandem sequence of Rh-catalyzed cage B-H activation, alkene insertion, selective β-H elimination, enol isomerization, and decarboxylation.

Switchable Chemoselective Transfer Hydrogenations of Unsaturated Carbonyls Using Copper(I) N-Donor Thiolate Clusters

Unsaturated alcohols and saturated carbonyls are important chemical, pharmaceutical, and biochemical intermediates. We herein report an efficient transfer hydrogenation protocol in which conversion of unsaturated carbonyl compounds to either unsaturated alcohols or saturated carbonyls was catalyzed by Cu(I) N-donor thiolate clusters along with changing hydrogen source (isopropanol or butanol) and base (NaOH or K2CO3). Mechanistic studies supported by DFT transition state modeling indicate that such a chemoselectivity can be explained by the relative concentrations of Cu(I) monohydride and protonated Cu(I) hydride complexes in each catalytic system.

Ruthenium(II)-Catalyzed Regio- and Stereoselective C-H Allylation of Indoles with Allyl Alcohols

A ruthenium-catalyzed C-H allylation of indoles with allyl alcohols via β-hydroxide elimination is reported. Without external oxidants and expensive additives, this reaction features mild reaction conditions, compatibility with various functional groups, and good to excellent regioselectivity and stereoselectivity.

Stereoselective Rh-Catalyzed Hydrogenative Desymmetrization of Achiral Substituted 1,4-Dienes

Highly efficient catalytic stereoselective hydrogenative desymmetrization reactions mediated by rhodium complexes derived from enantiopure phosphine-phosphite (P-OP) ligands are described. The highest performing ligand, which contains a TADDOL-derived phosphite fragment [TADDOL = (2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)], presented excellent catalytic properties for the desymmetrization of a set of achiral 1,4-dienes, providing access to the selective formation of a variety of enantioenriched secondary and tertiary alcohols (six examples, up to 92% ee).

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents

The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.