21835-01-8

Basic information

• Product Name: 3-Ethyl-2-hydroxy-2-cyclopenten-1-one
• Synonyms: 2-Cyclopenten-1-one, 3-ethyl-2-hydroxy-;2-Cyclopenten-1-one,3-ethyl-2-hydroxy-(7CI,8CI,9CI);3-ethyl-2-hydroxy-2-cyclopenten-1-on;FEMA 3152;ETHYL CYCLOPENTENOLONE;3-ETHYL-HYDROXY-2-CYCLOPENTEN-1-ONE;3-ETHYL-2-HYDROXY-2-CYCLOPENTEN-1-ONE;3-ETHYL-2-CYCLPENTEN-2-OL-1-ONE
• CAS NO: 21835-01-8
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• EINECS: 244-606-5
• Product Categories: pharmacetical;C7 to C8;Carbonyl Compounds;Ketones;Alphabetical Listings;E-F;Flavors and Fragrances
• Mol File: 21835-01-8.mol

Chemical Properties

• Melting Point: 39.0 to 43.0 °C
• Boiling Point: 75°C/0.3mmHg(lit.)
• Flash Point: 225 °F
• Appearance: White Crystalline powder
• Density: 1.067 g/mL at 25 °C
• Vapor Pressure: 0.00204mmHg at 25°C
• Refractive Index: n20/D 1.476
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol,Ether
• PKA: 9.17±0.20(Predicted)
• CAS DataBase Reference: 3-Ethyl-2-hydroxy-2-cyclopenten-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethyl-2-hydroxy-2-cyclopenten-1-one(21835-01-8)
• EPA Substance Registry System: 3-Ethyl-2-hydroxy-2-cyclopenten-1-one(21835-01-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/22-43
• Safety Statements: 26-36-36/37
• WGK Germany: 3
• Hazardous Substances Data: 21835-01-8(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
3-Ethyl-2-hydroxy-2-cyclopenten-1-one is used as a flavoring agent for its ability to impart caramel, coconut, and other sweet, brown, and fruity notes to various products.
Used in Food Industry:
In the food industry, 3-Ethyl-2-hydroxy-2-cyclopenten-1-one is used as an additive to enhance the flavor of products, providing a caramellic, maple, brown sugar, rum, and whiskey taste. Its flavor-enhancing properties make it a valuable component in the creation of a wide range of food items.

Preparation

From 5-methyl-3,5-dicarbethoxy-2-cyclopen-ten-2-ol-one and phosphoric acid; by a patented process; also from dimethyl adipate.

InChI:InChI=1/C7H10O2/c1-2-5-3-4-6(8)7(5)9/h9H,2-4H2,1H3

Upstream product

• 50786-06-6 2-methyl-1-oxa-spiro[2.4]heptan-4-one 
• 27332-51-0 2‐hydroxy‐2‐vinylcyclopentan‐1‐one 
• 76742-14-8 1-acetoxy-2,5-heptandion 
• 21891-35-0 2,3-epoxy-2-ethyl-cyclopentanone 
• 10088-87-6 4,5-dioxo-cyclopentane-1,3-dicarboxylic acid diethyl ester 
• 75-03-6 ethyl iodide 
• 14189-85-6 2-methoxy-3-methylcyclopent-2-en-1-one 
• 74-88-4 methyl iodide 
• 6838-66-0 1,2-bis((trimethylsilyl)oxy)cyclopent-1-ene 
• 62952-60-7 C₉H₈O₆^(2-)*2Na⁽¹⁺⁾ 
• 3008-40-0 cyclopentane-1,2-dione 
• 80-71-7 2-hydroxy-3-methylcyclopent-2-en-1-one 
• 41535-58-4 3-ethyl-2-methoxy-2-cyclopenten-1-one 
• 50-00-0 formaldehyd 

Downstream Products

• 303183-89-3 2-ethyl-5-oxotetrahydrofuran-2-carboxylic acid 
• 303183-89-3 (S)-2-ethyl-5-oxotetrahydrofuran-2-carboxylic acid 
• 594845-75-7 C₇H₁₀O₄ 
• 1117-74-4 4-oxohexanoic acid 

Relevant articles and documents

High yield "one-pot" synthesis of 2-hydroxy-3-methylcyclopent-2-en-1-one and related compounds

A convenient "one-pot" modification of a conventional synthetic route affords 2-hydroxy-3-methylcyclopent-2-en-1-one and related compounds in high overall yields.

The effect of pH on the formation of aroma compounds produced by heating a model system containing l-ascorbic acid with l-threonine/l-serine

The identification of aroma compounds, formed from the reactions of l-ascorbic acid with l-threonine/l-serine at five different pH values (5.00, 6.00, 7.00, 8.00, or 9.55) and 143 ± 2 °C for 2 h, was performed using a SPME-GC-MS technique, and further use

Reactions of 1,2-bis(trimethylsilyloxy)cycloalkenes with the diethyl acetals of aldehydes

Lewis acid-mediated reactions of 1,2-bis(trimethylsilyloxy)-cyclobutene with acetals derived from a variety of aldehydes, followed by treatment with Amberlyst 15 resin in TFA, yielded 1,3-cyclopentanedione products, but reactions with 3,3-dimethyl-1,2-bis(trimethylsilyloxy)cyclobutene led to 1,2-cyclopentanediones. Reactions of 1,2-bis(trimethylsilyloxy)-cyclopentene gave intermediates that did not undergo skeletal rearrangement with Amberlyst 15 resin in TFA.

Acetoacetic acid ester derivatives for the manufacture of α-hydroxycarbonyl compounds

The invention is concerned with a novel process for the manufacture of compounds of the formula STR1 wherein R1 signifies C1-5 -alkyl, especially methyl, ethyl, propyl or isopropyl, and the radicals R2 each independently represent hydrogen or C1-5 -alkyl, especially hydrogen or methyl, ethyl, propyl or isopropyl. The process is characterized in that a compound of the formula STR2 wherein R stands for C1-4 -alkoxy, chlorine, bromine or C1-4 -alkanoyloxy, R1 and R2 have the above significance and R3 represents C1-4 -alkyl. is hydrolyzed and subjected to an aldol condensation and, where R=C1-4 -alkoxy, the reaction product is subsequently subjected to an acid treatment. The compounds I are for the most part known flavoring substances.

ADDITION VON ALDEHYDEN AN AKTIVIERTE DOPPELBINDUNGEN, XXVII. MITTEILUNG : EIN EINFACHER WEG ZU 2-HYROXY-CYCLOPENTENONEN

A new, easy synthetic route to 2-hydroxy-3-alkyl-cyclopentenones starting from the thiazolium salt catalyzed addition of aldehydes to 1-acetoxy-3-buten-2-one is described.

Method of preparing 2-hydroxy-3-alkyl-2-cyclopenten-1-one

A method of preparing 2-hydroxy-3-alkyl-2-cyclopenten-1-one which comprises reacting 2-alkyl-5-carboalkoxycyclopentanone with nitrite in the presence of water and alkali; rendering the reaction system acidic; and either treating the mass for hydrolysis by heating or carrying out oxime exchange reaction in the presence of an aliphatic lower carbonyl compound added as an acceptor to the acidified reaction system.