13991-37-2

Basic information

• Product Name: TRANS-2-PENTENOIC ACID
• Synonyms: (E)-pent-2-en-1-oicacid;2-Pentenoic acid, (E)-;2-Pentenoicacid,(E)-;2-PENTENOIC ACID;FEMA 4193;(E)-2-PENTENOIC ACID;BETA-ETHYL ACRYLIC ACID;TRANS-PENT-2-ENOIC ACID
• CAS NO: 13991-37-2
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 237-791-9
• Mol File: 13991-37-2.mol
• Article Data: 35

Chemical Properties

• Melting Point: 9-11 °C(lit.)
• Boiling Point: 106 °C20 mm Hg(lit.)
• Flash Point: 102 °C
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.99 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 60g/l
• PKA: pK1:4.70 (25°C)
• Explosive Limit: 1.6%(V)
• BRN: 1720312
• CAS DataBase Reference: TRANS-2-PENTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2-PENTENOIC ACID(13991-37-2)
• EPA Substance Registry System: TRANS-2-PENTENOIC ACID(13991-37-2)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• RTECS: SB2750000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 13991-37-2(Hazardous Substances Data)

Usage

Chemical Description

Trans-2-pentenoic acid is an organic compound with the formula C5H8O2.

Description

TRANS-2-PENTENOIC ACID, also known as 2-pentenoic acid, is a naturally occurring organic compound that can be found in various fruits and beverages, such as bananas and beer. It is characterized by its clear colorless to light yellow liquid appearance and a sour caramellic aroma. TRANS-2-PENTENOIC ACID possesses a sour acetic buttery taste with a taste threshold value of 25 ppm in water and a medium strength odor, reminiscent of cheese, which is recommended to be smelled in a 1% solution or less.

Uses

Used in Pharmaceutical Industry:
TRANS-2-PENTENOIC ACID is used as a key component in the preparation of new nonsteroidal human androgen receptor (hAR) agonists. These agonists are derived from an hAR antagonist pharmacophore, 2(1H)-piperidino[3,2-g]quinolinone, and have potential applications in the development of novel therapeutic agents for various medical conditions.
Used in Flavor and Fragrance Industry:
Due to its unique sour caramellic aroma and cheese-like odor, TRANS-2-PENTENOIC ACID can be utilized as a flavoring agent in the food and beverage industry. It can be added to various products to enhance their taste and aroma, providing a distinct and appealing sensory experience for consumers.
Used in Research and Development:
TRANS-2-PENTENOIC ACID can also be employed in research and development for the study of its chemical properties and potential applications in various fields. Its sour acetic buttery taste and medium strength odor make it an interesting compound for further investigation and potential use in the development of new products and technologies.

InChI:InChI=1/C5H8O2/c1-2-3-4-5(6)7/h3-4H,2H2,1H3,(H,6,7)/p-1/b4-3+

Upstream product

• 42482-20-2 3-hydroxyvaleric acid 
• 4436-74-2 hex-3-ene-1,6-dicarboxylic acid 
• 141-82-2 malonic acid 
• 64-19-7 acetic acid 
• 123-38-6 propionaldehyde 
• 106-98-9 1-butylene 
• 1822-71-5 n-pentylsodium 
• 109-66-0 pentane 
• 107-01-7 butene-2 
• 1576-86-9 2-pentenal 
• 5204-64-8 3-pentenoic acid 
• 118375-92-1 3-bromopentanoic acid 
• 7732-18-5 water 
• 590-18-1 (Z)-2-Butene 

Downstream Products

• 15790-87-1 Methyl (E)-2-pentenoate 
• 802294-64-0 propionic acid 
• 80-59-1 Tiglic acid 
• 78-93-3 butanone 
• 2445-93-4 ethyl 2-pentenoate 
• 30368-22-0 (+/-)-methyl 3-phenylpentanoate 
• 16433-43-5 4-phenyl-1-pentanoic acid 
• 2845-27-4 3-phenylpentanoic acid 
• 88239-45-6 C₈H₁₆O₂Si 
• 74502-25-3 (1R,6S)-2-Acetoxy-6-ethyl-cyclohex-3-enecarboxylic acid 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 40920-68-1 3-methyl-5-ethylcyclohex-2-en-1-one 
• 137204-61-6 5-ethyl-3-phenyl-2-cyclohexenone 
• 137204-63-8 3,5-diphenyl-5-methyl-2-cyclohexenone 

Relevant articles and documents

A Convenient Synthetic Route to (E)-2-Penten-1-ol

-

Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols

A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.

Palladium catalyzed carbonylations of alkenyl halides with formic acid to get corresponding Α,Β-unsaturated carboxylic acids and esters

Palladium-catalysed carbonylation reactions have been developed in the presence of formic acid as carbon monoxide source. α,β-Unsaturated carboxylic acids and esters were synthesized by the transformation of alkenyl halides in moderate to good yields. The selection of the base proved to be crucial regarding the reaction outcome. A set of various substrates were proven under optimised reaction conditions. Compared to aliphatic alcohols, phenols showed excellent reactivity as O-nucleophiles.

Lithium perchlorate catalyzed electrophilic activation: A convenient one-pot synthesis of trans-cinnamic acids

Background: Currently perchlorate catalysts gain much attention in organic synthesis due to ease of operation, wide applicability, high yield, and economy. This is evident through increasing number of citation related to their application in industry as well as other allied fields. The aim of this paper is to describe a methodology using lithium perchlorate to catalyze the Knoevenagel condensation reaction for the synthesis of biologically active trans-cinnamic acid in good to excellent yield. Methods: We discuss herein an economic, user-friendly one-pot synthesis of trans-cinnamic acids by refluxing a mixture of a malonic acid with aryl aldehyde in pyridine. The product was easily isolated via filtration and thereafter washed and characterized by spectroscopic methods. Results: This method is robust, stereoselective and high yielding. It can be utilized to synthesize a wide array of trans-cinnamic acids in good to excellent yield using 20% of lithium perchlorate catalyst. It is also useful in the synthesis of aliphatic α,β-unsaturated carboxylic acid. Conclusion: The role of lithium perchlorate as a mild catalyst in the synthesis of trans-cinnamic acid was explored. The reactions afforded a good yield of various products with simpler isolation.