16957-70-3

Basic information

• Product Name: trans-2-Methyl-2-pentenoic acid
• Synonyms: FEMA NUMBER 3195;FEMA 3195;(e)-2-methylpent-2-en-1-oic acid;RARECHEM AL BE 0127;STRAWBERRIFF;(2E)-2-Methyl-2-pentenoic acid;(e)-2-pentenoicaci;TRANS-2-METHYL-2-PENTENOIC ACID 98+% F
• CAS NO: 16957-70-3
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• EINECS: 241-026-4
• Product Categories: C6;Carbonyl Compounds;Carboxylic Acids
• Mol File: 16957-70-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 26-28 °C(lit.)
• Boiling Point: 123-125 °C30 mm Hg(lit.)
• Flash Point: 226 °F
• Appearance: clear colorless to pale yellow liquid
• Density: 0.979 g/mL at 25 °C
• Vapor Density: >1 (vs air)
• Vapor Pressure: 0.0554mmHg at 25°C
• Refractive Index: n20/D 1.46(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.00±0.19(Predicted)
• Water Solubility: insoluble
• CAS DataBase Reference: trans-2-Methyl-2-pentenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2-Methyl-2-pentenoic acid(16957-70-3)
• EPA Substance Registry System: trans-2-Methyl-2-pentenoic acid(16957-70-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 2
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 16957-70-3(Hazardous Substances Data)

Usage

Description

Trans-2-Methyl-2-pentenoic acid is a clear colorless to pale yellow liquid with a fruity odor. It has been investigated for its adsorption and desorption properties in dichloromethane using in situ attenuated total reflection infrared spectroscopy. The asymmetric hydrogenation of this compound has also been studied over two well-defined Engelhard Pd/Al2O3 catalysts modified with cinchonidine. It is known to have a sour, acidic, sweaty, berry, and fruit-like taste at a concentration of 50 ppm and has been reported to be found in strawberries.

Uses

Used in Flavor Industry:
Trans-2-Methyl-2-pentenoic acid is used as a flavoring agent for its distinctive sour, acidic, sweaty, berry, and fruit-like taste. Its unique taste profile makes it a valuable addition to the flavor industry, where it can be used to enhance the taste of various food and beverage products.
Used in Chemical Research:
Due to its chemical properties and behavior in reactions, trans-2-Methyl-2-pentenoic acid is used as a research compound in the field of chemistry. It serves as a subject for studying adsorption and desorption processes, as well as asymmetric hydrogenation reactions, which can contribute to the development of new chemical processes and applications.
Used in Fragrance Industry:
The fruity odor of trans-2-Methyl-2-pentenoic acid makes it a suitable candidate for use in the fragrance industry. It can be used to create or enhance the scent of various perfumes, colognes, and other scented products, providing a unique and appealing aroma to consumers.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, compounds with similar properties to trans-2-Methyl-2-pentenoic acid have been known to be used in the pharmaceutical industry for various applications, such as drug synthesis or as active ingredients in medications. Further research and development could potentially lead to new uses for this compound in the pharmaceutical sector.

Preparation

By distillation of 2-hydroxy-2-methylvaleric acid (cis-form).

Flammability and Explosibility

Notclassified

InChI:InChI=1/C6H10O2/c1-3-4-5(2)6(7)8/h4H,3H2,1-2H3,(H,7,8)/p-1/b5-4+

Upstream product

• 97-61-0 2-Methylpentanoic acid 
• 14250-96-5 2-methyl-2-pentenal 
• 623-36-9 (E)-2-methylpent-2-enal 
• 1617-40-9 ethyl (E)-2-methyl-2-pentenoate 
• 84307-86-8 1,1-Bis(methylthio)-2-methyl-1-penten-3-ol 
• 79140-68-4 (E)-2-Methyl-1-trimethylsilanyl-pent-2-en-1-one 
• 123-38-6 propionaldehyde 
• 598-72-1 2-Bromopropionic acid 
• 1567-14-2 methyl (2E)-2-methyl-2-pentenoate 
• 80-59-1 Tiglic acid 
• 74-88-4 methyl iodide 
• 3142-72-1 2-methyl-2-pentenoic acid 
• 4111-09-5 2-Hydroxy-2-methyl-pentanenitrile 
• 146984-85-2 ethyl (E)-2-iodo-2-pentenoate 

Downstream Products

• 1187-82-2 (S)-2-methylpentanoic acid 
• 49642-47-9 methyl (R)-2-methylbutyric acid 
• 80510-15-2 (+)-(1S)-1-methylbutyl (2E)-2-methylpent-2-enoate 
• 140461-21-8 (E)-(R)-⁽¹⁾-1-methylbutyl 2-methyl-2-pentenoate 
• 58683-58-2 methyl (E)-4-bromo-2-methyl-2-pentenoate 
• 698387-93-8 (2E,4E)-ethyl 6-(4-dimethylaminophenylsulfanyl)-4-methyl-2,4-heptadienoate 
• 875737-07-8 methyl (E)-4-(4-dimethylaminophenylsulfanyl)-2-methyl-2-pentenoate 
• 875737-08-9 (E)-4-(4-dimethylaminophenylsulfanyl)-2-methyl-2-penten-1-ol 
• 1567-14-2 methyl (2E)-2-methyl-2-pentenoate 
• 412284-09-4 3-ethyl-1,2-dimethyl-5-methoxyindole 
• 39255-32-8 manzanate 
• 105-30-6 (S)-2-methyl-1-pentanol 

Relevant articles and documents

Stereospecificity of the dehydratase domain of the erythromycin polyketide synthase

The dehydratase (DH) domain of module 4 of the 6-deoxyerythronolide B synthase (DEBS) has been shown to catalyze an exclusive syn elimination/syn addition of water. Incubation of recombinant DH4 with chemoenzymatically prepared anti-(2R,3R)-2-methyl-3-hydroxypentanoyl-ACP (2a-ACP) gave the dehydration product 3-ACP. Similarly, incubation of DH4 with synthetic 3-ACP resulted in the reverse enzyme-catalyzed hydration reaction, giving an ～3:1 equilbrium mixture of 2a-ACP and 3-ACP. Incubation of a mixture of propionyl-SNAC (4), methylmalonyl-CoA, and NADPH with the DEBS β-ketoacyl synthase-acyl transferase [KS6][AT6] didomain, DEBS ACP6, and the ketoreductase domain from tylactone synthase module 1 (TYLS KR1) generated in situ anti-2a-ACP that underwent DH4-catalyzed syn dehydration to give 3-ACP. DH4 did not dehydrate syn-(2S,3R)-2b-ACP, syn-(2R,3S)-2c-ACP, or anti-(2S,3S)-2d-ACP generated in situ by DEBS KR1, DEBS KR6, or the rifamycin synthase KR7 (RIFS KR7), respectively. Similarly, incubation of a mixture of (2S,3R)-2-methyl-3- hydroxypentanoyl-N-acetylcysteamine thioester (2b-SNAC), methylmalonyl-CoA, and NADPH with DEBS [KS6][AT6], DEBS ACP6, and TYLS KR1 gave anti-(2R,3R)-6-ACP that underwent syn dehydration catalyzed by DEBS DH4 to give (4R,5R)-(E)-2,4- dimethyl-5-hydroxy-hept-2-enoyl-ACP (7-ACP). The structure and stereochemistry of 7 were established by GC-MS and LC-MS comparison of the derived methyl ester 7-Me to a synthetic sample of 7-Me.

Synthesis method of trans-2-methyl-2-pentenoic acid

The invention adopts a Reppe synthesis method to prepare 2-methyl-2-pentenoic acid. The method comprises the following steps: firstly, by taking m-pentadiene, carbon monoxide and water as raw materials, and taking precious metal rhodium salt and an organic phosphine ligand as catalysts, preparing a cis-trans isomeric intermediate of 2-methyl-3-pentenoic acid, and then carrying out isomerization reaction on the obtained intermediate product to generate trans-2-methyl-2-pentenoic acid, namely trans strawberry acid.

Environmentally benign oxidation reaction of aldehydes to their corresponding carboxylic acids using Pd/C with NaBH4 and KOH

Pd/C catalyst in aqueous methanol with sodium borohydride and potassium hydroxide under the air efficiently oxidized aldehydes to their corresponding carboxylic acids at room temperature. The utilization of room temperature reaction, aqueous methanol solvent, and the open-air conditions make this manipulation very interesting for economic and environmental perspectives.