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

Chemical Properties

Different sources of media describe the Chemical Properties of 16957-70-3 differently. You can refer to the following data:
1. clear colorless to pale yellow liquid
2. 2-Methyl-2-pentenoic acid has a fruity odor.

Occurrence

Reported found in strawberry

Preparation

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

Taste threshold values

Taste characteristics at 50 ppm: sour, acidic, sweaty, berry and fruit-like.

General Description

Adsorption and desorption of trans-2-methyl-2-pentenoic acid in dichloromethane has been investigated by using in situ attenuated total reflection infrared spectroscopy. Asymmetric hydrogenation of trans-2-methyl-2-pentenoic acid in hexane over two well defined E-40692 and E-5220 Engelhard Pd/Al2O3 catalysts modified with cinchonidine has been studied.

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

• 623-36-9 (E)-2-methylpent-2-enal 
• 133181-02-9 3-hydroxy-2-methylene-pentanoic acid methyl ester 
• 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 
• 55314-57-3 ethyl pent-2-ynoate 
• 1838-77-3 4-methyl-5-hexen-3-ol 
• 1567-14-2 methyl (2E)-2-methyl-2-pentenoate 
• 159999-59-4 2-(acetoxyethylmethyl)acrylic acid methyl ester 
• 637337-87-2 (E)-N-(2-hydroxyethyl)-2-methyl-2-pentenamide 
• 28892-68-4 2-hydroxy-2-methyl-pentanoic acid 
• 80-59-1 Tiglic acid 
• 74-88-4 methyl iodide 
• 123-38-6 propionaldehyde 

Downstream Products

• 16958-19-3 (2E)-2-methyl-2-penten-1-ol 
• 83841-91-2 (E)-2-methyl-2-pentenoyl chloride 
• 137283-13-7 (E)-2-Amino-2-methyl-pent-3-enoic acid 
• 1567-14-2 methyl (2E)-2-methyl-2-pentenoate 
• 54653-29-1 (Z)-2-bromo-2-pentene 
• 54653-30-4 (E)-2-bromo-2-pentene 
• 1617-37-4 cis-2-methyl-pent-2-enoic acid 
• 613672-55-2 trans-2-benzyl-3-ethyl-4-methylisoxazolidin-5-one 
• 613672-55-2 trans-2-benzyl-3-ethyl-4-methylisoxazolidin-5-one 

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.

The thioesterase domain from the pimaricin and erythromycin biosynthetic pathways can catalyze hydrolysis of simple thioester substrates

The recombinant polyketide synthase thioesterase domains from the pimaricin and 6-deoxyerythronolide B biosynthetic pathways catalyze hydrolysis of a number of simple N-acetylcysteamine thioester derivatives. This study demonstrates that thioesterases are not highly substrate selective in formation of the acyl-enzyme intermediate, in contrast to non-ribosomal peptide synthase thioesterase domains that show very high specificity for substrate loading. This observation has important implications for the engineering of biosynthetic pathways to produce polyketide products.