2-Propyl-4-pentenoic acid

Base Information

• Chemical Name: 2-Propyl-4-pentenoic acid
• CAS No.: 1575-72-0
• Deprecated CAS: 124815-86-7
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.198
• Hs Code.: 2916190090
• European Community (EC) Number: 803-182-7
• UNII: 2GYI36I25W
• DSSTox Substance ID: DTXSID20881257
• Nikkaji Number: J362.530C
• Wikidata: Q27149680
• Metabolomics Workbench ID: 42519
• ChEMBL ID: CHEMBL1367
• Mol file: 1575-72-0.mol

Synonyms:2-propyl-4-pentenoic acid;2-propyl-4-pentenoic acid, (+-)-isomer;2-propyl-4-pentenoic acid, (R)-isomer;2-propyl-4-pentenoic acid, (S)-isomer;4-en-VPA;4-ene valproic acid;4-ene VPA;delta(4)-VPA

Chemical Property of 2-Propyl-4-pentenoic acid

Chemical Property:

• Vapor Pressure: 0.0257mmHg at 25°C
• Boiling Point: 228.8°Cat760mmHg
• PKA: 4.70±0.20(Predicted)
• Flash Point: 126.2°C
• PSA: 37.30000
• Density: 0.943g/cm³
• LogP: 2.06340
• Storage Temp.: Refrigerator
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 118

Purity/Quality:

NLT 98% ^*data from raw suppliers

(+/-)-2-Propyl-4-pentenoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic.
• Hazard Codes: Moderately toxic.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(CC=C)C(=O)O
• Description: (±)-2-propyl-4-Pentenoic acid (4-ene VPA) is a major metabolite of valproic acid . It undergoes β-oxidation to form reactive metabolites that induce hepatotoxicity in rats. 4-ene VPA is also neuroteratogenic, reducing forebrain size and inducing deformation of the neural tube in mouse embryos.
• Uses: A metabolite of Valproic Acid

Technology Process of 2-Propyl-4-pentenoic acid

There total 12 articles about 2-Propyl-4-pentenoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 36.0%

allyl bromide (106-95-6) + valeric acid (109-52-4) → 2-n-propyl-4-pentenoic acid (1575-72-0)

Guidance literature:

valeric acid; With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃;

allyl bromide; In tetrahydrofuran; at 0 - 20 ℃;

With hydrogenchloride; water; In tetrahydrofuran;

DOI:10.1021/ol8029005

Reference yield:

2-propyl-2-ethoxycarbonylpenten-4-oic acid ethyl ester (59726-38-4) → 2-n-propyl-4-pentenoic acid (1575-72-0)

Guidance literature:

Multistep reaction; (i) aq. KOH, (ii) (heating);

DOI:10.1248/cpb.24.538

Reference yield:

diethyl propylmalonate (2163-48-6) → 2-n-propyl-4-pentenoic acid (1575-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium ethanolate / ethanol / 78 °C

2: KOH / H₂O; ethanol / Heating

3: 120 - 180 °C / Heating

With potassium hydroxide; sodium ethanolate; In ethanol; water; 1: Alkylation / 2: Hydrolysis / 3: Decarboxylation;

DOI:10.1021/tx950216s

upstream raw materials:

allyl-propyl-malonic acid

2-propyl-2-ethoxycarbonylpenten-4-oic acid ethyl ester

(2-propenyl)propanedioic acid diethyl ester

propyl bromide

Downstream raw materials:

4,5-Dihydroxy-2-propylpentanoic acid-γ-lactone

Refernces

• 1、 Peng, Bo,Geerdink, Danny,Maulide, Nuno. "Electrophilic rearrangements of chiral amides: A traceless asymmetric α-allylation". supporting information. p. 14968 - 14971. Retrieved 2013/11/06.
• 2、 Werstuck, Geoff H.,Kim, Anna J.,Brenstrum, Timothy,Ohnmacht, Stephan A.,Panna, Ella,Capretta, Alfredo. "Examining the correlations between GSK-3 inhibitory properties and anti-convulsant efficacy of valproate and valproate-related compounds". . p. 5465 - 5467. Retrieved 2007/10/03.