4-Hydroxypentanoic acid

Base Information

• Chemical Name: 4-Hydroxypentanoic acid
• CAS No.: 13532-37-1
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.133
• European Community (EC) Number: 236-884-1
• UNII: 58B139Q3RL
• DSSTox Substance ID: DTXSID60928958
• Nikkaji Number: J52.191D
• Wikipedia: Gamma-Hydroxyvaleric_acid
• Wikidata: Q5520261
• Metabolomics Workbench ID: 1286
• ChEMBL ID: CHEMBL169219
• Mol file: 13532-37-1.mol

Synonyms:4-hydroxyvalerate;4-hydroxyvaleric acid;4-Me-GHB;gamma-methyl-gamma-hydroxybutyric acid

Chemical Property of 4-Hydroxypentanoic acid

Chemical Property:

• Vapor Pressure: 0.000564mmHg at 25°C
• Boiling Point: 277.3°Cat760mmHg
• PKA: pK1:4.686 (18°C)
• Flash Point: 135.7°C
• PSA: 57.53000
• Density: 1.14g/cm³
• LogP: 0.23200
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 118.062994177
• Heavy Atom Count: 8
• Complexity: 79.7

Purity/Quality:

99%, ^*data from raw suppliers

4-HYDROXYPENTANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)O

Technology Process of 4-Hydroxypentanoic acid

There total 45 articles about 4-Hydroxypentanoic 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: 93.0%

levulinic acid (123-76-2) → 4-hydroxyvaleric acid (13532-37-1,103712-26-1) + 5-methyl-dihydro-furan-2-one (108-29-2)

Guidance literature:

With 5% active carbon-supported ruthenium; hydrogen; In water; at 110 ℃; for 0.75h; under 15451.5 Torr; Autoclave;

Reference yield: 74.0%

5-methyl-dihydro-furan-2-one (108-29-2) → 4-hydroxyvaleric acid (13532-37-1,103712-26-1)

Guidance literature:

With water; sodium hydroxide; In 1,4-dioxane; for 1h;

Reference yield: 73.0%

4-oxopentanoic acid ethyl ester (539-88-8) → 4-hydroxyvaleric acid (13532-37-1,103712-26-1) + 5-methyl-dihydro-furan-2-one (108-29-2)

Guidance literature:

With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); hydrogen; sodium methylate; In ethanol; at 60 ℃; for 3h; under 15001.5 Torr; Solvent; Pressure; Reagent/catalyst; Catalytic behavior; Autoclave; Sealed tube;

DOI:10.1039/c9gc01651a

upstream raw materials:

1,4-Pentanediol

(S)-5-hexen-2-ol

chloroform

levulinic acid

Downstream raw materials:

5-methyl-dihydro-furan-2-one

(R)-5-methyl-2-oxotetrahydrofuran

(S)-γ-valerolactone

(S)-4-HVA sodium salt

Refernces

• 1、 Fishler, Yuval,Holewinski, Adam,Lucas, Francisco W. S.. "Tuning the selectivity of electrochemical levulinic acid reduction to 4-hydroxyvaleric acid: A monomer for biocompatible and biodegradable plastics". supporting information. p. 9154 - 9164. Retrieved 2021/11/27.
• 2、 Li, Jie,Zhao, Shuaiheng,Li, Zhen,Liu, Dan,Chi, Yingnan,Hu, Changwen. "Efficient Conversion of Biomass-Derived Levulinic Acid to γ-Valerolactone over Polyoxometalate@Zr-Based Metal-Organic Frameworks: The Synergistic Effect of Bro?nsted and Lewis Acidic Sites". supporting information. p. 7785 - 7793. Retrieved 2021/05/04.