13392-69-3

Basic information

• Product Name: 5-hydroxyvaleric acid
• Synonyms: 5-hydroxyvaleric acid;5-Hydroxy Pentanoic Acid;Pentanoic acid, 5-hydroxy-;5-hydroxyvaleric acid, solidum salt
• CAS NO: 13392-69-3
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.13
• Mol File: 13392-69-3.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 268.2°Cat760mmHg
• Flash Point: 130.3°C
• Appearance: /
• Density: 1.144g/cm³
• Vapor Pressure: 0.00105mmHg at 25°C
• Refractive Index: 1.46
• PKA: 4.71±0.10(Predicted)
• CAS DataBase Reference: 5-hydroxyvaleric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxyvaleric acid(13392-69-3)
• EPA Substance Registry System: 5-hydroxyvaleric acid(13392-69-3)

Safety Data

• Hazardous Substances Data: 13392-69-3(Hazardous Substances Data)

Usage

Definition

ChEBI: An omega-hydroxy fatty acid consisting of pentanoic acid carrying a hydroxy group at C-5.

Synthesis Reference(s)

Synthetic Communications, 11, p. 583, 1981 DOI: 10.1080/00397918108063628

InChI:InChI=1/C5H10O3/c6-4-2-1-3-5(7)8/h6H,1-4H2,(H,7,8)

Upstream product

• 694-54-2 tetrahydro-2H-2-pyranol 
• 111-29-5 1 ,5-pentanediol 
• 6280-87-1 δ-chlorovaleronitrile 
• 4221-03-8 5-hydroxypentanal 
• 6778-33-2 5-(trimethylammonio)pentanoate 
• 120-92-3 cyclopentanone 
• 108-55-4 glutaric anhydride, 
• 60-29-7 diethyl ether 
• 7647-01-0 hydrogenchloride 
• 88-14-2 2-furanoic acid 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 7722-84-1 dihydrogen peroxide 
• 7732-18-5 water 

Downstream Products

• 110-94-1 1,5-pentanedioic acid 
• 2067-33-6 5-bromopentanoic acid 
• 2034-25-5 5-hydroxypentanoic acid hydrazide 
• 14660-52-7 ethyl 5-bromovalerate 
• 1620516-94-0 5-hydroxy-N-(3-(5-p-tolyl-1,3,4-oxadiazol-2-yl)phenyl)pentanamide 
• 134848-96-7 benzyl 5-hydroxy pentanoate 
• 89855-60-7 5-(dimethylamino)pentanoic acid 
• 1346933-11-6 benzyl 5-(dimethylamino)pentanoate 
• 627-93-0 hexanedioic acid dimethyl ester 
• 4547-43-7 methyl 6-hydroxycaproate 
• 1119-40-0 Dimethyl glutarate 
• 14273-92-8 methyl 5-hydroxypentanoate 
• 931-17-9 1,2-Cyclohexanediol 
• 106-65-0 Dimethyl succinate 

Relevant articles and documents

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Pentafluoroperbenzoic acid as the efficient reagent for Baeyer–Villiger oxidation of cyclic ketones

The Baeyer–Villiger oxidation of cyclic ketones with pentafluoroperbenzoic acid provides the corresponding lactones in 40–98% yields.

Production of Hydroxy Acids: Selective Double Oxidation of Diols by Flavoprotein Alcohol Oxidase

Flavoprotein oxidases can catalyze oxidations of alcohols and amines by merely using molecular oxygen as the oxidant, making this class of enzymes appealing for biocatalysis. The FAD-containing (FAD=flavin adenine dinucleotide) alcohol oxidase from P. chrysosporium facilitated double and triple oxidations for a range of aliphatic diols. Interestingly, depending on the diol substrate, these reactions result in formation of either lactones or hydroxy acids. For example, diethylene glycol could be selectively and fully converted into 2-(2-hydroxyethoxy)acetic acid. Such a facile cofactor-independent biocatalytic route towards hydroxy acids opens up new avenues for the preparation of polyester building blocks.

Hydrogenolysis of tetrahydrofuran-2-carboxylic acid over tungsten-modified rhodium catalyst

Catalysts for reduction of tetrahydrofuran-2-carboxylic acid (THFCA), which can be synthesized from furfural via oxidation and hydrogenation, were explored among the combinations of noble metal and reducible metal oxide supported on SiO2. Rh-WOx/SiO2 catalysts showed activity in C-O hydrogenolysis at 2-position of THFCA (to δ-valerolactone and 5-hydroxyvaleric acid) and higher yield ratio of these C-O hydrogenolysis products to carboxylic acid hydrogenation products than other bimetallic catalysts. The activity of Rh-WOx/SiO2 catalysts was highest at W/Rh = 0.25 mol/mol. XRD, TPR, CO adsorption and XAFS characterizations showed that the Rh-WOx/SiO2 (W/Rh = 0.25) catalyst contained Rh metal particles with surface modification with isolated W2+ oxide species. The mechanism that hydride-like species formed on Rh atom attacks the C atom at the α-position (2-position) of adsorbed carboxylate on W atom is proposed based on the similar kinetics and similar catalyst structure to Rh-MOx/SiO2 (M = Re, Mo) which is known to be active in THFA hydrogenolysis to 1,5-pentanediol.