Valeric acid

Base Information

• Chemical Name: Valeric acid
• CAS No.: 109-52-4
• Deprecated CAS: 12124-87-7,2243145-76-6,2486087-46-9
• Molecular Formula: C5H10O2
• Molecular Weight: 102.133
• Hs Code.: 29156090
• European Community (EC) Number: 203-677-2
• ICSC Number: 0346
• NSC Number: 406833
• UN Number: 3265
• UNII: GZK92PJM7B
• DSSTox Substance ID: DTXSID7021655
• Nikkaji Number: J1.504K
• Wikipedia: Valeric acid,Valeric_acid
• Wikidata: Q407796
• Metabolomics Workbench ID: 27
• ChEMBL ID: CHEMBL268736
• Mol file: 109-52-4.mol

Synonyms:lithium pentanoate;n-pentanoic acid;n-pentanoic acid, 11C-labeled;n-pentanoic acid, 11C-labeled sodium salt;n-pentanoic acid, ammonium salt;n-pentanoic acid, maganese (+2) salt;n-pentanoic acid, potassium salt;n-pentanoic acid, sodium salt;n-pentanoic acid, zinc salt;valeric acid

Chemical Property of Valeric acid

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 0.15 mm Hg ( 20 °C)
• Melting Point: -20 - -18 °C(lit.)
• Refractive Index: 1.405-1.414
• Boiling Point: 185.3 °C at 760 mmHg
• PKA: 4.84(at 25℃)
• Flash Point: 80.5 °C
• PSA: 37.30000
• Density: 0.966 g/cm³
• LogP: 1.26120
• Storage Temp.: Store below +30°C.
• Solubility.: 40g/l
• Water Solubility.: 40 g/L (20 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 102.068079557
• Heavy Atom Count: 7
• Complexity: 59.1
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Valeric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-52/53
• Safety Statements: 26-36-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CCCCC(=O)O
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion.
• Description: Valeric acid (also pentanoic acid) is a straight chain alkyl carboxylic acid. Valeric acid is mainly used for the synthesis of its esters used in foods, perfume, and cosmetics. Valeric acid is used as an intermediate for applications including ester type lubricants (in aviation turbine oils, fire-resistance hydraulic fluids, and refrigerator oils), plasticizers (dipropyl heptyl phthalate), vinyl stabilizers, and specialty chemicals. It is also used as an odorant in pesticide formulations for use on crops. Valeric acid, or pentanoic acid, is a straight - chain alkyl carboxylic acid with the chemical formula C5H10O2. Like other lowmolecular- weight carboxylic acids, it has a very unpleasant odor. It is found naturally in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Its primary use is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors. Valeric acid appears similar in structure to GHB and the neurotransmitter GABA in that it is a short-chain carboxylic acid, although it lacks the alcohol and amine functional groups that contribute to the biological activities of GHB and GABA, respectively. It differs from valproic acid simply by lacking a 3- carbon side - chain.
• Uses: Valeric acid, is used as a sex attractant of the sugar beet wireworm, Limonius californicus. It is used predominantly as an intermediate in the manufacture of flavors and perfumes, ester type lubricants, plasticizers and vinyl stabilizesrs. It is a food additive used as a synthetic flavoring substance dan adjuvant. It is an inert ingredient in controlling pest. valeric acid is obtained from valerian extract, which is considered skin conditioning. Sex attractant of the sugar beet wireworm, Limonius californicus.1

Technology Process of Valeric acid

There total 493 articles about Valeric 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: 50.6%

cyclohexanol (108-93-0) → hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) + Adipic acid (124-04-9) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + acetic acid (64-19-7,77671-22-8) + hexanoic acid (142-62-1) + valeric acid (109-52-4)

Guidance literature:

With oxygen; ozone; at 40 ℃; for 3h; Product distribution; Rate constant; Mechanism; oth. temperature, oth. time, presence of CCl₄;

Reference yield: 26.3%

butyl-[1,2,4]trioxolane (767-09-9) + butyraldehyde (123-72-8) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + formic acid (64-18-6) + pentanal (110-62-3) + butyric acid (107-92-6) + valeric acid (109-52-4)

Guidance literature:

at 90 ℃; for 6h; Product distribution;

Reference yield: 21.0%

butyl-[1,2,4]trioxolane (767-09-9) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + formic acid (64-18-6) + pentanal (110-62-3) + butyric acid (107-92-6) + valeric acid (109-52-4)

Guidance literature:

In acetic acid; at 90 ℃; for 6h; Product distribution; Thermodynamic data; Rate constant; other solvents, other temperature, ΔS (excit.), ΔG (excit.), ΔH (excit.);

upstream raw materials:

protoanemonin

3,4,5,6-tetrahydro-2H-pyran-2-one

3-methyl-4,5-dihydro-6-oxopyridazine

sodium ethanolate

Downstream raw materials:

n-valeryl chloride

N-ethyl-pentanamide

heptan-3-one

hexyl-methyl-ketone

Refernces

• 1、 Schonecker,Walther,Fischer,Nestler,Braunlich,Eibisch,Droescher. "A nickelacycle as propionic acid equivalent for carbon-carbon coupling reactions; application to the synthesis of C25 steroid carboxylic acids". . p. 1257 - 1260. Retrieved 1990.
• 2、 Kabalka, George W.,Li, Nan-Sheng,Tejedor, David,Malladi, Rama R.,Trotman, Sarah. "Synthesis of (E)-1-Aryl-1-alkenes via a Novel BF3·OEt2-Catalyzed Aldol-Grob Reaction Sequence". . p. 3157 - 3161. Retrieved 1999.
• 3、 Sonoda,Tsutsumi. "-". . p. 505,509. Retrieved 1959.
• 4、 Ganieva,Ganiev,Grabovskiy,Kabalnova. "Oxidation of valeraldehyde by chlorine dioxide". . p. 2332 - 2334. Retrieved 2008.
• 5、 Choudary,Valli,Prasad. "A novel montmorillonite - KMnO4 system for the oxidation of alkenes under triphase conditions". . p. 2007 - 2013. Retrieved 1991.
• 6、 Zhang, Guangcheng,Li, Wei,Fan, Guoli,Yang, Lan,Li, Feng. "Controlling product selectivity by surface defects over MoOx-decorated Ni-based nanocatalysts for γ-valerolactone hydrogenolysis". . p. 100 - 111. Retrieved 2019.
• 7、 Baumeister, Tobias,Kitzler, Hannes,Obermaier, Klemens,Zikeli, Stefan,R?der, Thorsten. "Two-Phase Flow Oxidation of Valeraldehyde with O2 in a Microstructured Reactor". . p. 1576 - 1579. Retrieved 2015.
• 8、 Carraro, Mauro,Sandei, Luca,Sartorel, Andrea,Scorrano, Gianfranco,Bonchio, Marcella. "Hybrid polyoxotungstates as second-generation POM-based catalysts for microwave-assisted H2O2 activation". . p. 3671 - 3674. Retrieved 2006.
• 9、 Troyanskii, E. I.,Svitan'ko, I. V.,Ioffe, V. A.,Nikishin, G. I.. "OXIDATIVE SUBSTITUTION OF THE AMINO GROUP IN PRIMARY ALIPHATIC ANINES". . p. 1932. Retrieved 1982.
• 10、 Kabalka, George W.,Tejedor, David,Li, Nan-Sheng,Reddy, Malladi,Trotman, Sarah. "Boron trifluoride induced fragmentation of β-Aryl-β-hydroxyketones". . p. 8071 - 8072. Retrieved 1998.