503-74-2 Usage
Description
Isovaleric acid has a characteristic disagreeable odor. It is extremely
penetrating and persistent with a sour taste. May be synthesized by
oxidation of isoamyl alcohol or isovaleric aldehyde.
Chemical Properties
Different sources of media describe the Chemical Properties of 503-74-2 differently. You can refer to the following data:
1. Isovaleric acid has a characteristic disagreeable, rancid, cheese-like odor. It is extremely penetrating and persistent with
a sour taste. May consist of one or a mixture of isomers or n-pentanoic acid and/or 2- or 3-methyl butanoic acid.
Consumption: Annual: 1850.00 lb
2. clear colorless to slightly yellow liquid
Occurrence
Of the three possible isomers of n-valeric acid, only isovaleric acid has extensive application in flavoring;
originally reported in seal and dolphin fat; subsequently isolated from valerian. Also reported found in the essential oils of cypress,
citronella, laurel leaves, cajeput, Cymbopogon javanensis, hops, Persea pubescens, geranium, American peppermint, spearmint,
rosemary, lemongrass, Eucalyptus goniocalyx and other spp., tobacco, Monarda fistulos, Thymus mastichina, Artemisia frigida,
and probably in lavender; reported among the constituents of petitgrain lemon. Also reported found in many foods including apple,
currants, guava, grapes, papaya, peach, pineapple, raspberry, strawberry, potato, bell pepper, vinegar, breads, many cheeses, fish,
chicken, lamb, hop oil, beer, cognac, whiskies, cider, sherry, grape wines, rum, cocoa, tea, coffee, honey, soybean, passion fruit,
mushrooms, marjoram, plum, brandy, starfruit, trassi, rice, jackfruit, sake, sukiyaki, buckwheat, corn oil, cashew apple, malt, wort,
Bourbon vanilla, shrimp, mussels, cherimoya, Cape gooseberry and Chinese quince frui
Uses
Different sources of media describe the Uses of 503-74-2 differently. You can refer to the following data:
1. Isovaleric acid is used extensively as a flavoring ingredient in
nonalcoholic beverages and in foods such as ice cream,
candy, baked goods, and cheese, as a fragrance ingredient
in perfumes, and as a chemical intermediate in the
manufacture of sedatives and other pharmaceutical products.
It is also used as an extractant of mercaptans from petroleum
hydrocarbons, a vinyl stabilizer, and as an intermediate in the
manufacture of plasticizers and synthetic lubricants.
2. A molecular entity capable of donating a hydron to an acceptor (Bronsted base). It is a favorable carbon source for cell growth. Moreover, it is a promising odor indicator.
3. In flavors, perfumes, manufacture of sedatives.
Definition
ChEBI: A C5, branched-chain saturated fatty acid.
Preparation
By oxidation of isoamyl alcohol or isovaleric aldehyde
Aroma threshold values
Detection: 190 ppb to 2.8 ppm
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 30, p. 2787, 1982 DOI: 10.1248/cpb.30.2787Tetrahedron Letters, 23, p. 3135, 1982 DOI: 10.1016/S0040-4039(00)88578-0
General Description
Isovaleric acid is a colorless liquid with a penetrating odor. Isovaleric acid is slightly soluble in water. Isovaleric acid is corrosive to metals and to tissue.
Air & Water Reactions
Isovaleric acid is slightly soluble in water.
Reactivity Profile
Isovaleric acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Isovaleric acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Hazard
Strong irritant to tissue.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Check Digit Verification of cas no
The CAS Registry Mumber 503-74-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 3 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 503-74:
(5*5)+(4*0)+(3*3)+(2*7)+(1*4)=52
52 % 10 = 2
So 503-74-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)/p-1
503-74-2Relevant articles and documents
Seshadri et al.
, p. 1883 (1967)
Kinetics and mechanism of oxidation of L-leucine by alkaline diperiodatocuprate(III). A free radical intervention, deamination and decarboxylation
Naik, Keerti M.,Nandibewoor, Sharanappa T.
, p. 809 - 819 (2012)
The kinetics of oxidation of L-leucine by diperiodatocuprate (III) (DPC) in aqueous alkaline medium at a constant ionic strength of 0.10mol dm-3 was studied spectrophotometrically. The reaction between L-leucine and DPC in alkaline medium exhibits 1:4 stoichiometry (L-leucine: DPC). The reaction is of first order in [DPC] and has less than unit order in both [L-leucine] and [alkali]. However, the order in [Lleucine] and [alkali] changes from first order to zero order as their concentration increase. Intervention of free radicals was observed in the reaction. Increase in periodate concentration decreased the rate. The oxidation reaction in alkaline medium has been shown to proceed via a monoperiodatocuprate (III) - L-leucine complex, which decomposed slowly in a rate-determining step followed by other fast steps to give the products. The main oxidative products were identified by spot test and GC-MS. The reaction constants involved in the different steps of the mechanism were calculated. Indian Academy of Sciences.
Richardson,Fortey
, p. 1352 (1896)
-
Penfold,Simonsen
, p. 412,414 (1940)
-
Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process
Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun
supporting information, p. 2020 - 2024 (2022/03/31)
A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.
Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound
-
Paragraph 0172; 0175-0176; 0182; 0185-0186; 0192; 0195-0196, (2020/05/02)
Provided are: a method for producing an aliphatic carboxylic acid compound safely and easily from a starting material that can be obtained or produced industrially without generating a harmful substance such as haloform; and a pyridine compound adduct of an aliphatic ketone compound. The method for producing an aliphatic carboxylic acid compound is a method for producing an aliphatic carboxylic acid compound represented by Formula (I), and comprises: a first step for obtaining a pyridine compound adduct by adding a pyridine compound to an aliphatic ketone compound having an alpha-methyl groupin the presence of an oxidizing agent; and a second step of hydrolyzing the pyridine compound adduct in the presence of a base. In the Formula, R1 represents a substituted or unsubstituted linear alkyl group having 4-8 carbon atoms or a substituted or unsubstituted branched alkyl group having 4-8 carbon atoms; M represents hydrogen, a metal belonging to Group 1 or Group 2 of the periodic table, amethyl group, an ethyl group, an n-propyl group or an isopropyl group.
Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation
Sang, Rui,Kucmierczyk, Peter,Dühren, Ricarda,Razzaq, Rauf,Dong, Kaiwu,Liu, Jie,Franke, Robert,Jackstell, Ralf,Beller, Matthias
supporting information, p. 14365 - 14373 (2019/09/06)
The synthesis of carboxylic acids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers, cosmetics, pharmaceuticals, agrochemicals, and other manufactured chemicals. Although hydroxycarbonylations of olefins have been known for more than 60 years, currently known catalyst systems for this transformation do not fulfill industrial requirements, for example, stability. Presented herein for the first time is an aqueous-phase protocol that allows conversion of various olefins, including sterically hindered and demanding tetra-, tri-, and 1,1-disubstituted systems, as well as terminal alkenes, into the corresponding carboxylic acids in excellent yields. The outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key-to-success is the use of a built-in-base ligand under acidic aqueous conditions. This catalytic system is expected to provide a basis for new cost-competitive processes for the industrial production of carboxylic acids.
