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Home> Encyclopedia >   /  Food Additives  /  Pharmaceutical Intermediates  /  Organic Intermediate  /  Essential oils and others  /  Flavour & Fragrance
Isovaleric acid structure
Isovaleric acid structure

Isovaleric acid

Iupac Name:3-methylbutanoic acid
CAS No.:503-74-2
Molecular Weight:102.1317
Introduction: Isovaleric acid has a characteristic disagreeable odor. It is extremelypenetrating and persistent with a sour taste. May be synthesized by oxidation of isoamyl alcohol or isovaleric aldehyde. View more+
1. Names and Identifiers
1.1 Name
Isovaleric acid
1.2 Synonyms

1,1-DIMETHYLPROPYL 3-METHYLBUTANOATE 2-Isovalerylamino-naphthalin 3-methyl butyric acid 3-METHYLBUTANOIC ACID 3-methyl-butanoic acid,1,1-dimethylpropyl ester 3-Methylbutanoic acid,3-Methylbutyric acid 3-Methylbuttersαure 3-methylbutyrate 3-METHYLBUTYRIC ACID 3-methyl-butyricaci 3-Methyl-n-butyric acid 3-Methyl-n-butyricacid AKOS BBS-00003796 Butanoic acid, 3-methyl- Butanoic acid,3-methyl-,1,1-dimethylpropyl ester EINECS 207-975-3 i-butanoic acid isobutanoic acid Isovaleriansaeure-tert-pentylester iso-valeric acid MFCD00002726 QV1Y1&1 RARECHEM AL BO 0154 tert-Amyl isovalerate tert-Pentyl alcohol,isovalerate Β-methylbutyric acid

1.3 CAS No.
503-74-2
1.4 CID
10430
1.5 EINECS(EC#)
207-975-3
1.6 Molecular Formula
C5H10O2 (isomer)
1.7 Inchi
InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
1.8 InChkey
GWYFCOCPABKNJV-UHFFFAOYSA-N
1.9 Canonical Smiles
CC(C)CC(=O)O
1.10 Isomers Smiles
CC(C)CC(=O)O
2. Properties
3.1 Density
0.926
3.1 Melting point
-35℃
3.1 Boiling point
176℃
3.1 Refractive index
1.399-1.407
3.1 Flash Point
70℃
3.1 Vapour pressure
0.44 mmHg
3.1 Precise Quality
102.06800
3.1 PSA
37.30000
3.1 logP
1.11710
3.1 Solubility
48g/l
3.2 Appearance
colorless to yellowish transparent liquid.
3.3 Chemical Properties
Isovaleric acid has a characteristic disagreeable, rancid, cheese-like odor. It is extremely penetrating and persistent witha 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
3.4 Color/Form
Colorless liquid
3.5 Decomposition
When heated to decomposition it emits acrid smoke and fumes.
3.6 Heat of Vaporization
12,951.1 GCAL/GMOL
3.7 HenrysLawConstant
8.33e-07 atm-m3/mole
3.8 Odor
DISAGREEABLE, RANCID-CHEESE ODOR
3.9 PH
3.1 (10g/l, H2O, 25℃)
3.10 pKa
4.77(at 25℃)
3.11 Water Solubility
25 g/L (20 oC)
3.12 Spectral Properties
IR: 1835 (Sadtler Research Laboratories Prism Collection)
NMR: 16007 (Sadtler Research Laboratories Spectral Collection)
MASS: 276 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Index of refraction = 1.4033 at 20 deg C/D
3.13 StorageTemp
Store below +30°C.
3. Use and Manufacturing
4.1 Definition
ChEBI: A C5, branched-chain saturated fatty acid.
4.2 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. Isovaleric acid Preparation Products And Raw materials Preparation Products
4.3 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.
4.4 Storage
Ambient temperatures.
4.5 Usage
Isovaleric acid is used extensively as a flavoring ingredient innonalcoholic beverages and in foods such as ice cream,candy, baked goods, and cheese, as a fragrance ingredientin perfumes, and as a chemical intermediate in themanufacture of sedatives and other pharmaceutical products.It is also used as an extractant of mercaptans from petroleumhydrocarbons, a vinyl stabilizer, and as an intermediate in themanufacture of plasticizers and synthetic lubricants.
4. Safety and Handling
5.1 Symbol
GHS05
5.1 Hazard Codes
C; T
5.1 Signal Word
Danger
5.1 Risk Statements
R22;R24;R34
5.1 Safety Statements
S26;S28;S36/37/39;S38;S45
5.1 Exposure Standards and Regulations
Isovaleric acid is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.
5.2 Packing Group
III
5.2 Octanol/Water Partition Coefficient
Log Kow = 1.16
5.3 Hazard Class
6.1
5.3 Hazard Declaration
H314
5.3 Cleanup Methods
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
5.4 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5.5 DOT Emergency Guidelines
/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Health: 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. /Corrosive liquid, NOS/
/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Fire or Explosion: 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. /Corrosive liquid, NOS/
/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Corrosive liquid, NOS/
/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Corrosive liquid, NOS/
/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Corrosive liquid, NOS/
/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. /Corrosive liquid, NOS/
/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. /Corrosive liquid, NOS/
/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Corrosive liquid, NOS/
5.6 RIDADR
UN 3265 8
5.6 Caution Statement
P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338
5.6 WGK Germany
1
5.6 RTECS
NY1400000
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin corrosion, Category 1B

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H314 Causes severe skin burns and eye damage

Precautionary statement(s)
Prevention

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P363 Wash contaminated clothing before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P310 Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Merck
14,5231
9.1 BRN
1098522
9.2 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.
9.3 Chemical Properties
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
9.4 Chemical Properties
clear colorless to slightly yellow liquid
9.5 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
9.6 Uses
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.
9.7 Uses
In flavors, perfumes, manufacture of sedatives.
9.8 Definition
ChEBI: A C5, branched-chain saturated fatty acid.
9.9 Preparation
By oxidation of isoamyl alcohol or isovaleric aldehyde
9.10 Aroma threshold values
Detection: 190 ppb to 2.8 ppm
9.11 Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 30, p. 2787, 1982 DOI: 10.1248/cpb.30.2787
Tetrahedron Letters, 23, p. 3135, 1982 DOI: 10.1016/S0040-4039(00)88578-0
9.12 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.
9.13 Air & Water Reactions
Isovaleric acid is slightly soluble in water.
9.14 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.
9.15 Hazard
Strong irritant to tissue.
9.16 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.
9.17 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.
9.18 Usage
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.
10. Computational chemical data
  • Molecular Weight:102.1317g/mol
  • Molecular Formula:C5H10O2
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:102.068079557
  • Monoisotopic Mass:102.068079557
  • Complexity:66.5
  • Rotatable Bond Count:2
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:2
  • Topological Polar Surface Area:37.3
  • Heavy Atom Count:7
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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