ISOVALERALDEHYDE

Isovaleraldehyde has a choking, powerful, acrid, pungent, apple-like odor. 
Isovaleraldehyde is also reported to have a fruity, fatty, animal, almond odor.
Isovaleraldehyde is a colorless, low-solubility liquid with a pungent odor similar to that of apples.

CAS Number: 590-86-3
Molecular Formula: C5H10O
Molecular Weight: 86.13
EINECS Number: 209-691-5

Synonyms: 3-Methylbutanal, ISOVALERALDEHYDE, 590-86-3, 3-Methylbutyraldehyde, Isovaleral, Isopentaldehyde, Isoamylaldehyde, Butanal, 3-methyl-, Isovalerylaldehyde, Isopentanal, Isovaleric aldehyde, beta-Methylbutanal, Isoamyl aldehyde, 1-Butanal, 3-methyl-, Butyraldehyde, 3-methyl-, FEMA No. 2692, Aldehyde isovalerianique, DTXSID1021619, CHEBI:16638, 69931RWI96, NSC-404119, DTXCID201619, 209-691-5, Iso-Valeraldehyde, 2-Methylbutanal-4, 3-Methyl-1-butanal, iso-C4H9CHO, Butanal, methyl-, 3-Methyl-Butanal, 3-Methylbutan-1-al, 3-Methyl butyraldehyde, 3-methyl-Butyraldehyde, NSC 404119, MFCD00007014, .beta.-Methylbutanal, CHEMBL18360, 26140-47-6, 3-Methylbutylaldehyde, beta-Methylbutyraldehyde, 3-methyl butanal, CCRIS 2945, HSDB 628, 3-Methylbutyraldehyde (natural), Aldehyde isovalerianique [French], EINECS 209-691-5, BRN 0773692, b-Methylbutanal, Methyl butanal, AI3-16106, isovaler aldehyde, UNII-69931RWI96, Bortezomib Impurity23, Isovaleraldehyde, 97%, ISOVALERIC-ALDEHYDE, EC 209-691-5, SCHEMBL16240, SCHEMBL42915, ISOVALERALDEHYDE [MI], 4-01-00-03291 (Beilstein Handbook Reference), SCHEMBL920173, ISOVALERALDEHYDE [HSDB], SCHEMBL3238737, SCHEMBL3955196, SCHEMBL4345084, SCHEMBL9021651, WLN: VH1Y1&1, 3-METHYL BUTANAL [FCC], Isovaleraldehyde, >=97%, FG, SCHEMBL10789600, SCHEMBL28216701, STR03918, Isovaleraldehyde, analytical standard, Tox21_200891, 3-METHYLBUTYRALDEHYDE [FHFI], BBL027631, BDBM50028832, NSC404119, STL146355, AKOS000118930, Isovaleraldehyde, natural, >=95%, FG, NCGC00248867-01, NCGC00258445-01, CAS-590-86-3, FM140577, PD124039, I0192, NS00006828, EN300-18032, C07329, Q409554, F2190-0631, InChI=1/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H, ISOVALERALDEHYDE 97+%;ISOVALERALDEHYDE 95+% NATURAL;Isovaleraldehyde,98%;methylbutanal,3-methylbutanal;ISOVALERALDEHYDE(SG);Isoamylaldehyd;iso-C4H9CHO;Isovaleral

Isovaleraldehyde a methylbutanal that is butanal substituted by a methyl group at position 3. 
Isovaleraldehyde occurs as a volatile constituent in olives. It has a role as a flavouring agent, a plant metabolite, a volatile oil component and a Saccharomyces cerevisiae metabolite.
Isovaleraldehyde, formally 3-methylbutanal, is a pungent liquid that occurs in natural oils such as orange, lemon, peppermint, and eucalyptus. 

Isovaleraldehyde is also found in processed foods such as beer, cheese, and chocolate. 
Its odor has been described variously from “apple-like” to “suffocating”.
Inhalation of isovaleraldehyde carries additional considerations beyond its immediate irritant and flammability hazards, particularly in environments where exposure could be prolonged or poorly controlled.

One extended concern involves the interaction of its vapors with the respiratory tract. 
Even at moderate concentrations, Isovaleraldehyde can sensitize the airways, leading to an increased reactivity to other irritants in the environment. 
This heightened sensitivity may persist for hours or days, making exposed individuals more vulnerable to common airborne particles or pollutants. 

People with pre-existing conditions such as asthma, bronchitis, or chronic obstructive pulmonary disease (COPD) may experience exacerbated symptoms when exposed to even low levels of isovaleraldehyde vapors.
Another hazard arises from the volatile organic compound (VOC) nature of isovaleraldehyde. 
Being a reactive aldehyde, it can undergo atmospheric reactions, forming secondary irritants or contributing to the formation of ground-level ozone in poorly ventilated spaces.

This can indirectly create an environment where respiratory stress is heightened not only by the compound itself but also by its degradation products.
During industrial processes, isovaleraldehyde poses the risk of accidental releases, particularly when handled in large quantities or under pressure.
Uncontrolled release can lead to high vapor concentrations, which may quickly exceed safe exposure limits. 

This scenario is dangerous not only for workers but also for nearby populations if adequate containment systems are not in place. 
Emergency plans should include spill response protocols, vapor suppression strategies, and evacuation procedures for severe incidents.
Inhalation of isovaleraldehyde (also known as 3‑methylbutanal) presents several health and safety risks, especially in environments where its vapors are concentrated or during accidental exposure.

Isovaleraldehyde is a highly flammable liquid with a low flash point, meaning it can easily ignite even at relatively low temperatures. 
Its vapors are denser than air, which allows them to accumulate in low-lying areas and travel along surfaces where they can reach ignition sources. Under certain conditions, such as confinement with heat or sparks, the vapors may cause explosions.
Breathing in the vapors of isovaleraldehyde can lead to immediate irritation of the respiratory tract. 

Symptoms may include coughing, throat discomfort, chest tightness, nausea, headaches, and dizziness. 
In cases of significant exposure, it may trigger asthma-like responses, sometimes referred to as reactive airways dysfunction syndrome (RADS), where breathing difficulties may persist even after exposure has ended.
Direct contact with the skin can cause irritation, redness, and possible allergic reactions with repeated or prolonged exposure. 

The vapors or liquid form can also strongly irritate the eyes, leading to symptoms such as pain, tearing, and blurred vision. 
These effects require immediate washing and medical attention if symptoms persist.
Isovaleraldehyde has relatively low systemic toxicity, meaning that it is not highly poisonous in small amounts. 

However, inhaling high concentrations can still lead to harmful effects due to local irritation of the respiratory system. 
Its unpleasant odor and irritant properties typically discourage prolonged exposure, limiting the risk of severe systemic absorption.
Long-term data on isovaleraldehyde exposure is limited, but available evidence suggests that it is not likely to cause chronic diseases under normal conditions. 

Isovaleraldehyde is not considered to be genotoxic or carcinogenic. 
However, repeated irritation of the respiratory tract or skin may increase sensitivity over time.

Isovaleraldehyde is harmful to aquatic organisms and can have lasting effects on water ecosystems. 
Therefore, spills must be carefully controlled to prevent environmental contamination.

Melting point: -60 °C
Boiling point: 90 °C (lit.)
Density: 0.803 g/mL at 25 °C (lit.)
Vapor density: 2.96 (vs air)
Vapor pressure: 30 mm Hg (20 °C)
Refractive index: n20/D 1.388 (lit.)
FEMA: 2692 | 3-Methylbutyraldehyde
Flash point: 29 °F
Storage temp.: 2–8 °C
Solubility: Alcohol: miscible; soluble in propylene glycol and oils
Form: Liquid
Specific Gravity: 0.80
Color: Clear colorless to light yellow
Odor: At 0.10% in dipropylene glycol – ethereal, aldehydic, chocolate, peach, fatty
Odor Type: Aldehydic
Odor Threshold: 0.0001 ppm
Biological source: Synthetic
Explosive limit: 1.7–6.8% (V)
Water Solubility: 15 g/L (20 °C)
Merck: 14,5229
JECFA Number: 258
BRN: 773692
Stability: Stable, but light- and air-sensitive. Highly flammable. Readily forms explosive mixtures with air. Incompatible with strong oxidizing agents, bases, reducing agents, and air.
InChIKey: YGHRJJRRZDOVPD-UHFFFAOYSA-N
LogP: 1.5 at 25 °C and pH 7

Reported found in over 180 natural sources including apple, banana, berries, grapes, peach, papaya, peach, kohlrabi, carrot, celery, leek, peas, potato, bell pepper, tomato, ginger, peppermint and spearmint oil, other Mentha oils, vinegar, breads, many cheeses, butter, milk, egg, fatty and lean fish, meats, hop oil, beer, cognac, sherry, rum, grape wines, cocoa, coffee, tea, filberts, peanuts, pecans, peanut butter, barley, oats, soybean, honey, avocado, mace, plum, beans, mushrooms, starfruit, mango, beetroot, cardamom, coriander seed, rice, lovage leaf, pumpkin, buckwheat, laurel, malt, clary sage, wort, elderberry, clam, scallops, crab, crayfish, okra, sapodilla, truffles, kiwifruit and other sources.

Isovaleraldehyde colorless liquid with a weak suffocating odor.
Produces an irritating vapor. 
Isovaleraldehyde is a metabolite found in or produced by Saccharomyces cerevisiae.

Isovaleraldehyde is an aldehyde.
Aldehydes are frequently involved in self-condensation or polymerization reactions. 
These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. 

Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. 
Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. 
These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). 

The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.
Inhalation of Isovaleraldehyde, while not usually life-threatening at low exposure levels, can still cause severe irritation and discomfort. 
The compound’s flammability, local irritant effects, and environmental risks require careful handling, proper storage, and effective safety measures. 

When managed under controlled conditions, its hazards are significantly minimized, but vigilance is essential to ensure both worker and environmental safety.
There is also a potential hazard associated with thermal decomposition. 
When isovaleraldehyde is exposed to extreme heat, such as during a fire, it may decompose and release toxic gases like carbon monoxide and various aldehyde fragments. 

These gases are far more hazardous than the compound itself and can complicate firefighting efforts. 
For this reason, only specialized firefighting techniques and protective gear are recommended in scenarios where fires involve isovaleraldehyde.
From a storage perspective, improper handling can create hazardous conditions. 
Containers must be tightly sealed to prevent vapor leaks, and they must be stored in cool, well-ventilated areas away from oxidizers, acids, and ignition sources. 

Over time, if containers are not properly maintained, the aldehyde may undergo oxidation, forming peroxides or other reactive species that add to the risk profile. 
Therefore, regular inspection of storage facilities and periodic quality checks of the chemical are essential.

In occupational settings, cumulative low-level exposure can also present subtler hazards. Workers exposed repeatedly to vapors may experience ongoing irritation of mucous membranes, leading to chronic symptoms such as persistent sore throat, dry cough, or mild headaches. 
Although systemic toxicity is low, these symptoms can reduce work performance and overall quality of life if not managed properly. 
Rotating tasks, ensuring exposure stays below recommended thresholds, and implementing continuous air monitoring are practical preventive measures.

Strong odors, like those associated with aldehydes, can induce discomfort, anxiety, or nausea even at concentrations below hazardous thresholds. 
This aversive response can indirectly affect workplace safety by increasing stress and reducing concentration during critical tasks.

In summary, while the immediate hazards of isovaleraldehyde involve its strong irritant properties and high flammability, a broader view shows that it also carries risks related to airway sensitization, secondary atmospheric reactions, accidental releases, thermal decomposition byproducts, and chronic low-level exposure. 
Proper handling, storage, engineering controls, and comprehensive safety protocols are essential to minimize these risks and ensure safe use of the compound in any environment.

Uses Of Isovaleraldehyde:
Isovaleraldehyde is manufactured by oxidizing isoamyl alcohol with sodium perchromate and sulfuric acid. 
Isovaleraldehyde is present in essential oils of orange, peppermint, lemon, and other plants and fruits. 
Its main uses are as an artificial flavor additive and in perfumes.

Isovaleraldehyde acts as a reagent in the preparation of active pharmaceutical ingredient (API) products. 
It serves as an internal standard for the determination of wine aroma carbonyl compounds with 5-8 carbon atoms. 
Further, it is utilized as a standard to evaluate the quality of olive oils by headspace solid-phase microextraction-gas chromatography using flame ionization detection and multivariate analysis. 

In addition to this, it is employed to enhance the taste and odor of the food.
Isovaleraldehyde (3-methylbutanal) has a range of industrial, chemical, and research applications, and its uses extend across multiple sectors because of its unique chemical properties as an aldehyde with a branched-chain structure. 
It serves as an important intermediate in organic synthesis, a building block in fragrance and flavor industries, and a component in the manufacture of specialized chemicals. 

Its uses can be explained in more detail as follows:
One of the primary uses of isovaleraldehyde is as a starting material or intermediate in the production of various chemical compounds. 
Its reactive aldehyde functional group allows it to undergo numerous organic reactions, such as condensation, reduction, and oxidation. 

In industrial chemistry, it is commonly used in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. 
For example, it can be converted into isovaleric acid, which is further used in the production of drugs, esters, and synthetic lubricants. 
Additionally, it can be utilized in producing heterocyclic compounds that serve as precursors for medicinal formulations or advanced materials.

Isovaleraldehyde has a distinct, pungent odor often described as malty, fruity, or reminiscent of chocolate when diluted, and for this reason, it is extensively used as a flavoring agent in the food and beverage industry. 
Isovaleraldehyde contributes to the aroma profile of products such as chocolates, baked goods, beers, and other fermented foods. 
Its flavor characteristics are especially valuable in formulations where a malty or nutty note is desired. 

Moreover, it serves as an intermediate for producing other fragrance ingredients, such as isovaleric acid esters, which are widely used in perfumes, cosmetics, and household products.
Isovaleraldehyde acts as an essential building block in the synthesis of certain pharmaceuticals. 

Isovaleraldehyde is used to prepare intermediates for active pharmaceutical ingredients (APIs) and various biologically active compounds. 
Its chemical structure allows it to participate in reactions forming new carbon–carbon bonds, which are important in creating complex drug molecules. 
Furthermore, it is employed in the production of vitamin derivatives and compounds with sedative or anticonvulsant properties.

Isovaleraldehyde is also utilized in the agrochemical sector, where it serves as a raw material for synthesizing pesticides, herbicides, and plant growth regulators. 
Its reactivity enables the creation of chemical structures that exhibit biological activity against pests or help regulate plant metabolism. 
By modifying its structure, chemists can design new compounds with specific agricultural applications.

Isovaleraldehyde finds applications in the chemical industry for the production of plasticizers and resins. 
Through chemical transformations, it can be used to create intermediates that are incorporated into alkyd resins, which are widely used in paints, coatings, and adhesives. 
These materials benefit from the flexibility and chemical stability imparted by the aldehyde-derived intermediates.

Through hydrogenation, isovaleraldehyde can be converted into isopentyl alcohols, which themselves have uses as solvents, flavoring agents, and intermediates for other chemicals. 
Additionally, through reductive amination, it can form amines that are valuable in pharmaceuticals, dyes, and other specialty applications. 
These transformations highlight its versatility in chemical manufacturing.

In laboratory settings, isovaleraldehyde is frequently used as a reagent for various organic chemistry experiments. 
Isovaleraldehyde serves as a model compound in studying aldehyde reactivity, condensation reactions (such as aldol condensations), and the synthesis of branched-chain compounds.
It is also employed in analytical chemistry to develop methods for detecting and quantifying volatile aldehydes in environmental or industrial samples.

Interestingly, isovaleraldehyde is a naturally occurring compound found in certain foods and beverages, particularly those involving fermentation, such as beer, whiskey, and wine. 
In these contexts, it contributes to the aroma profile but is usually present only in trace amounts. 
In food technology, synthetic isovaleraldehyde is sometimes added in controlled quantities to enhance flavors, particularly in chocolate, nut, and malt-flavored products.

Isovaleraldehyde’s branched structure makes it valuable in the synthesis of fine chemicals where steric effects are important. 
Isovaleraldehyde can be used to design molecules with specific physical and chemical properties required for advanced materials, coatings, or catalysts.

Isovaleraldehyde is a multifunctional chemical with applications ranging from industrial manufacturing to fine chemical synthesis. 
Isovaleraldehyde serves as a key intermediate in the production of pharmaceuticals, agrochemicals, fragrances, flavors, plasticizers, and advanced materials.

Its presence in food and beverages further broadens its relevance beyond industrial use. 
Despite its beneficial applications, careful handling and strict safety controls are essential due to its irritant properties, volatility, and flammability.

Safety Profile Of Isovaleraldehyde:
Inhalation causes chest discomfort, nausea, vomiting, and headache. 
Contact of liquid with eyes or skin causes irritation. 
Ingestion causes irritation of mouth and stomach.

Because of its hazards, strict safety controls are necessary when handling isovaleraldehyde. 
Workplaces should use proper ventilation to avoid the accumulation of vapors, and equipment should be designed to prevent static discharge or sparks. 
Personal protective equipment, such as gloves, eye protection, and organic vapor respirators, should be used during handling.

Move the affected individual to fresh air and allow them to rest; seek medical help if symptoms do not subside.
Wash thoroughly with water and remove contaminated clothing; get medical advice if irritation continues.
Rinse eyes with plenty of water for several minutes and obtain medical assistance if discomfort persists.

Isovaleraldehyde is a highly flammable liquid with a low flash point, meaning it can easily catch fire when exposed to heat, open flames, or sparks. 
Its vapors are heavier than air, allowing them to travel along surfaces and accumulate in low areas where they can ignite unexpectedly. 
In confined spaces, this can lead to explosive vapor–air mixtures. 

Containers exposed to heat may rupture, releasing flammable vapors that intensify fire hazards.
The inhalation of isovaleraldehyde vapors is one of the primary risks associated with this compound. 
Breathing in its fumes can cause irritation of the respiratory tract, leading to symptoms such as coughing, throat irritation, chest tightness, nausea, dizziness, and headaches. 

In cases of high exposure, it can trigger asthma-like reactions or reactive airway dysfunction syndrome (RADS), which may persist for days even after exposure stops. 
Prolonged inhalation of high concentrations can impair lung function and cause systemic discomfort.

Direct contact with isovaleraldehyde can lead to skin irritation, redness, and itching. 
Prolonged or repeated contact may result in dermatitis or allergic skin reactions in sensitive individuals. 

Contact with the eyes causes painful irritation, tearing, redness, and blurred vision. 
Immediate washing is necessary to prevent further damage, and medical attention may be required in severe cases.