Quick Search
Isovaleraldehyde is used as a food flavoring additive.
Isovaleraldehyde's 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.
CAS Number: 590-86-3
EC Number: 209-691-5
Molecular Formula: C5H10O / (CH3)2CHCH2CHO
Molecular Weight: 86.13
SYNONYMS:
3-Methylbutanal, 3-Methylbutyraldehyde, NSC 404119, 3-METHYLBUTANAL,3-METHYLBUTYRALDEHYDE,Isovaleral,Butanal,3-methyl-,3-Methyl-1-butanal,ISOVALERIC ALDEHYDE,FEMA 2692,3-Methylbutan-1-al,3-Methybutanol,butanal,3-methyl, iso,amyl aldehyde, iso,amylaldehyde, butanal, 3-methyl-, 1-,butanal, 3-methyl-, 3-,methyl butan-1-al, 3-,methyl butanal, 3-,methyl butyraldehyde, 3-,methyl-1-butanal, 3-,methyl-butanal, 3-,methyl-butyraldehyde, 3-,methylbutan-1-al, 3-,methylbutanal, 3-,methylbutylaldehyde, 3-,methylbutyraldehyde, iso,pentaldehyde, iso,pentanal, iso,valeral, iso-,valeraldehyde, nat.iso,valeraldehyde, iso,valeraldehyde (natural), iso,valeraldehyde natural, iso,valeraldehyde synthetic, valeraldehyde(iso), iso,valeric aldehyde, iso,valerianic aldehyde, 3-Methylbutanal, Isovaleral, Isovaleric Aldehyde, 3-Methylbutanal, ISOVALERALDEHYDE, 590-86-3, 3-Methylbutyraldehyde, Isovaleral, Isopentaldehyde, Butanal, 3-methyl-, Isoamylaldehyde, Isopentanal, Isovalerylaldehyde, Isovaleric aldehyde, beta-Methylbutanal, Isoamyl aldehyde, 1-Butanal, 3-methyl-, Butyraldehyde, 3-methyl-, FEMA No. 2692, Aldehyde isovalerianique, DTXSID1021619, 69931RWI96, NSC-404119, DTXCID201619, CHEBI:16638, RefChem:40317, 209-691-5, Iso-Valeraldehyde, 2-Methylbutanal-4, 3-Methyl-1-butanal, 3-Methyl-Butanal, iso-C4H9CHO, 3-methyl butanal, Butanal, methyl-, 3-Methylbutan-1-al, 3-Methyl butyraldehyde, NSC 404119, .beta.-Methylbutanal, 3-methyl-Butyraldehyde, MFCD00007014, CHEMBL18360, 26140-47-6, 3-Methylbutylaldehyde, beta-Methylbutyraldehyde, 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], BDBM50028832, MSK158402, NSC404119, AKOS000118930, EBC-613096, Isovaleraldehyde, natural, >=95%, FG, NCGC00248867-01, NCGC00258445-01, CAS-590-86-3, FM140577, PD124039, I0192, NS00006828, EN300-18032, C07329, F094970, Q409554, F2190-0631, InChI=1/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H, Isovaleraldehyde, β-Methylbutanal, Isopentanal, Isovaleral, Isovaleric aldehyde, Isovalerylaldehyde, 3-Methylbutan-1-al, 3-Methylbutanal, 3-Methylbutyraldehyde, iso-C4H9CHO, Butyraldehyde, 3-methyl-, Isoamylaldehyde, Isopentaldehyde, 1-Butanal, 3-methyl-, 2-Methylbutanal-4, 3-Methyl-1-butanal, NSC 404119, 3-Methylbutanal, 3-Methylbutyraldehyde, Isovaleraldehyde, 3-Methyl-1-butanal, Isoamylaldehyde, Isopentanal, Isovaleral, Isovaleric Aldehyde, β-Methylbutanal, 3-Methylbutanal, 3-Methylbutyraldehyde, Isoamyl aldehyde, Isopentaldehyde, Isovaleral, Isovaleric aldehyde, ISOVALERALDEHYDE 97+%, ISOVALERALDEHYDE 95+% NATURAL, Isovaleraldehyde,98%, methylbutanal,3-methylbutanal, ISOVALERALDEHYDE(SG), Isoamylaldehyd, iso-C4H9CHO, Isovaleraldehyd, Isovaleraldehyde, 3-Methylbutanal, Isopentanal, Isopentyl aldehyde, Isobutylacetaldehyde, 3-Methylbutyraldehyde, β-Methylbutyraldehyde, Isovaleric aldehyde
Isovaleraldehyde is a branched-chain aliphatic aldehyde with the molecular formula C₅H₁₀O.
Isovaleraldehyde is a colorless, highly volatile liquid characterized by a penetrating malty, chocolate-like, fermented, and fruity odor.
Naturally occurring in various foods such as cocoa, coffee, cheese, malt, beer, wine, and fermented products, Isovaleraldehyde is an important aroma compound in the flavor and fragrance industries.
Isovaleraldehyde is a colorless liquid with a weak suffocating odor.
Isovaleraldehyde floats on water.
Isovaleraldehyde is a metabolite found in or produced by Saccharomyces cerevisiae.
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.
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.
Isovaleraldehyde is a methylbutanal that is butanal substituted by a methyl group at position 3.
Isovaleraldehyde occurs as a volatile constituent in olives.
Isovaleraldehyde has a role as a flavouring agent, a plant metabolite, a volatile oil component and a Saccharomyces cerevisiae metabolite.
Isovaleraldehyde is a colorless liquid with a weak suffocating odor.
Isovaleraldehyde floats on water.
Isovaleraldehyde is a methylbutanal that is butanal substituted by a methyl group at position 3.
Isovaleraldehyde occurs as a volatile constituent in olives.
Isovaleraldehyde has a role as a volatile oil component, a flavouring agent, a Saccharomyces cerevisiae metabolite and a plant metabolite.
Isovaleraldehyde has been reported in Eucalyptus pulverulenta, Tuber melanosporum, and other organisms with data available.
Isovaleraldehydel is a metabolite found in or produced by Saccharomyces cerevisiae.
Isovaleraldehyde, formerly 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.
Isovaleraldehyde's odor has been described variously from “apple-like” to “suffocating”.
In addition to its natural sources, Isovaleraldehyde can be synthesized in several ways, including the oxidation of isoamyl alcohol with Na2Cr2O7 and H2SO4, the hydroformylation of isobutene, the isomerization of 3-methyl-3-butene-1-ol catalyzed by CuO–ZnO, and the reaction between isobutene and formaldehyde.
Isovaleraldehyde’s strong aroma makes it useful (in small amounts) as a perfume component.
Isovaleraldehyde organic compound, also known as 3-methylbutanal, with the formula (CH3)2CHCH2CHO.
Isovaleraldehyde is an aldehyde, a colorless liquid at STP, and found in low concentrations in many types of food.
Isovaleraldehyde is a common reagent or building block in organic synthesis.
Acid-catalyzed cyclic trimerization of Isovaleraldehyde gives 2,4,6-Triisobutyl-1,3,5-trioxane [68165-40-2].
This is a flavouring agent, Isovaleraldehyde, that can be used in confectionary, tobacco, and other foodstuffs, toothpastes and the like.
Isovaleraldehyde is described as imparting a creamy, dairy, vanilla chocolate and berry flavour.
Isovaleraldehyde is a versatile chemical compound recognized for its distinct fruity aroma and is widely used in the flavor and fragrance industries.
Isovaleraldehyde, also known as 3-methylbutanal, serves as a key ingredient in the formulation of various food flavors and perfumes, enhancing sensory experiences with its pleasant scent.
Its unique properties allow Isovaleraldehyde to act as a building block in organic synthesis, making it valuable in the production of pharmaceuticals and agrochemicals.
Researchers appreciate Isovaleraldehyde for its ability to participate in various chemical reactions, including aldol condensations and Michael additions, which are essential in developing more complex molecules.
In addition to its applications in flavoring and fragrance, Isovaleraldehyde is utilized in the production of polymers and resins, contributing to the development of high-performance materials.
Its relatively low toxicity and favorable safety profile make Isovaleraldehyde an attractive choice for manufacturers seeking effective and safe chemical solutions.
With its broad range of applications and beneficial properties, Isovaleraldehyde stands out as a crucial compound for professionals in the food, fragrance, and chemical industries.
Isovaleraldehyde is a chemical compound belonging to the group of aldehydes.
Together with Isovaleraldehyde's isomeric compounds, valeraldehyde ( n -pentanal), 2-methylbutyraldehyde, and pivalaldehyde, it forms the group of pentanals.
Isovaleraldehyde can be compared to Furfural, standing out thanks to its more pyrogenic and bitter almond gourmand note.
Isovaleraldehyde is more etheric and fruity-cherry and pear.
Isovaleraldehyde can be detected by absorption with a 2,4-dinitrophenylhydrazine-impregnated glass fiber filter, subsequent desorption with acetonitrile, followed by chromatographic determination by HPLC with a UV detector (365 nm).
Isovaleraldehyde organic compound, also known as 3-methylbutanal, with the formula (CH₃)₂CHCH₂CHO.
Isovaleraldehyde is an aldehyde, a colorless liquid at STP, and found in low concentrations in many types of food.
USES and APPLICATIONS of ISOVALERALDEHYDE:
Food Aroma Research uses of Isovaleraldehyde: Because Isovaleraldehyde naturally occurs in fermented foods, roasted coffee, cocoa, cheese, wine, beer, and certain fruits, researchers frequently use it to study aroma formation during Maillard reactions, fermentation, roasting, food aging, and flavor development.
Given that Isovaleraldehyde can be extracted from leucine, its presence is not limited to beer.
Isovaleraldehyde is found as a flavoring component in various foods, described as having a malty flavor, and is present in cheese, coffee, chicken, fish, chocolate, olive oil, and tea.
Isovaleraldehyde is used as a reactant in synthesizing various compounds.
Notably, Isovaleraldehyde is employed in synthesizing 2,3-dimethylbut-2-ene, which is then converted to 2,3-dimethylbutane-2,3-diol and methyl tert-butyl ketone, commonly known as mesotrione.
Mesotrione itself is used in the synthesis of numerous herbicides.
Additionally, a range of drugs, such as butethamine, are synthesized from Isovaleraldehyde and its corresponding acids.
Isovaleraldehyde is a common reagent or building block in organic synthesis.
Isovaleraldehyde undergoes cyclotrimerization under acidic conditions to yield 2,4,6-triisobutyl-1,3,5-trioxane.
Isovaleraldehyde is a flavoring agent used in candies, tobacco, and other foods, toothpaste, etc.
Isovaleraldehyde is claimed to impart creamy, dairy, vanilla-chocolate, and berry flavors.
Isovaleraldehyde is used as a food flavoring additive.
Isovaleraldehyde's 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.
Isovaleraldehyde serves as an internal standard for the determination of wine aroma carbonyl compounds with 5-8 carbon atoms.
Further, Isovaleraldehyde 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, Isovaleraldehyde is employed to enhance the taste and odor of the food.
Isovaleraldehyde is used in artificial flavors and perfumes.
Commercially, Isovaleraldehyde is used as a reagent for the production of pharmaceuticals, perfumes and pesticides.
Isovaleraldehyde is used as a reactant in the synthesis of a number of compounds.
Notably, Isovaleraldehyde is used to synthesize tetramethylethylene, and is then converted to pinacol and pinacolone.
Pinacolone itself is then used in synthesis for number of pesticides.
Additionally, a range of pharmaceuticals, such as butizide, are synthesized from isovaleraldehyde and its corresponding acid.
Isovaleraldehyde is used as a food flavorant additive.
Isovaleraldehyde can be produced commercially and is used as a reagent for the production of pharmaceuticals and pesticides.
Isovaleraldehyde, also known as 3-methylbutanal, is widely used in perfumes and cosmetics for its aromatic properties.
Isovaleraldehyde is used as an intermediate in the production of pharmaceuticals, vitamins, pesticides, solvents and plasticizers.
Isovaleraldehyde, as an important organic compound, finds widespread application in the flavor and fragrance industry due to its distinctive aromatic properties.
Its stability and excellent aroma effects make Isovaleraldehyde an indispensable component in many products.
Industrially, Isovaleraldehyde serves as a valuable intermediate for synthesizing pharmaceuticals, fragrances, flavoring agents, resins, plastic additives, and specialty organic chemicals.
Due to its reactive aldehyde functional group, Isovaleraldehyde readily participates in oxidation, reduction, condensation, and Schiff base formation reactions.
-Flavor Industry uses of Isovaleraldehyde:
Isovaleraldehyde is widely used as a flavoring substance because it contributes pleasant malty, cocoa-like, chocolate, biscuit, caramel, and fermented notes.
Isovaleraldehyde is commonly incorporated into: chocolate flavors, coffee flavors, baked goods, dairy flavors, malt beverages, confectionery products, savory food formulations.
Even extremely small concentrations can significantly influence the overall aroma profile of foods.
-Fragrance Industry uses of Isovaleraldehyde:
Isovaleraldehyde is used in perfume compositions where warm, malty, cocoa-like, and nutty notes are desired.
Isovaleraldehyde appears in: gourmand fragrances, tobacco accords, leather fragrances, woody compositions, cosmetic fragrances.
-Chemical Intermediate uses of Isovaleraldehyde:
One of Isovaleraldehyde's most important industrial roles is serving as an intermediate for manufacturing: pharmaceuticals, agricultural chemicals, fragrance molecules, specialty aldehydes, fine chemicals, plastic additives, resin modifiers.
Isovaleraldehyde's aldehyde functionality allows efficient conversion into numerous higher-value compounds.
-Organic Synthesis uses of Isovaleraldehyde:
In laboratory chemistry, Isovaleraldehyde is frequently used for: aldol condensation reactions, Grignard reactions, reductive amination, acetal synthesis, Schiff base production, heterocyclic compound synthesis.
Its moderate molecular size and branched structure make Isovaleraldehyde particularly useful for preparing substituted organic molecules.
CHEMISTRY & USES of ISOVALERALDEHYDE:
Uses in perfumery:
Isovaleraldehyde is used in cherry and chocolate notes, to bring a liquorous head note.
Isovaleraldehyde is found in the odorous principle of many fruits and food we consume every day : apple, ginger, beef, lovage…
Isomerism:
Isovaleraldehyde does not have any isomer used in perfumery.
Synthesis precursor:
Isovaleraldehyde can be used to synthesize Schiff bases, reacting with Methyl Anthranilate or Indole for example.
Synthesis route:
Isovaleraldehyde is synthesized by oxydation of Isoamyl Alcohol.
Stability :
Isovaleraldehyde may form Schiff bases by reacting with Methyl Anthranilate or Indole for example, forming another colored and differently smelling compound.
BENEFITS of ISOVALERALDEHYDE:
Isovaleraldehyde offers several practical advantages across multiple industries.
Isovaleraldehyde's benefits include:
* excellent aroma potency,
* effective performance at very low concentrations,
* natural occurrence in many foods,
* versatility as a synthetic intermediate,
* relatively simple production,
* broad compatibility with organic solvents,
* usefulness in flavor optimization,
* importance in fragrance formulation.
INDUSTRIAL PRODUCTION of ISOVALERALDEHYDE:
Commercially, Isovaleraldehyde is typically produced through controlled oxidation or dehydrogenation of isoamyl alcohol (3-methyl-1-butanol).
Alternative production methods include catalytic oxidation processes designed to maximize aldehyde yield while minimizing further oxidation to isovaleric acid.
SCIENTIFIC INFORMATION ON ISOVALERALDEHYDE:
Isovaleraldehyde is naturally formed during amino acid metabolism, particularly from leucine.
Isovaleraldehyde is an important volatile organic compound contributing to food aroma complexity.
Isovaleraldehyde is frequently detected in roasted coffee and cocoa through Maillard chemistry.
Isovaleraldehyde is used as a reference compound in flavor chemistry research.
Reactive toward nucleophiles because of Isovaleraldehyde's electrophilic carbonyl carbon.
Isovaleraldehyde can polymerize under certain acidic conditions if improperly stored.
Isovaleraldehyde is compatible with many industrial organic solvents.
Isovaleraldehyde serves as a precursor for numerous specialty chemicals requiring branched carbon frameworks.
PREPARATION of ISOVALERALDEHYDE:
By oxidation of isoamyl alcohol.
REACTIVITY PROFILE of ISOVALERALDEHYDE:
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.
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.
OCCURRENCE of ISOVALERALDEHYDE:
Isovaleraldehyde is 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.
CHEMICAL BEHAVIOR of ISOVALERALDEHYDE:
The aldehyde group makes Isovaleraldehyde highly reactive in organic synthesis.
Isovaleraldehyde readily:
oxidizes to isovaleric acid,
reduces to isoamyl alcohol,
undergoes aldol condensation,
forms Schiff bases with primary amines,
reacts with alcohols to form acetals,
participates in nucleophilic addition reactions.
Isovaleraldehyde slowly oxidizes when exposed to atmospheric oxygen, making storage under tightly sealed conditions preferable.
CHARACTERISTICS of ISOVALERALDEHYDE:
Isovaleraldehyde possesses several properties that make it valuable in industrial and commercial applications.
Isovaleraldehyde is:
highly volatile,
strongly odor-active,
chemically reactive,
naturally occurring,
biodegradable,
useful as a synthetic building block,
effective in low concentrations for aroma production.
Its distinctive odor makes Isovaleraldehyde an important flavor and fragrance ingredient despite its relatively simple molecular structure.
HAPPEN of ISOVALERALDEHYDE:
Isovaleraldehyde occurs naturally in tea, acacia trees, camphor trees, lemongrass, lavender, tomatoes, apples, mints, peppermint, horsemint, wild bergamots, allspice, sandalwood, potatoes, germander, pennyroyal, corn, and ginger, among other things.
Isovaleraldehyde also contributes to the aroma of roasted coffee.
Isovaleraldehyde is also a component of the alarm pheromone of the wasp Vespula vulgaris.
EXTRACTION and PRESENTATION of ISOVALERALDEHYDE:
Isovaleraldehyde is produced by hydroformylation of isobutene.
In 2000, several thousand tons of Isovaleraldehyde were produced in Germany.
This means it is one of the isovaleraldehyde substances that are produced in large quantities (“High Production Volume Chemical”, HPVC) and for which the Organisation for Economic Co-operation and Development (OECD) has compiled a Screening Information Dataset (SIDS) on potential hazards.
CHARACTERISTICS of ISOVALERALDEHYDE:
Isovaleraldehyde is sensitive to light and air and has a viscosity of 0.58 mPa·s at 20 °C.
SAFETY-RELATED PARAMETERS of ISOVALERALDEHYDE:
Isovaleraldehyde has a flash point of −3 °C.
The ignition temperature of Isovaleraldehyde is 207 °C.
Isovaleraldehyde therefore falls into temperature class T3.
SYNTHESIS of ISOVALERALDEHYDE:
Synthetic routes for the production of Isovaleraldehyde vary.
One method is by the hydroformylation of isobutene:
(CH3)2C=CH2 + H2 + CO → (CH3)2CH−CH2CHO
A small amount of 2,2-dimethylpropanal ((CH3)2C(CHO)CH3) side product is also generated.
Another method of production involves the isomerization of isoprenol using CuO–ZnO as a catalyst.
A mixture of isoprenol and prenol may also be used.
These starting materials are obtained from a reaction between isobutene and formaldehyde:
CH3CH3CCH2 + CH2O → (CH3)2CHCH2CHO
Finally, in beer Isovaleraldehyde is produced via a reaction between the amino acid leucine and reductones in the malt.
OCCURRENCES and USES of ISOVALERALDEHYDE:
As it can be derived from leucine, the occurrence of Isovaleraldehyde is not limited to beer.
Isovaleraldehyde has found to be a flavor component in many different types of foods.
Isovaleraldehyde is described as having a malty flavor and has been found in cheese, coffee, chicken, fish, chocolate, olive oil, and tea.
PROPERTIES OF ISOVALERALDEHYDE:
Isovaleraldehyde is a colorless liquid at room temperature with several physical properties that are critical to its industrial applications and safety precautions.
What is the flash point of Isovaleraldehyde?
Here are some of the key properties:
(1) Isovaleraldehyde Color:
Clear colorless to pale yellow
(2) Isovaleraldehyde Smell:
Present in natural oils like orange, lemon, peppermint, and eucalyptus.
Also found in processed foods such as beer, cheese, and chocolate, Isovaleraldehyde exhibits a variety of descriptors from "apple-like" to "suffocating."
(3) Isovaleraldehyde Melting Point: -51°C (-60°F; 222K)
(4) Isovaleraldehyde Boiling Point: 92°C (198°F; 365K)
(5) Isovaleraldehyde Density: 0.785 g/mL at 20°C (lower than water)
(6) Isovaleraldehyde Vapor Density: 2.96 (air = 1)
(7) Isovaleraldehyde Vapor Pressure: 50 mmHg at 30°C
(8) Isovaleraldehyde Solubility:
Soluble in alcohols and ethers, slightly soluble in water
(9) Isovaleraldehyde Flash Point: 29°F
(10) Isovaleraldehyde Refractive Index n20/D 1.388 (lit.)
ISOVALERALDEHYDE STRUCTURE ANALYSIS:
Isovaleraldehyde features a five-carbon chain structure with the molecular formula (CH3)2CHCH2CHO.
Isovaleraldehyde includes a methyl group ((CH3)2) attached to the third carbon and terminates with an aldehyde group (CHO) at the chain end.
This structural arrangement of Isovaleraldehyde exhibits unique characteristics:
(1) Chirality:
The presence of the third carbon bonded to four different groups (two methyl groups, one hydrogen, and the remaining chain) makes Isovaleraldehyde a chiral molecule, existing in two non-superimposable mirror image forms.
(2) Polarity:
The carbonyl group introduces polarity within the molecule, resulting in low solubility in water.
By examining these aspects, the distinct properties and applications of Isovaleraldehyde in various industries are underscored, highlighting its role in fragrance creation and beyond.
PRODUCTION AND SYNTHESIS OF ISOVALERALDEHYDE:
Oxidation of Isoamyl Alcohol
Isoamyl alcohol, abundant and low-cost, is widely present as a byproduct in alcohol fermentation at distilleries and can be obtained by distillation.
Therefore, the oxidative dehydrogenation of isoamyl alcohol to produce Isovaleraldehyde is considered a relatively economical process.
(1) According to the "Chinese Chemical Commodity Encyclopedia," sulfuric acid and chromic acid can directly oxidize isoamyl alcohol to Isovaleraldehyde.
Researchers at Guangxi University, led by Li Jinglin, utilized Ag/KZSM-5 molecular sieves as catalysts to react isoamyl alcohol with air in specific proportions to obtain Isovaleraldehyde.
Additionally, Gao Hufei and colleagues developed a novel catalyst, Co-doped ZnO/MCM-41 molecular sieves, for the catalytic oxidation of isoamyl alcohol, although these methods are complex to operate, pose significant safety hazards, and suffer from low yields, making large-scale industrial production impractical.
(2) Recep Ozen developed a stable, easily storable, and low-cost chromium reagent, 3,4-dihydroisoquinoline trichloroacetic acid chromium, which, under non-protonic solvent and room temperature conditions, can effectively oxidize primary and secondary alcohols to carbonyl compounds, including aryl compounds.
Using this oxidant, oxidation of isoamyl alcohol yielded Isovaleraldehyde in just half an hour with a 90% yield.
Hydroformylation of Isobutene
Despite the maturation of processes for synthesizing Isovaleraldehyde from isoamyl alcohol, the starting material, isoamyl alcohol, often has low purity and contains impurities, necessitating purification before participation in reactions, thereby increasing production costs.
Therefore, the hydroformylation of isobutene to produce Isovaleraldehyde is more commonly employed in industry.
This reaction boasts atom economy, achieves zero emissions of waste, is highly efficient, energy-saving, and relatively safe.
PHYSICAL and CHEMICAL PROPERTIES of ISOVALERALDEHYDE:
Linear Formula: (CH3)2CHCH2CHO
CAS Number: 590-86-3
Molecular Weight: 86.13
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24848781
EC Number: 209-691-5
Beilstein/REAXYS Number: 773692
MDL number: MFCD00007014
Assay: 97%
Form: liquid
CBNumber: CB0351221
Molecular Formula: C5H10O
Molecular Weight: 86.13
MDL Number: MFCD00007014
MOL File: 590-86-3.mol
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
FLAVIS Number: 05.006 | 3-Methylbutanal
Flash point: 29 °F
Storage temp.: 2-8°C
Solubility: alcohol: miscible, soluble in Propylene glycol and oils.
Form: Liquid
Color: Clear colorless to light yellow
Specific Gravity: 0.80
Odor: at 0.10 % in dipropylene glycol. ethereal aldehydic chocolate peach fatty
Odor Type: aldehydic
Odor Threshold: 0.0001ppm
Biological source: synthetic
Explosive limit: 1.7-6.8%(V)
Water Solubility: 15 g/L (20 ºC)
JECFA Number: 258
Merck: 14,5229
BRN: 773692
Henry's Law Constant: 1.1×10-2 mol/(m3Pa) at 25℃
Stability: Stable, but light and air sensitive.
Incompatible with strong oxidizing agents, bases, reducing agents, air.
Cosmetics Ingredients Functions: PERFUMING, FRAGRANCE
InChI: 1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
InChIKey: YGHRJJRRZDOVPD-UHFFFAOYSA-N
SMILES: [H]C(=O)CC(C)C
LogP: 1.5 at 25℃ and pH7
CAS DataBase Reference: 590-86-3 (CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): 3-METHYLBUTYRALDEHYDE
FDA UNII: 69931RWI96
NIST Chemistry Reference: Butanal, 3-methyl-(590-86-3)
EPA Substance Registry System: Isovaleraldehyde (590-86-3)
UNSPSC Code: 85151701
NACRES: NA.24
Physical state: clear, liquid
Color: colorless
Odor: unpleasant
Melting point/freezing point: Freezing point: < -90 °C
Initial boiling point and boiling range: 90 °C - lit.
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: Upper explosion limit: 6,8 %(V) Lower explosion limit: 1,7 %(V)
Flash point: 0,5 °C - closed cup
Autoignition temperature: 210 °C at 1.020 hPa
Decomposition temperature: No data available
pH: No data available
Viscosity: Viscosity, kinematic: 0,69 mm2/s at 20 °C - OECD Test Guideline 114
Viscosity, dynamic: No data available
Water solubility: 15 g/l at 20 °C - OECD Test Guideline 105- soluble
Partition coefficient: n-octanol/water: log Pow: 1,5 at 25 °C - Bioaccumulation is not expected.
Vapor pressure: 40 hPa at 20 °C
Density: 0,803 g/cm3 at 25 °C - lit.
Relative density: No data available
Relative vapor density: No data available
Particle characteristics: No data available
Explosive properties: Not classified as explosive.
Oxidizing properties: none
Relative vapor: 2,97 - (Air = 1.0)
ECHA EINECS - REACH Pre-Reg: 209-691-5
FDA UNII: 69931RWI96
Nikkaji Web: J6.754G
Beilstein Number: 0773692
MDL: MFCD00007014
CoE Number: 94
XlogP3-AA: 1.00 (est)
Molecular Weight: 86.13390000
Formula: C5 H10 O
Appearance: colorless to pale yellow clear liquid (est)
Assay: 97.00 to 100.00
Food Chemicals Codex Listed: Yes
Specific Gravity: 0.79500 to 0.80200 @ 25.00 °C.
Pounds per Gallon - (est).: 6.615 to 6.673
Refractive Index: 1.38800 to 1.39100 @ 20.00 °C.
Melting Point: -51.00 °C. @ 760.00 mm Hg
Boiling Point: 90.00 to 93.00 °C. @ 760.00 mm Hg
Acid Value: 10.00 max. KOH/g
Vapor Pressure: 49.317001 mmHg @ 25.00 °C. (est)
Vapor Density: 2.9 (Air = 1)
Flash Point: 29.00 °F. TCC (-1.67 °C.)
logP (o/w): 1.267 (est)
Soluble in: alcohol
water, 14000 mg/L @ 20 °C (exp)
Insoluble in: water
Similar Items: note
valeraldehyde
2-oxovaleraldehyde
Chemical formula: C5H10O
Molar mass: 86.134 g·mol−1
Appearance: Colorless Liquid
Density: 0.785 g/mL at 20 °C
Melting point: −51 °C (−60 °F; 222 K)
Boiling point: 92 °C (198 °F; 365 K)
Solubility in water: Soluble in alcohol and ether, slightly soluble in water
Magnetic susceptibility (χ): −57.5×10−6 cm3/mol
Molecular Weight: 86.13 g/mol
XLogP3-AA: 1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 2
Exact Mass: 86.073164938 Da
Monoisotopic Mass: 86.073164938 Da
Topological Polar Surface Area: 17.1 Ų
Heavy Atom Count: 6
Formal Charge: 0
Complexity: 39.2
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Density: 0.785 g/mL
Molar volume: 109.7 mL/mol
Refractive index: 1.390
Molecular refractive power: 26.02 mL/mol
Melting point: -51 °C
Boiling point: 92 °C
Vapour pressure: 7 Torr
Critical pressure: 3.8 atm
Log10 partition octanol / water: 1.23
Molar mass: 86.13 g· mol −1
State of matter: fluid
Molecular Formula / Molecular Weight: C5H10O = 86.13
Physical State: Liquid
Storage Temperature: Refrigerated (0-10°C)
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive,Heat Sensitive
CAS RN: 590-86-3
Reaxys Registry Number: 773692
PubChem Substance ID: 87571573
SDBS (AIST Spectral DB): 350
Merck Index (14): 5229
MDL Number: MFCD00007014
Appearance: Colorless transparent liquid.
Odor: Strong malty, chocolate-like, fermented, fruity, nutty odor.
Physical State: Liquid at room temperature.
Molecular Formula: C₅H₁₀O.
Molecular Weight: 86.13 g/mol.
CAS Number: 590-86-3.
EC Number: 209-691-5.
Density: Approximately 0.80 g/cm³ at 20°C.
Melting Point: Approximately −51°C.
Boiling Point: Approximately 92–93°C.
Flash Point: Approximately 4°C (closed cup).
Autoignition Temperature: Approximately 196°C.
Vapor Pressure: Approximately 40–50 hPa at 20°C.
Relative Vapor Density: About 3 (air = 1).
Refractive Index: Approximately 1.388 at 20°C.
Evaporation Rate: Rapid due to high volatility.
Surface Tension: Relatively low, typical for small aldehydes.
Color Stability: May gradually yellow upon prolonged exposure to air and light.
Functional Group: Aldehyde.
Structure: Branched-chain aliphatic aldehyde.
Polarity: Moderately polar due to the carbonyl group.
Water Solubility: Slightly soluble in water.
Solubility: Miscible with ethanol, diethyl ether, acetone, benzene, chloroform, and many organic solvents.
XLogP: Approximately 1.2.
Hydrogen Bond Acceptor Count: 1.
Hydrogen Bond Donor Count: 0.
Rotatable Bond Count: 2.
Topological Polar Surface Area: Approximately 17 Ų.
Exact Mass: 86.073 Da.
Heavy Atom Count: 6.
Formal Charge: 0.
FIRST AID MEASURES of ISOVALERALDEHYDE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of ISOVALERALDEHYDE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of ISOVALERALDEHYDE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of ISOVALERALDEHYDE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of ISOVALERALDEHYDE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of ISOVALERALDEHYDE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
For more information, you can contact Ataman Kimya.
İstanbul Head Office: +90 216 577 10 10
Fax: +90 216 577 42 80
