Isovaleraldehyde
Synonym(s):3-Methylbutanal;3-Methylbutyraldehyde;NSC 404119
- CAS NO.:590-86-3
- Empirical Formula: C5H10O
- Molecular Weight: 86.13
- MDL number: MFCD00007014
- EINECS: 209-691-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-25 16:21:11
What is Isovaleraldehyde?
Description
Isovaleraldehyde, formally 3-methylbutanal, is a pungent liquid that occurs in natural oils such as orange, lemon, peppermint, and eucalyptus. It is also found in processed foods such as beer, cheese, and chocolate. Its odor has been described variously from “apple-like” to “suffocating”.
In addition to its natural sources, isovaleraldehyde can be synthesized in several ways, including
Isovaleraldehyde’s strong aroma makes it useful (in small amounts) as a perfume component. So . . . perfume, chocolate, and beer . . . what else could you possibly need for Valentine’s Day?
Chemical properties
3-Methylbutyraldehyde has a choking, powerful, acrid, pungent, apple-like odor. This compound is also reported to have a fruity, fatty, animal, almond odor.
Chemical properties
Isovaleraldehyde is a colorless, low-solubility liquid with a pungent odor similar to that of apples.
Occurrence
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.
The 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.
The Uses of Isovaleraldehyde
In artificial flavors and perfumes.
The Uses of Isovaleraldehyde
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.
Definition
ChEBI: 3-methylbutanal is a methylbutanal that is butanal substituted by a methyl group at position 3. It 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.
Preparation
By oxidation of isoamyl alcohol.
General Description
Colorless liquid with a weak suffocating odor. Floats on water. Produces an irritating vapor. It is a metabolite found in or produced by Saccharomyces cerevisiae.
Air & Water Reactions
Highly flammable.
Reactivity Profile
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.
Health Hazard
Inhalation causes chest discomfort, nausea, vomiting, and headache. Contact of liquid with eyes or skin causes irritation. Ingestion causes irritation of mouth and stomach.
Properties of Isovaleraldehyde
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 | n |
FEMA | 2692 | 3-METHYLBUTYRALDEHYDE |
Flash point: | 29 °F |
storage temp. | 2-8°C |
solubility | alcohol: miscible |
form | Liquid |
appearance | colorless liquid |
color | Clear colorless to light yellow |
Specific Gravity | 0.80 |
Odor | at 0.10 % in dipropylene glycol. ethereal aldehydic chocolate peach fatty |
Odor Threshold | 0.0001ppm |
explosive limit | 1.7-6.8%(V) |
Water Solubility | 15 g/L (20 ºC) |
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, air. |
CAS DataBase Reference | 590-86-3(CAS DataBase Reference) |
NIST Chemistry Reference | Butanal, 3-methyl-(590-86-3) |
EPA Substance Registry System | Isovaleraldehyde (590-86-3) |
Safety information for Isovaleraldehyde
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Exclamation Mark Irritant GHS07 Environment GHS09 |
GHS Hazard Statements |
H225:Flammable liquids H317:Sensitisation, Skin H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H411:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Isovaleraldehyde
InChIKey | YGHRJJRRZDOVPD-UHFFFAOYSA-N |
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Bondbay Pharmaceuticals Pvt Ltd
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