Isovaleraldehyd

3-Methylbutanal

HCID 11552CAS 26140-47-6

Grundinformationen

Standard-SMILES
CC(C)CC=O
InChIKey
YGHRJJRRZDOVPD-UHFFFAOYSA-N
Summenformel
C5H10O
Durchschnittliche Molmasse
86,13 g/mol
Monoisotopische Masse
86,07316494

Namen und Bezeichner

Bevorzugter Name
3-Methylbutanal
IUPAC
3-methylbutanal
Lokaler Name
Isovaleraldehyd
Englischer Name
Isovaleraldehyde
Summenformel
C5H10O
Molmasse
86.13

Namen und Synonyme

3-MethylbutanalISOVALERALDEHYDE590-86-33-MethylbutyraldehydeIsovaleralIsopentaldehydeButanal, 3-methyl-IsoamylaldehydeIsopentanalIsovalerylaldehydeIsovaleric aldehydebeta-Methylbutanal
Weitere Namen anzeigen
Butanal,3-methyl-3-Methyl-1-butanalFEMA 26923-Methylbutan-1-al3-Methybutanolbutanal,3-methyl
Isoamyl aldehyde1-Butanal, 3-methyl-Butyraldehyde, 3-methyl-FEMA No. 2692Aldehyde isovalerianiqueDTXSID102161969931RWI96NSC-404119

Datenbank-Bezeichner

CAS
26140-47-6、590-86-3
PubChem CID
11552
DTXSID
DTXSID1021619
ChEMBL
CHEMBL18360
ChEBI
CHEBI:16638
UNII
69931RWI96
EC Number
209-691-5
Nikkaji
J6.754G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
2
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

LogP1.31
Odor · 2 Einträge

Apple-like odor

POWERFUL PENETRATING, ACRID ODOR

TasteAT VERY LOW LEVELS THE FLAVOR IS WARM, HERBACEOUS, SLIGHTLY FRUIT, AND NUT-LIKE
Density · 4 Einträge

0.785 at 68 °F (USCG, 1999) - Less dense than water; will float

0.7977 g/cu cm at 20 °C

Relative density (water = 1): 0.8

0.795-0.815 (20 °C/20 °C)

Viscosity · 2 Einträge

0.58 mPa.S at 20 °C

0.725 mm²/s at 20 °C

Color/FormColorless liquid

Physikochemische Eigenschaften

Schmelzpunkt
-60 °C · -60 °C
Siedepunkt
90 °C · 90 °C (lit.)
Dichte
0.803 g/mL · 0.803 g/mL at 25 °C (lit.)
Dampfdichte
2.96 · 2.96 (vs air)
Dampfdruck
30 mm · 30 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.388(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1824) of reports.

Danger

H225 (> 99.9%): Highly Flammable liquid and vapor [Danger Flammable liquids];H317 (84.9%): May cause an allergic skin reaction [Warning Sensitization, Skin];H319 (> 99.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (85.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H411 (83.6%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P272, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P333+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1824 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 1824 reports by companies.;There are 24 notifications provided by 1823 of 1824 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Butanal, 3-methyl-

Regulation (EC) No 1831/2003 (amended)

Butanal, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanal, 3-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13620

3-Methylbutyraldehyde: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious); polymerization hazard]:;HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. (ERG, 2024)

Highly flammable. Vapour/air mixtures are explosive.

Health HazardsInhalation causes chest discomfort, nausea, vomiting, and headache. Contact of liquid with eyes or skin causes irritation. Ingestion causes irritation of mouth and stomach. (USCG, 1999)
Hazards Summary · 1 Eintrag

A mild skin irritant; [RTECS] Highly flammable and peroxidizable; A skin and eye irritant; [CAMEO] A severe eye irritant, based on animal studies; [CHEMINFO] Safe when used in food as a flavoring agent; [JECFA] An irritant; May cause liver impairment; [MSDSonline]

FDA Requirements · 1 Eintrag

Isovaleraldehyde 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.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents Not to Be Used: Water may be ineffective.;Fire Extinguishing Agents: Dry chemical, foam, carbon dioxide (USCG, 1999)

Use dry sand, carbon dioxide, dry powder. NO water. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Do NOT induce vomiting.

First Aid · 1 Eintrag

INHALATION: remove victim to fresh air; apply artificial respiration if required; get medical attention.;EYES: flush with water for at least 15 min.;SKIN: wipe off, wash well with soap and water.;INGESTION: induce vomiting; get medical attention. (USCG, 1999)

Safe StorageFireproof. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Fire Fighting Procedures · 1 Eintrag

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

Storage Conditions · 1 Eintrag

Materials which are toxic as stored or which can decompose into toxic components...should be stored in a cool, well ventilated place, out of the direct rays of the sun, away from areas of high fire hazard, and should be periodically inspected. Incompatible materials should be isolated...

Toxikologische Informationen

InteractionsIsovaleraldehyde markedly inhibited acetaldehyde oxidation in rat liver and was the most potent inhibitor of oxidation of various mitochondrial substrates.
Ecotoxicity Values · 5 Einträge

LC50; Species: Pimephales promelas (Fathead minnow, age 30 days, mean length 20.4 mm, mean weight 0.127 g); Conditions: flow through, 23.9 °C pH 7.58, hardness 49.3 mg/L CaCO3, alkalinity 47.8 mg/L CaCO3, dissolved oxygen 6.9 mg/L; Concentration: 3.25 mg/L for 96 hr (95% confidence limit: 2.98-3.54 mg/L) /97.3% purity/

EC50; Species: Pimephales promelas (Fathead minnow, age 30 days, mean length 20.4 mm, mean weight 0.127 g); Conditions: flow through, 23.9 °C pH 7.58, hardness 49.3 mg/L CaCO3, alkalinity 47.8 mg/L CaCO3, dissolved oxygen 6.9 mg/L; Concentration: 3.25 mg/L for 96 hr (95% confidence limit: 2.98-3.54 mg/L); Effect: Affected fish lost schooling behavior, swam near the surface, were hyperactive, had increased respiration and edema. Equilibrium loss was not observed prior to death. /97.3% purity/

LC50; Species Leuciscus idus (Ide); Conditions: static; Concentration 53 mg/L for 96 hr

LC50; Species Poecilia reticulata (Guppy); Conditions: semi-static; Concentration 13.3 mg/L for 14 days

For more Ecotoxicity Values (Complete) data for 3-METHYLBUTANAL (11 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 23(SRC), determined from a water solubility of 1.4X10+4 mg/L(2) and a regression-derived equation(3), indicates that 3-methylbutanal is expected to have very high mobility in soil(SRC). Volatilization of 3-methylbutanal from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.0X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 50 mm Hg(4), and its water solubility(2). 3-Methylbutanal is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). A theoretical oxygen demand of 16.1% after 24 hrs in a waste treatment plant(5) suggests that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 23(SRC), determined from a water solubility of 1.4X10+4 mg/L(2) and a regression-derived equation(3), indicates that 3-methylbutanal is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.0X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 50 mm Hg(4), and water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hours and 4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 3-Methylbutanal is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). A theoretical oxygen demand of 16.1% after 24 hrs in a waste treatment plant(6) suggests that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-methylbutanal, which has a vapor pressure of 50 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-methylbutanal is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 14 hours(SRC), calculated from rate constants of 2.78X10-11(3) and 2.74X10-11(4) cu cm/molecule-sec at 25 °C. Vapor-phase 3-methylbutanal is also degraded in the atmosphere by reaction with photochemically-produced nitrate radicals; the half-life for this reaction in air is estimated to be 44 hours(SRC), calculated from rate constant of 1.82X10-14 cu cm/sec(3). Aliphatic aldehydes absorb available solar radiation and dissociate to produce free radical fragments(5); therefore 3-methylbutanal may be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1 Eintrag

3-Methylbutanal has been detected in coffee aroma(1), in the extract of edible Korean Chamchwi(2), in blue cheese aroma(3), as a flavor constituent in gari(4), as a volatile component of Beaufort cheese(5), in cured pork(6), in bacon pork, smoke, and flavor(7) in roasted filberts(8), in chick pea(9), in volatiles from pork, mutton, chicken and beef(10) in beef sukiyaki from the beef and soy sauce(11), in Italian-type dry-cured ham(12), and in fried chicken(13). 3-Methylbutanal has also been detected as a flavor volatile from cooked sweet corn at the following concns: canned cream corn (10 ppb), canned kernel (19 ppb), frozen kernel (7 ppb), and fresh kernel (<4 ppb)(14). 3-Methylbutanal has been found as a volatile component of scrambled eggs using eggs from the supermarket packed in polystyrene (122 ng/g), fresh eggs, not stored (126 ng/g), and fresh eggs stored in polystyrene for two weeks (16 ng/g)(15). 3-Methylbutanal was also found as a volatile component of polystyrene egg cartons(15). 3-Methylbutanal was found in popcorn using wet extraction method at 1200 ug/kg and dry extraction method at 430 ug/kg(16). Commercial rice cakes were found to contain 440-620 ppb of 3-methylbutanal(17). 3-Methylbutanal was measured at 9720 ng/g, 77,100 ng/g, 22,100 ng/g and 12,400 ng/g in anchovy paste, big eyed herring paste, hair tail viscera paste, and shrimp paste, respectively(18). 3-Methylbutanal was detected in whole and ground musty sorghum with direct helium-purge method and with supercritical fluid extraction method(19).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Milk ConcentrationsENVIRONMENTAL: 3-Methylbutanal was detected, not quantified, in cold storage, store bought milk in Australia(1).

Regulatorische Informationen

Regulatory Information · 6 Einträge

Chemical: Butanal, 3-methyl-

Regulation (EC) No 1831/2003 (amended)

Butanal, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanal, 3-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13620

3-Methylbutyraldehyde: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

FDA Requirements · 1 Eintrag

Isovaleraldehyde 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.

TSCA Requirements · 2 Einträge

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Butanal, 3-methyl- is included on this list. Effective date 9/30/91; Sunset date: 6/30/98.

Sicherheitsdaten

F
13
wgk
1
tsca
TSCA listed
ridadr
UN 1989 3/PG 2
hs_code
29121900
RTECS-Nr.
ES3450000

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

...inhibits oxidation of other mitochondrial substrates, including acetaldehyde

...Isovaleraldehyde is also a degradation product of leucine that is associated with hepatic encephalopathy.

Metabolism/Metabolites · 4 Einträge

Aldehydes are readily oxidized to organic acids, which, in turn, can serve as substrates for fatty acid oxidation pathways and the Krebs cycle. ... Oxidation of aldehydes is catalyzed by aldehyde dehydrogenase, which has been found in the brain, erythrocytes, liver, kidney, heart, and placenta. /Aldehydes/

... The detoxification of aldehydes can be seen to proceed basically via two routes: (1) an oxidation to yield readily metabolized acids; (2) inactivation by reaction with sulfhydryl groups, particularly glutathione. Under conditions that either deplete glutathione levels, or that result in an inhibition of aldehyde dehydrogenase (for example, Antabuse treatment), the acute and chronic effects of aldehyde toxicity might be more fully expressed. /Aldehydes/

3-Methylbutanal is a volatile aldehyde which in the rat is derived, at least in part, from colonic bacterial breakdown of leucine. It has been proposed as a toxin in the pathogenesis of hepatic encephalopathy in man. The mean plasma 3-methylbutanal concentration in non-fasting patients with hepatic encephalopathy, 0.244 umol/liter (range 0-1.30) was not significantly different from the mean value in controls, 0.116 umol/liter (0-0.349). Oral leucine feeding resulted in significant increases in plasma 3-methylbutanal concentrations in both control subjects and patients with cirrhosis. Peak leucine and 3-methylbutanal values occurred at approximately the same time and usually within 120 min of leucine ingestion. Pre-treatment with neomycin had no effect on the results of leucine feeding. No changes occurred in the clinical condition or psychometric performance of patients with cirrhosis fed leucine despite increases in plasma 3-methylbutanal of up to 700% over basal values. In man plasma 3-methylbutanal, at least in part, derives from ingested leucine independently of the action of colonic bacteria.

The cytochrome P450-catalyzed formation of olefinic products from a series of xenobiotic aldehydes has been demonstrated. Isobutyraldehyde and trimethylacetaldehyde, but not propionaldehyde, are converted to the predicted olefinic products, suggesting a requirement for branching at the alpha carbon. In addition, the four C5 aldehydes of similar hydrophobicity were compared for their ability to undergo the reaction. The straight-chain valeraldehyde gave no olefinic products with five different rabbit liver microsomal P450 isozymes. However, increasing activity was seen with the other isomers in the order of isovaleraldehyde, 2-methylbutyraldehyde, and trimethylacetaldehyde, with all of the P450 cytochromes.

Verwendung und Herstellung

Uses · 4 Einträge

Found in orange, lemon, peppermint, and other oils; [Merck Index] Used flavors, fragrances, and to make isovaleric acid, pharmaceuticals, and resins; [HSDB] Used to make pesticides, solvents, and softeners; [eChemPortal: SIDSUNEP]

Reported uses (PPM): (FEMA, 2005);Table: Reported uses (PPM): (FEMA, 2005) [Table#1746]

FLAVOR INGREDIENT; FRAGRANCE INGREDIENT IN PERFUMES; CHEM INT FOR ISOVALERIC ACID

Flavoring, perfumes, pharmaceuticals, synthetic resins.

U.S. Production · 2 Einträge

2023: 75,000 - <500,000 lb;2022: 1,000,000 - <8,500,000 lb;2021: 75,000 - <500,000 lb;2020: 75,000 - <500,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1745]

Consumer UsesFragrance
Industry UsesIntermediate
Methods of Manufacturing · 3 Einträge

REACTION OF BUTENES WITH CARBON MONOXIDE AND HYDROGEN IN THE PRESENCE OF A COBALT CATALYST (OXO PROCESS), FOLLOWED BY SEPARATION OF ISOMERS; OXIDATION OF ISOAMYL ALCOHOL WITH SODIUM DICHROMATE AND SULFURIC ACID

Made by oxidation of isoamyl alcohol with Na2Cr2O7 and H2SO4.

3-Methylbutanal ... is prepared by hydroformylation of isobutene.

Household ProductsInformation on 1 consumer products that contain Isopentanal in the following categories is provided:;• Auto Products
Anwendungen · 2 Einträge

OccurrenceReported 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.

VerwendenIsovaleraldehyde 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.

Darstellung

synthetischeBy oxidation of isoamyl alcohol.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.

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