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isovaleraldehyde

Chemical Structure

General Material Information

Preferred name isovaleraldehyde
Trivial Name 3-Methylbutanal
Short Description 3-methylbutyraldehyde
Formula C5 H10 O
CAS Number 590-86-3
FEMA Number 2692
Flavis Number 5.006
ECHA Number 209-691-5
FDA UNII 69931RWI96
Nikkaji Number J6.754G
Beilstein Number 0773692
MDL MFCD00007014
COE Number 94
xLogP3-AA 1.00 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 258 3-methylbutyraldehyde
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 590-86-3 ; 3-METHYLBUTYRALDEHYDE
Synonyms
  • 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
  • Butyraldehyde, 3-methyl-
  • 3-Methylbutanal
  • Isopentanal
  • Isovaleral
  • Isovaleric aldehyde
  • β-Methylbutanal
  • 3-Methylbutyraldehyde
  • Isoamylaldehyde
  • iso-Valeraldehyde
  • 3-Methyl-1-butanal
  • NSC 404119

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

3-methylbutanal
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:590-86-3
Pubchem (cid):11552
Pubchem (sid):134977076
Flavornet:590-86-3
Pherobase:View
Publications by Info
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
Publications by Google Patents
Dimethyl sulfide, beta-damascenone, 3-methylbutanal, and 3-methylbutyric acid
Publications by US Patents
3,992,457 - Flavoring and perfuming ingredients
Publications by PubMed
An Exploration on the Suitability of Airborne Carbonyl Compounds Analysis in relation to Differences in Instrumentation (GC-MS versus HPLC-UV) and Standard Phases (Gas versus Liquid).
Recent advances in thermal desorption-gas chromatography-mass spectrometery method to eliminate the matrix effect between air and water samples: Application to the accurate determination of Henry's law constant.
Isovaleraldehyde elimination by UV/TiO2 photocatalysis: comparative study of the process at different reactors configurations and scales.
Alcohol dehydrogenases from Scheffersomyces stipitis involved in the detoxification of aldehyde inhibitors derived from lignocellulosic biomass conversion.
Major odorants released as urinary volatiles by urinary incontinent patients.
Experimental approach to assess sorptive loss properties of volatile organic compounds in the sampling bag system.
Novel approach to test the relative recovery of liquid-phase standard in sorbent-tube analysis of gaseous volatile organic compounds.
Release of offensive odorants from the combustion of barbecue charcoals.
Analysis of two commercially available bortezomib products: differences in assay of active agent and impurity profile.
A combined application of thermal desorber and gas chromatography to the analysis of gaseous carbonyls with the aid of two internal standards.
Sorptive removal of odorous carbonyl gases by water.
Total synthesis of (-)-muraymycin D2 and its epimer.
Influences of sampling volume and sample concentration on the analysis of atmospheric carbonyls by 2,4-dinitrophenylhydrazine cartridge.
Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification.
Enzyme inactivation and quality preservation of sake by high-pressure carbonation at a moderate temperature.
Behavioural responses of Tribolium castaneum (Herbst) to volatiles identified from dry cocoa beans.
Ethanol analysis from biological samples by dual rail robotic autosampler.
A transcriptome analysis of isoamyl alcohol-induced filamentation in yeast reveals a novel role for Gre2p as isovaleraldehyde reductase.
Two highly divergent alcohol dehydrogenases of melon exhibit fruit ripening-specific expression and distinct biochemical characteristics.
Critical aspects of the determination of pentafluorobenzyl derivatives of aldehydes by gas chromatography with electron-capture or mass spectrometric detection: Validation of an optimized strategy for the determination of oxygen-related odor-active aldehydes in wine.
Molecular breeding of the Mureka-non-forming sake koji mold from Aspergillus oryzae by the disruption of the mreA gene.
Molecular cloning of the isoamyl alcohol oxidase-encoding gene (mreA) from Aspergillus oryzae.
Structural characterization of new malvidin 3-glucoside-catechin aryl/alkyl-linked pigments.
Tungsten-containing aldehyde oxidoreductase of Eubacterium acidaminophilum.
Glu 103 Gln site-directed mutation causes an alteration in physical properties of spinach betaine aldehyde dehydrogenase.
Determination of carbonyl compounds in air by electrochromatography.
Airborne aldehydes from heating rosin core solder and liquid rosin flux to soldering temperatures.
Effect of methanol-containing additive on the emission of carbonyl compounds from a heavy-duty diesel engine.
The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests.
Biotransformation in organic media by enzymes and whole cells.
Detection of toluene in an adipoceratous body.
Catalysis by cytochrome P-450 of an oxidative reaction in xenobiotic aldehyde metabolism: deformylation with olefin formation.
Manganese(II) catalyzes the bicarbonate-dependent oxidation of amino acids by hydrogen peroxide and the amino acid-facilitated dismutation of hydrogen peroxide.
A study of chemoreception based on membrane fluidity and circular dichroism of a membrane assembly model--role of protein penetrating into the lipid bilayer.
Thermal desorption-gas chromatography of plasma isovaleraldehyde in hepatic encephalopathy in man.
[Gas chromatographic determination of isovaleraldehyde in the air of a work area].
Binding of isovaleraldehyde, an attractant, to zoospores of the fungus Phytophthora palmivora in relation to zoospore chemotaxis.
Purification and properties of aldehyde dehydrogenase from Proteus vulgaris.
Poisoning by 2-methylbutyraldehyde (isovaleraldehyde).

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C07329
HMDB (The Human Metabolome Database):HMDB06478
FooDB:FDB003954
YMDB (Yeast Metabolome Database):YMDB00499
Export Tariff Code:2912.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 86.133903503418
Specific gravity @ 25 °C
Pounds per Gallon 6.615 to 6.673
Refractive Index 1.388 to 1.391 @ 20 °C
Boiling Point 90 to 93°C @ 760 mm Hg
Acid Value 10 max KOH/g
Vapor Pressure 49.317001 mmHg @ 25 °C
Vapor Density 2.9
Flash Point TCC Value -1.67 °C TCC
logP (o/w) 1.267 est
Solubility
alcohol Yes
water, 14000 mg/L @ 20 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Aldehydic
ethereal, aldehydic, chocolate, peach, fatty
Odor strength high , recommend smelling in a 0.10 % solution or less
Substantivity 96 hour(s) at 100.00 %
Luebke, William tgsc, (2017) At 0.10 % in dipropylene glycol. ethereal aldehydic chocolate peach fatty
Flavor Type: Fruity
fruity, dry, green, chocolate, nutty, leafy, cocoa
Luebke, William tgsc, (2017) Fruity dry green chocolate nutty leafy cocoa
Used in coffee, nut and cocoa flavors. Cocoa
General comment FRUITY,DRY,GREEN,CHOCOLATE,NUT

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 12 - Extremely flammable.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 07 - Keep container tightly closed.
S 16 - Keep away from sources of ignition - No Smoking.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Human Experience:
1 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 5600 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(12), Pg. 53, 1987.

intraperitoneal-rat LD50 800 mg/kg
Clinical Science. Vol. 61, Pg. 451, 1981.

oral-mouse LD50 4750 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 27(5), Pg. 60, 1983.

oral-guinea pig LD50 2950 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 27(5), Pg. 60, 1983.

Dermal Toxicity:
skin-rabbit LD50 3180 ul/kg
LIVER: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
National Technical Information Service. Vol. OTS0535072

subcutaneous-mouse LD50 2000 mg/kg
Annales Pharmaceutiques Francaises. Vol. 14, Pg. 710, 1956.

skin-guinea pig LD50 > 8000 mg/kg
Food and Chemical Toxicology. Vol. 26, Pg. 379, 1988.

Inhalation Toxicity:
inhalation-mouse LC50 50770 mg/m3
BEHAVIORAL: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 27(5), Pg. 60, 1983.

inhalation-rat LC50 42700 mg/m3/4
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
National Technical Information Service. Vol. OTS0535072

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for isovaleraldehyde usage levels up to:
0.1000 % in the fragrance concentrate.
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3. Update in publication number(s): 29
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 21.0000029.00000
beverages(nonalcoholic): 2.000004.00000
beverages(alcoholic): 0.4000010.00000
breakfast cereal: --
cheese: --
chewing gum: 760.000005000.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 8.0000012.00000
fruit ices: --
gelatins / puddings: 8.0000011.00000
granulated sugar: --
gravies: --
hard candy: 3.000003.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 0.100000.50000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 12.0000017.00000
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 3, Revision 1 (FGE.03Rev1): Acetals of branched- and straight-chain aliphatic saturated primary alcohols and branched- and straight-chain saturated or unsaturated aldehydes, an ester of a hemiacetal and an orthoester of formic acid, from chemical groups 1, 2 & 4 Commission Regulation (EC) No 1565/2000 of 18 July 2000) [1] - Scientific Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)on a request from the Commission
View page or View pdf

Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):590-86-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11552
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1989
WGK Germany:1
3-methylbutanal
Chemidplus:0000590863
EPA/NOAA CAMEO:hazardous materials
RTECS:ES3450000 for cas# 590-86-3