isohexanal
pentanal, 4-methyl-
 
Notes:
produced from side-chain cleavage of 20,22-dihydroxycholesterol. 4-Methylpentanal is an intermediate in the metabolism of C21-Steroid hormone. It is a substrate for Cytochrome P450 11A1 (mitochondrial). [HMDB]
  • BOC Sciences
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      Product(s):
      1119-16-0 4-Methylvaleraldehyde
       
  • CSA
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CAS Number: 1119-16-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 214-273-0
FDA UNII: T0AO9E93RH
Nikkaji Web: J49.658H
Beilstein Number: 0506059
MDL: MFCD00871507
CoE Number: 10369
XlogP3-AA: 1.30 (est)
Molecular Weight: 100.16084000
Formula: C6 H12 O
NMR Predictor: Predict (works with chrome or firefox)
Category: flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
DG SANTE Food Flavourings: 05.166  4-methylpentanal
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Physical Properties:
Appearance: colorless clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.79900 to 0.80500 @  25.00 °C.
Pounds per Gallon - (est).: 6.648 to  6.698
Refractive Index: 1.39900 to 1.41500 @  20.00 °C.
Boiling Point: 117.00 to  118.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 16.915001 mmHg @ 25.00 °C. (est)
Flash Point: 64.00 °F. TCC ( 17.78 °C. )
logP (o/w): 1.777 (est)
Soluble in:
 alcohol
 water, 3930 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
4-Methylvaleraldehyde
Santa Cruz Biotechnology
For experimental / research use only.
4-Methylpentanal
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the CSA
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Safety Information:
Preferred SDS: View
 
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.
Oral/Parenteral Toxicity:
oral-rat LD50  5660 ul/kg
(Smyth et al., 1962)

oral-rat LD50  5660 uL/kg
American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.

Dermal Toxicity:
skin-rabbit LD50 4460 ul/kg
American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.

skin-rabbit LD50 4460 uL/kg
American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.

Inhalation Toxicity:
inhalation-rat LCLo 16000 ppm/4H
American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.

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Safety in Use Information:
Category: flavoring agents
Recommendation for isohexanal usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.0012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 1000 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 2.0000010.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 4.0000020.00000
Chewing gum (05.0): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 2.0000010.00000
Bakery wares (07.0): 5.0000025.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 2.0000010.00000
Foodstuffs intended for particular nutritional uses (13.0): 3.0000015.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): --
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 4.0000020.00000
Ready-to-eat savouries (15.0): 5.0000025.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 2.0000010.00000
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Safety References:
European Food Safety Athority(EFSA): Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Flavouring Group Evaluation 1, Revision 1 (FGE.01Rev 1): Branched-chain aliphatic saturated aldehydes, carboxylic acids and related esters of primary alcohols and branched-chain carboxylic acids from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Scientific Opinion of the 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 01 Rev2 (FGE.01 Rev2): Branched-chain aliphatic saturated aldehydes, carboxylic acids and related esters of primary alcohols and branched-chain carboxylic acids from chemical groups 1 and 2
View page or View pdf
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 1119-16-0
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 129
National Institute of Allergy and Infectious Diseases: Data
 4-methylpentanal
Chemidplus: 0001119160
RTECS: YV4200000 for cas# 1119-16-0
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References:
 4-methylpentanal
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 129
Pubchem (sid): 134979777
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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
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C02373
HMDB (The Human Metabolome Database): HMDB01318
FooDB: FDB022551
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cheese
Search  PMC Picture
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Synonyms:
isocaproaldehyde
4-methyl pentanal
4-methyl valeraldehyde
4-methylpentaldehyde
4-methylpentanal
4-methylvaleraldehyde
 pentanal, 4-methyl-
 valeraldehyde, 4-methyl-
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Articles:
PubMed: Rat aldose reductase-like protein (AKR1B14) efficiently reduces the lipid peroxidation product 4-oxo-2-nonenal.
PubMed: Crystallization and preliminary X-ray analysis of a rat aldose reductase-like protein (AKR1B14).
PubMed: AKR1B7 (mouse vas deferens protein) is dispensable for mouse development and reproductive success.
PubMed: Activation of the glucocorticoid receptor or liver X receptors interferes with growth hormone-induced akr1b7 gene expression in rat hepatocytes.
PubMed: Decreased expression of cyclic adenosine monophosphate-regulated aldose reductase (AKR1B1) is associated with malignancy in human sporadic adrenocortical tumors.
PubMed: Adrenocorticotropin/3',5'-cyclic AMP-mediated transcription of the scavenger akr1-b7 gene in adrenocortical cells is dependent on three functionally distinct steroidogenic factor-1-responsive elements.
PubMed: Hormonal and developmental regulation of the mouse aldose reductase-like gene akr1b7 expression in Leydig cells.
PubMed: Steroidogenic factor-1 controls the aldose reductase akr1b7 gene promoter in transgenic mice through an atypical binding site.
PubMed: Role of three SF-1 binding sites in the expression of the mvdp/akr1-b7 isocaproaldehyde reductase in Y1 cells.
PubMed: Physiological functions and hormonal regulation of mouse vas deferens protein (AKR1B7) in steroidogenic tissues.
PubMed: Adrenal tumorigenesis targeted by the corticotropin-regulated promoter of the aldo-keto reductase AKR1B7 gene in transgenic mice.
PubMed: SF-1 (steroidogenic factor-1), C/EBPbeta (CCAAT/enhancer binding protein), and ubiquitous transcription factors NF1 (nuclear factor 1) and Sp1 (selective promoter factor 1) are required for regulation of the mouse aldose reductase-like gene (AKR1B7) expression in adrenocortical cells.
PubMed: Product of side-chain cleavage of cholesterol, isocaproaldehyde, is an endogenous specific substrate of mouse vas deferens protein, an aldose reductase-like protein in adrenocortical cells.
PubMed: Aldose reductase is a major reductase for isocaproaldehyde, a product of side-chain cleavage of cholesterol, in human and animal adrenal glands.
PubMed: Steric course of the rhodium-catalyzed decarbonylation of chiral 4-methyl-[1-3H,2-2H1]pentanal.
PubMed: New assays for the enzymatic conversion of cholesterol to pregnenolone.
PubMed: The final step of side-chain cleavage of cholesterol by adrenocortical cytochrome P-450(scc) studied with [22(-18)O]20,22-dihydroxycholesterols, [18O]isocaproaldehyde, [18O]water and atmospheric [18O]oxygen.
PubMed: Implication of ligand modified spectra of cytochrome P-450 associated with pregnenolone synthesis in mitochondria from corpus luteum.
PubMed: Formation of isocaproaldehyde in the enzymatic cleavage of cholesterol side chain by adrenal extract.
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