4-methyl-2-oxovaleric acid, 816-66-0

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CODE104710 CODE104710
Product(s):
816-66-0 4-Methyl-2-oxovaleric Acid

Penta International Corporation

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For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
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Product(s):
13-61090 4-METHYL-2-OXOPENTANOIC ACID

TCI AMERICA

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CODE104710 CODE104710
Product(s):
K0025 4-Methyl-2-oxovaleric Acid >95.0%(GC)(T)
SDS

Name:	4-methyl-2-oxopentanoic acid
CAS Number:	816-66-0	3D/inchi
ECHA EINECS - REACH Pre-Reg:	212-435-5
FDA UNII:	4GUJ8AH400
Nikkaji Web:	J39.557I
Beilstein Number:	1701823
MDL:	MFCD00066204
CoE Number:	2263
XlogP3-AA:	0.90 (est)
Molecular Weight:	130.14330000
Formula:	C6 H10 O3
NMR Predictor:	Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments:
JECFA evaluated 4-Methyl-2-oxopentanoic acid and its sodium salt (CASrn 816-66-0 and 4502-00-5).

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
JECFA Food Flavoring:	633 4-methyl-2-oxopentanoic acid
DG SANTE Food Flavourings:	08.052 4-methyl-2-oxovaleric acid
FEMA Number:	3871 4-methyl-2-oxopentanoic acid
FDA:	No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):	816-66-0 ; 4-METHYL-2-OXOPENTANOIC ACID

Physical Properties:

Appearance:	pale yellow green clear liquid (est)
Assay:	98.00 to 100.00
Food Chemicals Codex Listed:	No
Specific Gravity:	1.05300 to 1.05800 @ 25.00 °C.
Pounds per Gallon - (est).:	8.762 to 8.804
Refractive Index:	1.43200 to 1.44200 @ 20.00 °C.
Melting Point:	8.00 to 10.00 °C. @ 760.00 mm Hg
Boiling Point:	251.00 °C. @ 760.00 mm Hg
Boiling Point:	82.00 to 83.00 °C. @ 11.00 mm Hg
Vapor Pressure:	0.239000 mmHg @ 25.00 °C. (est)
Flash Point:	182.00 °F. TCC ( 83.33 °C. )
logP (o/w):	0.133 (est)
Shelf Life:	12.00 month(s) or longer if stored properly.
Storage:	refrigerate in tightly sealed containers.
Soluble in:
	water, 1.676e+005 mg/L @ 25 °C (est)

Organoleptic Properties:

Odor Description:fruity

Odor and/or flavor descriptions from others (if found).

Cosmetic Information:

None found

Suppliers:

BOC Sciences

For experimental / research use only.

4-Methyl-2-oxovaleric Acid

Parchem

4-methyl-2-oxovaleric acid

Penta International

4-METHYL-2-OXOPENTANOIC ACID

Santa Cruz Biotechnology

For experimental / research use only.

4-Methyl-2-oxovaleric Acid ≥98%

Sigma-Aldrich: Aldrich

For experimental / research use only.

4-Methyl-2-oxovaleric acid purum, ≥98.0% (T)

sds

TCI AMERICA

For experimental / research use only.

4-Methyl-2-oxovaleric Acid >95.0%(GC)(T)

sds

Safety Information:

Preferred SDS: View
European information :
Most important hazard(s):
C - Corrosive.
R 34 - Causes burns. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. S 45 - In case of accident or if you feel unwell seek medical advice immediately.

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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
flavoring agents
Recommendation for 4-methyl-2-oxovaleric acid usage levels up to:
	not for fragrance use.

Maximised Survey-derived Daily Intakes (MSDI-EU):		ND (μg/capita/day)
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: 18
Click here to view publication 18
		average usual ppm	average maximum ppm
baked goods:		-	-
beverages(nonalcoholic):		0.05000	5.00000
beverages(alcoholic):		1.00000	5.00000
breakfast cereal:		-	-
cheese:		1.00000	10.00000
chewing gum:		0.50000	5.00000
condiments / relishes:		1.00000	5.00000
confectionery froastings:		1.00000	5.00000
egg products:		-	-
fats / oils:		0.50000	5.00000
fish products:		-	-
frozen dairy:		0.50000	10.00000
fruit ices:		1.00000	5.00000
gelatins / puddings:		0.50000	5.00000
granulated sugar:		-	-
gravies:		1.00000	5.00000
hard candy:		0.10000	5.00000
imitation dairy:		0.50000	5.00000
instant coffee / tea:		0.10000	1.00000
jams / jellies:		1.00000	5.00000
meat products:		-	-
milk products:		1.00000	10.00000
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		0.10000	1.00000
processed vegetables:		0.10000	1.00000
reconstituted vegetables:		-	-
seasonings / flavors:		50.00000	100.00000
snack foods:		-	-
soft candy:		0.30000	3.00000
soups:		1.00000	10.00000
sugar substitutes:		0.50000	5.00000
sweet sauces:		1.00000	10.00000

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):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: 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 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
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

Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): 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
View page or View pdf

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):816-66-0

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :70

National Institute of Allergy and Infectious Diseases:Data

WISER:UN 3265

WGK Germany:3

4-methyl-2-oxopentanoic acid

Chemidplus:0000816660

References:

	4-methyl-2-oxopentanoic acid
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	816-66-0
Pubchem (cid):	70
Pubchem (sid):	134977374

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
Golm Metabolome Database:	Search
Metabolomics Database:	Search
KEGG (GenomeNet):	C00233
HMDB (The Human Metabolome Database):	HMDB00695
FooDB:	FDB012607
YMDB (Yeast Metabolome Database):	YMDB00388
Export Tariff Code:	2918.30.9000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
FAO:	4-Methyl-2-oxopentanoic acid

Potential Blenders and core components note

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):note

	asparagus Search Trop Picture
	banana fruit Search Trop Picture
	cheese Search PMC Picture
	cocoa Search Trop Picture
	trigonella caerulea Search Trop Picture
	wine Search Picture

Synonyms:

a-ketoiso	caproic acid
alpha-ketoiso	caproic acid
2-keto-4-	methyl pentanoic acid
4-	methyl-2-oxo-pentanoic acid
4-	methyl-2-oxo-valeric acid
4-	methyl-2-oxopentanoic acid
4-	methyl-2-oxovalericacid
2-oxo-4-	methylpentanoic acid
2-keto-4-	methylvaleric acid
2-oxo-4-	methylvaleric acid
	pentanoic acid, 4-methyl-2-oxo-
iso	propylpyruvic acid

Articles:

PubMed:Structural Analysis Reveals the Substrate-Binding Mechanism for the Expanded Substrate Specificity of Mutant meso-Diaminopimelate Dehydrogenase.

PubMed:A novel test for IGT utilizing metabolite markers of glucose tolerance.

PubMed:[Determination of serum carbamazepine concentration and metabonomic analysis in rats].

PubMed:Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures.

PubMed:Determination of α-keto acids in pork meat and Iberian ham via tandem mass spectrometry.

PubMed:Identification of homophenylalanine biosynthetic genes from the cyanobacterium Nostoc punctiforme PCC73102 and application to its microbial production by Escherichia coli.

PubMed:Atomic-resolution structure of an N5 flavin adduct in D-arginine dehydrogenase.

PubMed:Xenorhabdus antibiotics: a comparative analysis and potential utility for controlling mastitis caused by bacteria.

PubMed:Isotopic determination of organic keto acid pentafluorobenzyl esters in biological fluids by negative chemical ionization gas chromatography/mass spectrometry.

PubMed:Quantitative analysis of intermediary metabolism in rat hepatocytes incubated in the presence and absence of ethanol with a substrate mixture including ketoleucine.

PubMed:Protein synthesis and degradation in the mammary gland of lactating goats.

PubMed:Determination of rates of protein synthesis, gain and degradation in intact hind-limb muscle of lambs.

PubMed:Amino acid uptake in the developing chick embryo heart. The effect of insulin on glycine and leucine accumulation.

PubMed:[Identification of 4-methyl-2-oxovaleric acid in the human blood].

Notes:

Found in bananas, asparagus, cheese, wine and cocoa. Constit. of Trigonella caerulea (sweet trefoil). Flavouring ingredient Ketoleucine is a metabolite that accumulates in Maple Syrup Urine Disease (MSUD) and shown to compromise brain energy metabolism by blocking the respiratory chain; this is of relevance to the understanding of the pathophysiology of the neurological dysfunction of MSUD patients. (PMID 14636955)

4-methyl-2-oxovaleric acid 4-methyl-2-oxopentanoic acid

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4-methyl-2-oxovaleric acid
4-methyl-2-oxopentanoic acid