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leucic acid
pentanoic acid, 2-hydroxy-4-methyl-

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Name:2-hydroxy-4-methylpentanoic acid
CAS Number: 498-36-2Picture of molecule3D/inchi
Other(deleted CASRN):10303-64-7
ECHA EINECS - REACH Pre-Reg:207-860-8
FDA UNII: 8RN4NSX3TY
Nikkaji Web:J6.108E
MDL:MFCD00004246
CoE Number:10118
XlogP3-AA:0.90 (est)
Molecular Weight:132.15924000
Formula:C6 H12 O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments:
Racemate.
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
DG SANTE Food Flavourings:08.090 2-hydroxy-4-methylvaleric acid
 
Physical Properties:
Appearance:colorless solid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 76.00 °C. @ 760.00 mm Hg
Boiling Point: 249.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.003000 mmHg @ 25.00 °C. (est)
Flash Point: 248.00 °F. TCC ( 120.00 °C. )
logP (o/w): 0.522 (est)
Soluble in:
 alcohol
 water, slightly
 water, 1.655e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
2-Hydroxy-4-methylvaleric Acid
Sigma-Aldrich: Aldrich
For experimental / research use only.
2-Hydroxyisocaproic acid 99%
TCI AMERICA
For experimental / research use only.
DL-Leucic Acid >98.0%(GC)(T)
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
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.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for leucic acid 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): 3800 (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): 10.0000050.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
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): --
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 15.0000075.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000
 
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

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 15 (FGE.15): Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 (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

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to 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 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009)
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

Scientific Opinion on Flavouring Group Evaluation 10, Revision 3 (FGE.10Rev3): 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):498-36-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :92779
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-hydroxy-4-methylpentanoic acid
Chemidplus:0000498362
 
References:
 2-hydroxy-4-methylpentanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):92779
Pubchem (sid):135052141
 
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
HMDB (The Human Metabolome Database):HMDB00665
FooDB:FDB022171
Export Tariff Code:2918.19.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
2-hydroxy-4-methyl pentanoic acid
2-hydroxy-4-methyl valeric acid
2-hydroxy-4-methyl-D-valeric acid
2-hydroxy-4-methylpentanoic acid
DL-2-hydroxy-4-methylpentanoic acid
2-hydroxy-4-methylvaleric acid
2-hydroxyhexanoic acid
2-hydroxyisocaproic acid
a-hydroxyisocaproic acid
alpha-hydroxyisocaproic acid
DL-2-hydroxyisocaproic acid
DL-a-hydroxyisocaproic acid
2-hydroxyisohexanoic acid
DL-leucate
dextro,laevo-leucic acid
DL-leucic acid
DL-leucicacid
 leucinic acid
4-methyl-2-hydroxypentanoic acid
 pentanoic acid, 2-hydroxy-4-methyl-
 pentanoic acid, 2-hydroxy-4-methyl-, (±)-
 

Articles:

PubMed:Investigation of the presence of β-hydroxy-β-methylbutyric acid and α-hydroxyisocaproic acid in bovine whole milk and fermented dairy products by a validated liquid chromatography-mass spectrometry method.
PubMed:Combining chemoinformatics with bioinformatics: in silico prediction of bacterial flavor-forming pathways by a chemical systems biology approach "reverse pathway engineering".
PubMed:2-hydroxyisocaproic acid is fungicidal for Candida and Aspergillus species.
PubMed:Chronic α-hydroxyisocaproic acid treatment improves muscle recovery after immobilization-induced atrophy.
PubMed:Synergistic effect of a novel cyclic pentadepsipeptide, neoN-methylsansalvamide, and paclitaxel on human multidrug resistance cancer cell lines.
PubMed:Biosynthesis of Athmu, a α,γ-hydroxy-β-amino acid of pahayokolides A-B.
PubMed:Structural analysis of a new cytotoxic demethylated analogue of neo-N-methylsansalvamide with a different peptide sequence produced by Fusarium solani isolated from potato.
PubMed:2-Hydroxyisocaproic acid (HICA): a new potential topical antibacterial agent.
PubMed:Regulatory phenotyping reveals important diversity within the species Lactococcus lactis.
PubMed:Pleofungins, novel inositol phosphorylceramide synthase inhibitors, from Phoma sp. SANK 13899. II. Structural elucidation.
PubMed:Biosynthetic characterization and chemoenzymatic assembly of the cryptophycins. Potent anticancer agents from cyanobionts.
PubMed:Intrahippocampal administration of the branched-chain alpha-hydroxy acids accumulating in maple syrup urine disease compromises rat performance in aversive and non-aversive behavioral tasks.
PubMed:Probing the role of a conserved M1 proline residue in 5-hydroxytryptamine(3) receptor gating.
PubMed:Enantioselective multidimensional gas chromatography-mass spectrometry in the analysis of urinary organic acids.
PubMed:Conformational study of two linear hexapeptides by two-dimensional NMR and computer-simulated modeling: implication for peptide cyclization in solution.
PubMed:Alpha-keto and alpha-hydroxy branched-chain acid interrelationships in normal humans.
PubMed:Alpha-keto acids are novel siderophores in the genera Proteus, Providencia, and Morganella and are produced by amino acid deaminases.
PubMed:In vivo characteristics of low molecular weight copolymers composed of L-lactic acid and various DL-hydroxy acids as biodegradable carriers for drug delivery systems.
PubMed:Bioactivation mechanism of L-thiomorpholine-3-carboxylic acid.
PubMed:[The growth of rats in renal compensatory adaptation in feeding with a supplemented diet of hydroxy-analogs of essential amino acids].
PubMed:Steric course of the rhodium-catalyzed decarbonylation of chiral 4-methyl-[1-3H,2-2H1]pentanal.
PubMed:Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin.
PubMed:Continuous enzymatically catalyzed production of L-leucine from the corresponding racemic hydroxy acid.
PubMed:Severe illness caused by the products of bacterial metabolism in a child with a short gut.
PubMed:Hydroxy acid metabolites of branched-chain amino acids in amniotic fluid.
PubMed:[1-Desaminopenicillamine, 8-alpha-hydroxyisocaproic acid] oxytocin. A selective inhibitor in rats of the uterine response to oxytocin.
PubMed:Biofunctional evaluation of two hydrogen bonds stabilizing the beta-turn in the acyclic component of oxytocin.
PubMed:Studies of urinary organic acid profiles of a patient with dihydrolipoyl dehydrogenase deficiency.
PubMed:Comparative utilization of the alpha-keto and D- and L-alpha-hydroxy analogs of leucine, isoleucine and valine by chicks and rats.
PubMed:Synthesis of [8-alpha-hydroxyisocaproic acid]oxytocin. Biological activities and comparison of its in vivo uterine actions to those of deamino-[8-alpha-hydroxyisocaproic acid]oxytocin, deamino-oxytocin and oxytocin.
PubMed:Biofunctional evaluation of a hydrogen bond linking the ring and tail beta-turns of oxytocin.
PubMed:Replacement of L-phenylalanine and L-leucine by alpha-hydroxy analogues in the diets of germfree rats.
 
Notes:
alpha-hydroxy analog of leucine. Leucinic acid has been isolated from amniotic fluid (PMID: 6467607), and have been found in a patient with dihydrolipoyl dehydrogenase deficiency (PMID 6688766). Leucinic acid is a bacterial metabolite present in the urine of patients with short bowel syndrome. (PMID 4018104) [HMDB]
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