leucic acid
pentanoic acid, 2-hydroxy-4-methyl-
Identification
| Name | leucic acid |
| IUPAC | 2-hydroxy-4-methylpentanoic acid |
| CAS Number | 498-36-2 |
| EINECS | 207-860-8 |
| FDA UNII | 8RN4NSX3TY |
| Molecular Formula | C6 H12 O3 |
| Molecular Weight | 132.15924000 |
| MDL Number | MFCD00004246 |
| Nikkaji Number | J6.108E |
| CoE Number | 10118 |
Regulatory
| 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 |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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 |
| Dairy products, excluding products of category 02.0 (01.0) | 3.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 2.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 3.00000 |
| Processed fruit (04.1) | 2.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 5.00000 |
| Bakery wares (07.0) | 10.00000 |
| Meat and meat products, including poultry and game (08.0) | 2.00000 |
| 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) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 10.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 5.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 10.00000 |
| Ready-to-eat savouries (15.0) | 15.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 5.00000 |
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Potential Uses
Natural Occurrence
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-, (±)-
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.