Basic information
- CAS
13748-90-8- Standard SMILES
CC(C)C[C@H](O)C(=O)O- InChIKey
LVRFTAZAXQPQHI-YFKPBYRVSA-N- Molecular formula
- C6H12O3
- Average molar mass
- 132.16 g/mol
- Monoisotopic mass
- 132.07864424
Overview
(S)-2-hydroxy-4-methylpentanoic acid is the (S)-enantiomer of 2-hydroxy-4-methylpentanoic acid. Derived from the metabolism of the branched-chain amino acids, it belongs to the 2-hydroxycarboxylic acid group of amino acid metabolites. It is a (2S)-2-hydroxy monocarboxylic acid and a 2-hydroxy-4-methylvaleric acid. It is an enantiomer of a (R)-2-hydroxy-4-methylpentanoic acid.
Names & identifiers
- Preferred name
- Leucic acid, L-
- IUPAC
- (2S)-2-hydroxy-4-methylpentanoic acid
- English name
- L-Leucic acid
- Molecular formula
- C6H12O3
- Molecular weight
- 132.16
Names & synonyms
L-Leucic acidPentanoic acid, 2-hydroxy-4-methyl-, (2S)-Leucic acid, L-L-2-Hydroxy-4-methylvaleric acid6B33FPI2OZEINECS 237-329-6NSC-152493LEUCIC ACID, (S)-LEUCIC ACID, (+)-DTXSID80884643NSC 152493RefChem:798974
Show more names
2-HYDROXY-3-METHYLPENTANOIC ACIDLEUCIC ACIDHydroxyisocaproic acid2-HYDROXY-3-METHYLVALERIC ACID(s)-pentanoicaciL-a-Hydroxyisocaproic acid(S)-(-)-2-HYDROXYISOCAPROIC ACIDL-HICA
DTXCID60102407313748-90-8(S)-2-hydroxy-4-methylpentanoic acid(2S)-2-hydroxy-4-methylpentanoic acid(S)-leucic acidL-alpha-HYDROXYISOCAPROIC ACIDMFCD00064214L-2-hydroxyisocaproic acid
Database identifiers
- CAS
13748-90-8- PubChem CID
- 83697
- DTXSID
DTXSID80884643- ChEBI
CHEBI:44510- UNII
- 6B33FPI2OZ
- EC Number
- 237-329-6
- Nikkaji
- J84.592B
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 98.5
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]
LogP0.710
Melting Point78 - 80 °C
Physical DescriptionSolid
Collision Cross Section126.06 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 78 · 78-80 °C(lit.)
- Boiling point
- 277.83 °C · 277.83°C (rough estimate)
- Density
- 1.016 · 1.0160 (rough estimate)
- refractive index
- -26 ° · -26 ° (C=2, 1 %NaOH)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Aqueous Base (Slightly), DMSO (Sparingly), Water (Slightly)
- pka
- 3.86 · 3.86±0.21(Predicted)
- form
- Solid
- color
- White to Off-White
- optical activity
- 22 · [α]22/D 26.3°, c = 1 in 1 M NaOH
- Water Solubility
- almost transparency
- InChI
- InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m0/s1
- InChIKey
- LVRFTAZAXQPQHI-YFKPBYRVSA-N
- SMILES
- C(O)(=O)[C@@H](O)CC(C)C
- LogP
- 0.71 · 0.710
- CAS DataBase Reference
- 13748 · 13748-90-8(CAS DataBase Reference)
- FDA UNII
- 6 B33FPI2OZ · 6B33FPI2OZ
- EPA Substance Registry System
- 2 · Pentanoic acid, 2-hydroxy-4-methyl-, (2S)- (13748-90-8)
- UNSPSC Code
- 51113400 · 51113400
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HS Code
- 29181990 · 29181990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Warning
H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationPentanoic acid, 2-hydroxy-4-methyl-, (2S)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29181990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
General Manufacturing InformationPentanoic acid, 2-hydroxy-4-methyl-, (2S)-: INACTIVE
Applications
UsesL-Leucic Acid is a reagent in the synthesis of cryptophycins based macrocyclic depsipeptides which are used as tubulin inhibitors.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
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Additional notes
DefinitionChEBI: The (S)-enantiomer of 2-hydroxy-4-methylpentanoic acid. Derived from the metabolism of the branched-chain amino acids, it belongs to the 2-hydroxycarboxylic acid group of amino acid metabolites.
Related reactions
32 records
Compound notes
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