| Identification | More | [Name]
L-LEUCIC ACID | [CAS]
13748-90-8 | [Synonyms]
2-HYDROXY-3-METHYLPENTANOIC ACID
2-HYDROXY-3-METHYLVALERIC ACID
L-ALPHA-HYDROXYISOCAPROIC ACID
LEUCIC ACID
L-LEUCIC ACID
(S)-2-HYDROXY-4-METHYLVALERIC ACID
(S)-(-)-2-HYDROXYISOCAPROIC ACID
(s)-pentanoicaci
L-2-hydroxy-4-methylvaleric acid
(S)-(-)-2 HYDROXYSOCAPROIC ACID,98%
Pentanoic acid, 2-hydroxy-4-methyl-, (2S)-
(2S)-2-hydroxy-4-methylpentanoic acid
Hydroxyisocaproic acid
L-LEUCIC ACID ( AKA ) 2-HYDROXY ISOCAPROIC ACID
S-2-Hydroxy-4-methylpentanoic acid
(S)-Leucic acid
2-Hydroxy-4-methylvaleric acid, L-2-Hydroxy-4-methylpentanoic acid, L-Leucic acid
(2S)-2-Hydroxy-4-methylvaleric acid
(S)-4-Methyl-2-hydroxyvaleric acid | [EINECS(EC#)]
237-329-6 | [Molecular Formula]
C6H12O3 | [MDL Number]
MFCD00064214 | [Molecular Weight]
132.16 | [MOL File]
13748-90-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
78-80 °C(lit.) | [Boiling point ]
277.83°C (rough estimate) | [density ]
1.0160 (rough estimate) | [refractive index ]
-26 ° (C=2, 1 %NaOH) | [storage temp. ]
-15°C
| [solubility ]
Aqueous Base (Slightly), DMSO (Sparingly), Water (Slightly) | [form ]
Solid | [pka]
3.86±0.21(Predicted) | [color ]
White to Off-White | [Optical Rotation]
[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]
0.710 | [CAS DataBase Reference]
13748-90-8(CAS DataBase Reference) | [EPA Substance Registry System]
Pentanoic acid, 2-hydroxy-4-methyl-, (2S)- (13748-90-8) |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
L-Leucic Acid is a reagent in the synthesis of cryptophycins based macrocyclic depsipeptides which are used as tubulin inhibitors. | [Definition]
ChEBI: 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. | [Synthesis]
GENERAL STEPS: L-leucine (24.92 g, 0.189 mol) was dissolved in 1.25 M H2SO4 (125 mL), stirred and cooled to 0°C. An aqueous solution of sodium nitrite (19.73 g, 0.286 mol) (100 mL) was added dropwise with stirring. After addition, the reaction mixture was continued to be stirred at 0°C for 2 hours, and then brought to room temperature and stirred for 15 hours. After completion of the reaction, the reaction mixture was extracted with ether (6 x 75 mL). The organic layers were combined, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure to remove the ether to give the crude product L-α-hydroxyisocaproic acid (2c or 2d). The crude product was purified by solvent recrystallization from hexane-ether mixture. | [IC 50]
Microbial Metabolite; Human Endogenous Metabolite | [References]
[1] Organic Letters, 2012, vol. 14, # 16, p. 4246 - 4249
[2] Organic Letters, 2006, vol. 8, # 14, p. 2993 - 2996
[3] European Journal of Organic Chemistry, 2009, # 31, p. 5390 - 5405
[4] ACS Chemical Neuroscience, 2013, vol. 4, # 8, p. 1204 - 1216
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 1, p. 11 - 14 |
|
|