L-LEUCIC ACID Chemical Properties

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. 

Sealed in dry,Room Temperature

solubility 

Aqueous Base (Slightly), DMSO (Sparingly), Water (Slightly)

pka

3.86±0.21(Predicted)

form 

Solid

color 

White to Off-White

optical activity

[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)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29181990

MSDS

• Language:English Provider:SigmaAldrich

L-LEUCIC ACID Usage And Synthesis

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

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