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Merck
CN

379093

(S)-(+)-2-Hydroxy-3-methylbutyric acid

99%, optical purity ee: 99% (GLC)

Synonym(s):

L-α-Hydroxyisovaleric acid

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About This Item

Linear Formula:
(CH3)2CHCH(OH)CO2H
CAS Number:
17407-55-5
Molecular Weight:
118.13
UNSPSC Code:
51113400
NACRES:
NA.22
PubChem Substance ID:
24863611
MDL number:
MFCD00066443
Beilstein/REAXYS Number:
1721140

Key Documents

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Product Name

(S)-(+)-2-Hydroxy-3-methylbutyric acid, 99%, optical purity ee: 99% (GLC)

InChI

1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m0/s1

SMILES string

CC(C)[C@H](O)C(O)=O

InChI key

NGEWQZIDQIYUNV-BYPYZUCNSA-N

assay

99%

form

solid

optical activity

[α]20/D +19°, c = 1 in chloroform

optical purity

ee: 99% (GLC)

bp

124-125 °C/13 mmHg (lit.)

mp

68-70 °C (lit.)

functional group

carboxylic acid
hydroxyl

Quality Level

200

Related Categories

Application

A useful chiral building block for peptide synthesis. Used in the preparation of the cytotoxic didemnin cyclopeptides and of the antineoplastic agent dolastatin 15.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBX7430V
24196LJV
MKBB0904
24196LJ
02928JJ

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Journal of the American Chemical Society, 112, 7659-7659 (1990)
Schmidt, U. et al.
Synthesis, 294-294 (1991)
Pettit, G.R. et al.
Journal of the American Chemical Society, 113, 6692-6692 (1991)
O Arad et al.
Biopolymers, 29(12-13), 1633-1649 (1990-10-01)
Depsipeptide analogues of peptide sequences can help in elucidating the role of specific hydrogen bonds in determining the conformation in peptides. The repeating pentapeptide and hexapeptide sequences of elastin have been suggested to contain a type II beta-turn with a
L Hagenfeldt et al.
Clinica chimica acta; international journal of clinical chemistry, 169(1), 77-83 (1987-10-30)
N-Lactylvaline, N-lactylleucine, N-lactylisoleucine and the N-2-hydroxyisovaleryl conjugates of glycine, valine, leucine and isoleucine have been identified in urine from a patient with the intermediate type of maple syrup urine disease.
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