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Merck

55452

Sigma-Aldrich

D-α-Hydroxyisovaleric acid

≥98.0% (T)

Sinónimos:

(R)-2-Hydroxy-3-methylbutyric acid

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About This Item

Fórmula empírica (notación de Hill):
C5H10O3
Número de CAS:
Peso molecular:
118.13
Beilstein/REAXYS Number:
1721139
MDL number:
UNSPSC Code:
51113400
PubChem Substance ID:
NACRES:
NA.22

assay

≥98.0% (T)

form

solid

optical activity

[α]20/D −17±1°, c = 1% in chloroform

mp

64-67 °C

functional group

carboxylic acid
hydroxyl

SMILES string

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

InChI

1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m1/s1

InChI key

NGEWQZIDQIYUNV-SCSAIBSYSA-N

Application

D-α-Hydroxyisovaleric acid may be used in the preparation of biodegradable, optically active and isotactic poly(D-2-hydroxy-3-methylbutanoic acid).

Other Notes

This chiral α-hydroxy acid is used for the synthesis of peptides and depsipeptides. It is further used as chiral building block. Synthesis of α-substituted α-hydroxy acids via dioxolanone intermediates.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Visite la Librería de documentos

H.-O. Kim et al.
The Journal of Organic Chemistry, 52, 4531-4531 (1987)
R L Johnson
Journal of medicinal chemistry, 23(6), 666-669 (1980-06-01)
The following N-(alpha-hydroxylakanoyl) derivatives of Leu-Val-Phe-OCH3 were synthesized and tested for their ability to inhibit human amniotic renin: D- and L-alpha-hydroxyisocaproyl-Leu-Val-Phe-OCH3, D- and L-alpha-hydroxyisovaleryl-Leu-Val-Phe-OCH3, L-2-hydroxy-3-phenylpropanoyl-Leu-Val-Phe-OCH3, and D- and L-alpha-hydroxyphenylacetyl-Leu-Val-Phe-OCH3. Analysis of the compounds through the use of Dixion plots showed
Hetero-stereocomplex formation between substituted poly (lactic acid) s with linear and branched side chains, poly (l-2-hydroxybutanoic acid) and poly (d-2-hydroxy-3-methylbutanoic acid).
Tsuji H and Hayakawa T.
Polymer, 55(3), 721-726 (2014)
W. Hartwig et al.
Liebigs Ann. Chem., 1952-1952 (1982)
Identification of 3-hydroxyisovalerylcarnitine in the urine of a patient with multiple carboxylase deficiency.
T Nakanishi et al.
Annals of clinical biochemistry, 30 ( Pt 3), 318-320 (1993-05-01)

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