55452
D-α-Hydroxyisovaleric acid
≥98.0% (T)
Synonym(s):
(R)-2-Hydroxy-3-methylbutyric acid
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About This Item
Empirical Formula (Hill Notation):
C5H10O3
CAS Number:
Molecular Weight:
118.13
UNSPSC Code:
51113400
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1721139
Assay:
≥98.0% (T)
Form:
solid
InChI key
NGEWQZIDQIYUNV-SCSAIBSYSA-N
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
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
Quality Level
Related Categories
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.
signalword
Warning
hcodes
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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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)
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
H.-O. Kim et al.
The Journal of Organic Chemistry, 52, 4531-4531 (1987)
W. Hartwig et al.
Liebigs Ann. Chem., 1952-1952 (1982)
A Haese et al.
Journal of molecular biology, 243(1), 116-122 (1994-10-14)
Enniatin synthetase catalyzes the biosynthesis of N-methylated cyclohexadepsipeptides. The 347 kDa enzyme is encoded by the esyn1 gene of Fusarium scirpi and contains two domains (EA and EB) homologous to each other and to regions of other microbial peptide synthetases.
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