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55452

Sigma-Aldrich

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:
17407-56-6
Molecular Weight:
118.13
Beilstein:
1721139
MDL number:
MFCD00066442
UNSPSC Code:
51113400
PubChem Substance ID:
57651528
NACRES:
NA.22

Assay

≥98.0% (T)

form

solid

optical activity

[α]20/D −17±1°, c = 1% in chloroform

mp

64-67 °C

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
W. Hartwig et al.
Liebigs Ann. Chem., 1952-1952 (1982)
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)
H.-O. Kim et al.
The Journal of Organic Chemistry, 52, 4531-4531 (1987)
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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