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55453

Sigma-Aldrich

β-Hydroxyisovaleric acid

≥95.0% (T)

Sinónimos:

3-Hydroxy-3-methylbutyric acid

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About This Item

Fórmula empírica (notación de Hill):
C5H10O3
Número de CAS:
625-08-1
Peso molecular:
118.13
Beilstein/REAXYS Number:
1743952
MDL number:
MFCD00059081
UNSPSC Code:
12352100
PubChem Substance ID:
57651529
NACRES:
NA.22

Quality Level

100

assay

≥95.0% (T)

refractive index

n20/D 1.4415 (lit.)

bp

88 °C/1 mmHg (lit.)

mp

−80 °C (lit.)

density

0.938 g/mL at 25 °C (lit.)

functional group

carboxylic acid

SMILES string

CC(C)(O)CC(O)=O

InChI

1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)

InChI key

AXFYFNCPONWUHW-UHFFFAOYSA-N

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Application

β-Hydroxyisovaleric acid can be used as as a precursor for steroid alcohols.
It is widely used in the synthesis of the anthrax tetrasaccharide and its analogs as anthrax vaccine candidates. β-hydroxyisovaleric acid can also be used in the synthesis of β-lactones by intramolecular dehydration condensation using 2-methyl-6-nitrobenzoic anhydride (MNBA).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Total synthesis of antigen Bacillus anthracis tetrasaccharide?creation of an anthrax vaccine candidate.
Werz, Daniel B and Seeberger, Peter H
Angewandte Chemie (International Edition in English), 44(39), 6315-6318 (2005)
De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide.
Guo, Haibing and O?Doherty, George A
The Journal of Organic Chemistry, 73(14), 5211-5220 (2008)
Carlos Hermano da Justa Pinheiro et al.
European journal of applied physiology, 112(7), 2531-2537 (2011-11-15)
Beta-hydroxy-beta-methylbutyrate (HMB) is a metabolite derived from leucine. The anti-catabolic effect of HMB is well documented but its effect upon skeletal muscle strength and fatigue is still uncertain. In the present study, male Wistar rats were supplemented with HMB (320
Shawn Portal et al.
European journal of applied physiology, 111(9), 2261-2269 (2011-02-18)
The use of ergogenic nutritional supplements is becoming inseparable from competitive sports. β-Hydroxy-β-Methylbutyric acid (HMB) has recently been suggested to promote fat-free mass (FFM) and strength gains during resistance training in adults. In this prospective randomized, double-blind, placebo-controlled study, we
C Flummer et al.
Journal of animal science, 90 Suppl 4, 372-374 (2013-02-13)
This trial was conducted to investigate whether β-hydroxy β-methyl butyrate (HMB) supplementation during late gestation and throughout lactation would influence colostrum and milk production of sows and neonatal piglet survival (0 to 24 h). Control sows (CON; n = 8)
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