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Merck

55453

β-Hydroxyisovaleric acid

≥95.0% (T)

β-Hydroxyisovaleric acid

Synonym(s):

3-Hydroxy-3-methylbutyric acid

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About This Item

Empirical Formula (Hill Notation):
C5H10O3
CAS Number:
625-08-1
Molecular Weight:
118.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57651529
MDL number:
MFCD00059081
Beilstein/REAXYS Number:
1743952

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Product Name

β-Hydroxyisovaleric acid, ≥95.0% (T)

InChI

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

SMILES string

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

InChI key

AXFYFNCPONWUHW-UHFFFAOYSA-N

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
hydroxyl

Quality Level

100

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Show Differences

1 of 4

This Item
554524515057400
β-Hydroxyisovaleric acid ≥95.0% (T)

Sigma-Aldrich

55453

β-Hydroxyisovaleric acid

D-α-Hydroxyisovaleric acid ≥98.0% (T)

Sigma-Aldrich

55452

D-α-Hydroxyisovaleric acid

Pamoic acid ≥97.0% (T)

Sigma-Aldrich

45150

Pamoic acid

Indole-3-propionic acid ≥99.0% (T)

Sigma-Aldrich

57400

Indole-3-propionic acid

assay

≥95.0% (T)

assay

≥98.0% (T)

assay

≥97.0% (T)

assay

≥99.0% (T)

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

200

density

0.938 g/mL at 25 °C (lit.)

density

-

density

-

density

-

mp

−80 °C (lit.)

mp

64-67 °C

mp

≥300 °C (dec.)

mp

~133 °C

refractive index

n20/D 1.4415 (lit.)

refractive index

-

refractive index

-

refractive index

-

bp

88 °C/1 mmHg (lit.)

bp

-

bp

-

bp

-

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.[1][2] β-hydroxyisovaleric acid can also be used in the synthesis of β-lactones by intramolecular dehydration condensation using 2-methyl-6-nitrobenzoic anhydride (MNBA).[3]

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

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4719
BCCL4915
BCCJ1521
BCCD7728
BCBZ3601

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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)
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)
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
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