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166898

Sigma-Aldrich

3-Hydroxybutyric acid

95%

Synonym(s):

(±)-3-Hydroxybutanoic acid, DL-β-Hydroxybutyric acid

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About This Item

Linear Formula:
CH3CH(OH)CH2COOH
Molecular Weight:
104.10
Beilstein/REAXYS Number:
773861
EC Number:
206-099-9
MDL number:
MFCD00004546
UNSPSC Code:
12352100
PubChem Substance ID:
24850187
NACRES:
NA.22

Quality Level

100

assay

95%

form

liquid

refractive index

n20/D 1.443 (lit.)

bp

118-120 °C/2 mmHg (lit.)

solubility

ethanol: soluble 50 mg/mL, clear

density

1.126  g/mL at 25 °C
1.126 g/mL at 25 °C (lit.)

functional group

carboxylic acid
hydroxyl

storage temp.

2-8°C

SMILES string

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

InChI

1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)

InChI key

WHBMMWSBFZVSSR-UHFFFAOYSA-N
WHBMMWSBFZVSSR-UHFFFAOYSA-N

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General description

3-Hydroxybutyric acid forms films of random copolymer with (R)-3-hydroxypentanoic acid, (R)-3-hydroxyhexanoic acid, 4-hydroxybutyric acid, 6-hydroxyhexanoic acid and (S,S)-lactide by the melt-crystallized method. It is an important intermediate for the fine chemical industry.

Application

3-Hydroxybutyric acid was used in enantioselective synthesis of D-(-)-3-hydroxybutyric acid by Escherichia coli.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS4453
MKCR6412
MKCP6201
MKCP0675
MKCN1979

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Silvia Brojanigo et al.
Polymers, 12(7) (2020-07-09)
Due to oil shortage and environmental problems, synthetic plastics have to be replaced by different biodegradable materials. A promising alternative could be polyhydroxyalkanoates (PHAs), and the low-cost abundant agricultural starchy by-products could be usefully converted into PHAs by properly selected
A A A Jacobs et al.
Animal : an international journal of animal bioscience, 7(9), 1508-1516 (2013-04-20)
Stearoyl-CoA desaturase (SCD) in the bovine mammary gland introduces a cis-double bond at the Δ9 position in a wide range of fatty acids (FA). Several long-chain polyunsaturated fatty acids (PUFA) inhibit expression of SCD, but information on the effect of
M Derno et al.
Journal of dairy science, 96(2), 971-980 (2012-12-12)
In addition to plasma metabolites and hormones participating as humoral signals in the control of feed intake, oxidative metabolic processes in peripheral organs also generate signals to terminate feeding. Although the degree of oxidation over longer periods is relatively constant
Misha Zilberter et al.
Journal of neurochemistry, 125(1), 157-171 (2012-12-18)
Deficient energy metabolism and network hyperactivity are the early symptoms of Alzheimer's disease (AD). In this study, we show that administration of exogenous oxidative energy substrates (OES) corrects neuronal energy supply deficiency that reduces the amyloid-beta-induced abnormal neuronal activity in
Hai Jun Gao et al.
FEMS microbiology letters, 213(1), 59-65 (2002-07-20)
Wild-type bacteria including Escherichia coli normally do not produce extracellular D-(-)-3-hydroxybutyric acid (3HB). To produce extracellular chiral 3HB, a new pathway for synthesis of 3HB was constructed by simultaneous expression of genes of beta-ketothiolase (phbA), acetoacetyl-CoA reductase (phbB), phosphor-transbutyrylase (ptb)
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