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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:
773861
EC Number:
206-099-9
MDL number:
MFCD00004546
UNSPSC Code:
12352100
PubChem Substance ID:
24850187
NACRES:
NA.22

Quality Level

100

Assay

95%

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 (lit.)

storage temp.

2-8°C

SMILES string

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

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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

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °C - closed cup

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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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)
Tadahiro Shimazu et al.
Science (New York, N.Y.), 339(6116), 211-214 (2012-12-12)
Concentrations of acetyl-coenzyme A and nicotinamide adenine dinucleotide (NAD(+)) affect histone acetylation and thereby couple cellular metabolic status and transcriptional regulation. We report that the ketone body d-β-hydroxybutyrate (βOHB) is an endogenous and specific inhibitor of class I histone deacetylases
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
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
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
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