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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.)

functional group

carboxylic acid

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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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
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
Elahe Masaeli et al.
PloS one, 8(2), e57157-e57157 (2013-03-08)
Tissue engineering techniques using a combination of polymeric scaffolds and cells represent a promising approach for nerve regeneration. We fabricated electrospun scaffolds by blending of Poly (3-hydroxybutyrate) (PHB) and Poly (3-hydroxy butyrate-co-3- hydroxyvalerate) (PHBV) in different compositions in order to
Yasmin Schuermann et al.
Scientific reports, 8(1), 16170-16170 (2018-11-06)
Ovulation is triggered by gonadotropin surge-induced signaling cascades. To study the role of extracellular signal-regulated kinase 1/2 (ERK1/2) in bovine ovulation, we administered the pharmacological inhibitor, PD0325901, into the preovulatory dominant follicle by intrafollicular injection. Four of five cows treated
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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