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54920

Sigma-Aldrich

(R)-3-Hydroxybutyric acid

≥98.0% (T)

Synonym(s):

(3R)-3-Hydroxybutanoic acid, (3R)-Hydroxybutyrate, 3R-Hydroxybutanoic acid, D-β-Hydroxybutyrate

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About This Item

Empirical Formula (Hill Notation):
C4H8O3
CAS Number:
625-72-9
Molecular Weight:
104.10
Beilstein/REAXYS Number:
1720568
EC Number:
210-909-6
MDL number:
MFCD00066257
UNSPSC Code:
51113400
PubChem Substance ID:
57651489
NACRES:
NA.22

Quality Level

100

assay

≥98.0% (T)

form

solid

optical activity

[α]20/D −25±1°, c = 6% in H2O

mp

49-50 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@@H](O)CC(O)=O

InChI

1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1

InChI key

WHBMMWSBFZVSSR-GSVOUGTGSA-N

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Application

(R)-3-Hydroxybutyric acid may be used in the preparation of copolymers by reacting with various hydroxyalkanoic acids.1 It may also be used in the preparation of (3R,4R)-4-acetoxy-3-[(R)-1-(formyloxy)ethyl]-2-azetidinone.2

Other Notes

Important chiral starting material; enantioselective reactions at the 2-, 3- and 4-positions via the cyclic acetal with aldehydes; preparation of (R)-β-butyrolactone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Journal of the American Chemical Society, 110, 4763-4763 (1988)
D. Seebach et al.
Modern Synthetic Methods, 4, 125-125 (1986)
A. Griesbech et al.
Helvetica Chimica Acta, 70, 1320-1320 (1987)
J L Hansen et al.
Clinical chemistry, 24(3), 475-479 (1978-03-01)
Methods are described for direct assays of lactate, pyruvate, beta-hydroxybutyrate, and acetoacetate in plasma with the GEMSAEC centrifugal analyzer. The methods for lactate, beta-hydroxybutyrate, and acetoacetate are kinetic and ratiometric, eliminating the need for specimen-blank assays. The pyruvate method is
Jin Hee Kim et al.
Diabetes, obesity & metabolism (2018-11-09)
To investigate sodium-glucose cotransporter 2 inhibitor (SGLT2i)-induced changes in ketogenic enzymes and transporters in normal and diabetic mice models. Normal mice were randomly assigned to receive either vehicle or SGLT2i (25 mg/kg/d by oral gavage) for 7 days. Diabetic mice were treated
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