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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:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Journal of the American Chemical Society, 110, 4763-4763 (1988)
D. Seebach et al.
Modern Synthetic Methods, 4, 125-125 (1986)
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
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
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