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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
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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.)

functional group

carboxylic acid
hydroxyl

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;[1] enantioselective reactions at the 2-, 3- and 4-positions via the cyclic acetal with aldehydes;[2] preparation of (R)-β-butyrolactone.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2964
BCCJ6334
BCCF3498
BCCC5741
BCBX5509

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A. Griesbech et al.
Helvetica Chimica Acta, 70, 1320-1320 (1987)
D. Seebach et al.
Modern Synthetic Methods, 4, 125-125 (1986)
Journal of the American Chemical Society, 110, 4763-4763 (1988)
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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Questions

1–2 of 2 Questions  

  1. お世話なっております。基本的な質問ですみません。LC-MSMS分析の標品、定量目的として使用したいと考えております。注文済みではありますがまだ納品はされておりまｓん。到着後保存は冷蔵庫でする予定ですが、秤量するなどのときに長時間室温に置いて置いたりすると、３HBが重合してしまうことはありますか？(２量体や３量体などになってしまうことはありますか？）

    1 answer

    1. While the recommended storage temperature for this product is 2-8C, it is not shipped refrigerated. The refrigerated storage recommendation is to preserve long-term shelf life, but the product should be okay at room temperature for short periods of time, such as during weighing. For long-term storage, the product needs to be refrigerated in order for the quality to be guaranteed.

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  2. この＃54920は細胞培養に使用可能でしょうか？エンドトキシンのチェックなどはされているでしょうか？

    1 answer

    1. This product has not been tested for the suitability oincell culture. The (R)-3-Hydroxybutyric acid is more often used in the preparation of copolymers or in the preparation of (3R,4R)-4-acetoxy-3-[(R)-1-(formyloxy)ethyl]-2-azetidinone. This product would have to be validated for use in any in vitro applications such as cell culture. Our product H6501, DL-B-Hydroxybutyric acid sodium salt, while also not tested for use in culture, is more frequently used for in vitro studies. Please see the product detail page for product H6501: https://www.sigmaaldrich.com/product/sigma/h6501.

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