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54925

Sigma-Aldrich

(S)-3-Hydroxybutyric acid

≥97.0%

Synonym(s):

(+)-3-Hydroxy-n-butyric acid, (3S)-3-Hydroxybutanoic acid, (S)-β-Hydroxybutanoic acid, (S)-(+)-β-Hydroxybutyric acid, L-β-Hydroxybutyric acid

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About This Item

Empirical Formula (Hill Notation):
C4H8O3
CAS Number:
6168-83-8
Molecular Weight:
104.10
Beilstein:
1720567
EC Number:
228-209-4
MDL number:
MFCD00137685
UNSPSC Code:
51113400
PubChem Substance ID:
57651490
NACRES:
NA.22

Quality Level

100

Assay

≥97.0%

form

powder or crystals

optical activity

[α]20/D +25±1°, c = 6% in H2O

mp

45-50 °C

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-/m0/s1

InChI key

WHBMMWSBFZVSSR-VKHMYHEASA-N

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Application

(S)-3-Hydroxybutyric acid can be used as a reagent in the synthesis of:
  • S-(2-acetamidoethyl) (S)-3-hydroxybutanethioate by reacting with acetylcysteamine in the presence of coupling reagent.
  • 3-hydroxy-N-(4-methoxyphenyl)-(3S)-butanamide by treating with 4-methoxyaniline in the presence of acid-amine coupling reagent.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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
BCCH5053
BCBZ6962
BCBM0192V
1381970V
1381970

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H A Byrne et al.
Diabetes care, 23(4), 500-503 (2000-06-17)
To evaluate the performance of a hand-held ketone sensor that is able to measure blood beta-hydroxybutyrate (beta-HBA) concentrations within 30 s in patients with diabetic ketoacidosis (DKA) and patients who attend a weight management clinic. Two groups of patients were
Tsung-Yi Lin et al.
ACS synthetic biology, 2(11), 635-642 (2013-05-10)
Fluvirucin B1 , produced by Actinomadura vulgaris, is a 14-membered macrolactam active against a variety of infectious fungi as well as influenza A. Despite considerable interest from the synthetic community, very little information is available regarding the biosynthetic origins of
Aron Altorjay et al.
World journal of gastroenterology, 11(11), 1623-1628 (2005-03-24)
With the availability of a minimally invasive approach, anti-reflux surgery has recently experienced a renaissance as a cost-effective alternative to life-long medical treatment in patients with gastroesophageal reflux disease (GERD). We are not aware of the fact whether reflux episodes
Lisa A Paige et al.
International journal of geriatric psychiatry, 22(5), 418-423 (2006-10-19)
Metabolomics, the global science of biochemistry, is an emerging field that enables detection and quantification of small molecules involved in metabolic and signaling pathways. Metabolic signatures for disease and its treatment could provide valuable biomarkers and insights about disease mechanisms.
U M Nadgir et al.
Endocrine research, 27(1-2), 41-46 (2001-06-29)
We quantitated serial serum beta-hydroxybutyrate (beta-OHB) levels using the Ketosite method in 9 children with IDDM who were treated for diabetic ketoacidosis (DKA) and compared them to urinary ketone measurements by dipstick. Persistent elevations of serum beta-OHB were seen in
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