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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
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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.[1]
  • 3-hydroxy-N-(4-methoxyphenyl)-(3S)-butanamide by treating with 4-methoxyaniline in the presence of acid-amine coupling reagent.[2]

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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E Fernqvist-Forbes et al.
Diabetes care, 14(11), 1006-1012 (1991-11-01)
To study the effects of mental stress on the absorption kinetics of insulin and on glucose homeostasis and lipolysis in insulin-dependent diabetes mellitus (IDDM). Nine IDDM patients were exposed to the Stroop color word conflict test (CWT) during 40 min
Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides
Sandrock DL, et al.
Journal of the American Chemical Society, 132(48), 17108-17110 (2010)
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
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
Vickie E Baracos et al.
The Journal of nutrition, 136(1 Suppl), 237S-242S (2005-12-21)
Many of the features of BCAA metabolism in the tumor-bearing state are similar to the other disease states that feature involuntary weight loss and skeletal muscle atrophy. These states are generally characterized by altered BCAA availability (low BCAA intakes, elevated
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