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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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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
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
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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)
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