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54917

Sigma-Aldrich

(R)-2-Hydroxybutyric acid

≥97.0% (T)

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About This Item

Empirical Formula (Hill Notation):
C4H8O3
CAS Number:
20016-85-7
Molecular Weight:
104.10
Beilstein:
1720939
MDL number:
MFCD01318570
UNSPSC Code:
51113400
PubChem Substance ID:
57651488
NACRES:
NA.22

Assay

≥97.0% (T)

form

solid

optical purity

enantiomeric ratio: ≥99:1 (GC)

mp

50-54 °C

functional group

carboxylic acid
hydroxyl

storage temp.

2-8°C

SMILES string

CC[C@@H](O)C(O)=O

InChI

1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1

InChI key

AFENDNXGAFYKQO-GSVOUGTGSA-N

Other Notes

Chiral building block

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315 - H318 - H335

Hazard Classifications

Eye Dam. 1 - 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
BGBC5339V
BGBC5338V
BGBC0276V
BCBM4388V
BCBH4738V

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M N Romanelli et al.
Chirality, 8(8), 579-584 (1996-01-01)
The enantiomers of 3-alpha-tropyl 2-(phenylthio)butyrate (SM32, 1) were prepared by chiral synthesis and tested for analgesic, cognition-enhancing, and ACh-releasing properties. They show enantioselectivity in some of the tests, the eutomer being related in configuration to R-(+)-hyoscyamine.
K.J. Hale et al.
Tetrahedron Letters, 36, 6965-6965 (1995)
M N Romanelli et al.
Chirality, 8(3), 225-233 (1996-01-01)
The enantiomers of two alpha-tropanyl esters, SM21 (1) and PG9 (2), derived from (+)-R-hyoscyamine, that act by increasing the central cholinergic tone, were obtained by esterification after resolution of the corresponding racemic acids [(-)-S-1, (-)-R-2 and (+)-S-2] and by stereospecific
Ferhan Siddiqi et al.
Biochemistry, 44(25), 9013-9021 (2005-06-22)
Mandelate racemase (MR, EC 5.1.2.2) from Pseudomonas putida catalyzes the Mg(2+)-dependent 1,1-proton transfer that interconverts the enantiomers of mandelate. Crystal structures of MR reveal that the phenyl group of all ground-state ligands is located within a hydrophobic cavity, remote from
R Guerranti et al.
Biochimica et biophysica acta, 1568(1), 45-52 (2001-12-04)
Rat liver L-threonine dehydrogenase is a mitochondrial enzyme which transforms L-threonine either into aminoacetone or into acetyl-CoA. We show that it is inhibited by several fatty acids and their derivatives: short chain fatty acids, L-2-hydroxybutyrate and D-3-hydroxybutyrate, long chain fatty
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