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Sigma-Aldrich

(R)-(+)-α-Hydroxy-γ-butyrolactone

95%, optical purity ee: 98% (GLC)

Synonym(s):

(R)-4,5-Dihydro-3-hydroxy-2(3H)-furanone

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About This Item

Empirical Formula (Hill Notation):
C4H6O3
CAS Number:
56881-90-4
Molecular Weight:
102.09
Beilstein:
80588
MDL number:
MFCD00211246
UNSPSC Code:
12352005
PubChem Substance ID:
24868111
NACRES:
NA.22

Assay

95%

form

liquid

optical activity

[α]23/D +66°, c = 1.15 in chloroform

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.467 (lit.)

bp

133 °C/10 mmHg (lit.)

density

1.309 g/mL at 25 °C (lit.)

SMILES string

O[C@@H]1CCOC1=O

InChI

1S/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2/t3-/m1/s1

InChI key

FWIBCWKHNZBDLS-GSVOUGTGSA-N

Application

(R)-(+)-α-Hydroxy-γ-butyrolactone can be used as a starting material to synthesize:
  • δ-Azaproline by reacting with benzyloxycarbonyl aminophthalimide via Mitsunobu reactions.
  • Homochiral (R)-2,4-dihydroxybutyramide seco-pseudonucleoside reagents.
  • Botryolide B via esterification and ring-closing metathesis reaction.
  • Pregnane derivatives containing γ-butyrolactones as potential glucocorticoid agonists.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Novel glucocorticoid antedrugs possessing a 21-(?-lactone) ring.
Angell RM, et al.
Journal of the Chemical Society. Perkin Transactions 1, 6, 831-839 (2002)
Novel glucocorticoid antedrugs possessing a 21-(γ-lactone) ring
Angell RM, et al.
Journal of the Chemical Society. Perkin Transactions 1, 4(6), 831-839 (2002)
Concise total synthesis of botryolide B
Mohapatra DK, et al.
Royal Society of Chemistry Advances, 4(16), 8335-8340 (2014)
Xiaohui Gou et al.
Frontiers in physiology, 11, 686-686 (2020-07-17)
Dentin sialoprotein (DSP), the NH2-terminal fragment of dentin sialophosphoprotein (DSPP), is essential for dentin formation and further processed into small fragments inside the odontoblasts. Gelatinases, including matrix metalloproteinases 9 (MMP9) and MMP2, were able to cleave DSP(P) in tooth structures.
Efficient synthesis of enantiomerically pure (S)-d-azaproline starting from (R)-a-hydroxy-?-butyrolactone via the Mitsunobu reaction.
Voss E, et al.
Tetrahedron Asymmetry, 20(15), 1809-1812 (2009)
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