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444286

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

444286-VAR:
444286-BULK:
444286-1G:

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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Concise total synthesis of botryolide B
Mohapatra DK, et al.
Royal Society of Chemistry Advances, 4(16), 8335-8340 (2014)
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)
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.
Natalia N Dioubankova et al.
Organic letters, 4(26), 4607-4610 (2002-12-20)
[reaction: see text] Two series of seco-pseudonucleoside synthons were synthesized from (R)-(+)-alpha-hydroxy-gamma-butyrolactone and (R)-(-)-pantolactone by aminolysis, side-chain protection, dimethoxytritylation, and phosphitylation or solid-phase attachment. The phosphoramidites and solid supports were used in automated DNA synthesis to prepare oligonucleotides modified with
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