Skip to Content
MilliporeSigma

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

Slide 1 of 1
Sign Into View Organizational & Contract Pricing

Select a Size

1 G
$108.00

$108.00

List Price$144.00Save 25%
Web-Only Promotion

Available to ship TODAYDetails

Request a Bulk Order
Ships Every 4 weeks

About This Item

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

Key Documents

View All Documentation

Skip To

Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

100

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.)

functional group

ester
hydroxyl

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

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
42279727748755201
(R)-(+)-α-Hydroxy-γ-butyrolactone 95%, optical purity ee: 98% (GLC)

Sigma-Aldrich

444286

(R)-(+)-α-Hydroxy-γ-butyrolactone

(S)-β-Hydroxy-γ-butyrolactone 96%

Sigma-Aldrich

422797

(S)-β-Hydroxy-γ-butyrolactone

2-Methyltetrahydro-3-furanone 98%

Sigma-Aldrich

277487

2-Methyltetrahydro-3-furanone

DL-α-Hydroxy-β,β-dimethyl-γ-butyrolactone purum, ≥97.0% (T)

Sigma-Aldrich

55201

DL-α-Hydroxy-β,β-dimethyl-γ-butyrolactone

assay

95%

assay

96%

assay

98%

assay

≥97.0% (T)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

form

liquid

form

-

form

liquid

form

solid

bp

133 °C/10 mmHg (lit.)

bp

98-100 °C/0.3 mmHg (lit.)

bp

139 °C (lit.)

bp

-

density

1.309 g/mL at 25 °C (lit.)

density

1.241 g/mL at 25 °C (lit.)

density

1.034 g/mL at 25 °C (lit.)

density

-

refractive index

n20/D 1.467 (lit.)

refractive index

n20/D 1.464 (lit.)

refractive index

n20/D 1.429 (lit.)

refractive index

-

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.[1]
  • Homochiral (R)-2,4-dihydroxybutyramide seco-pseudonucleoside reagents.[2]
  • Botryolide B via esterification and ring-closing metathesis reaction.[3]
  • Pregnane derivatives containing γ-butyrolactones as potential glucocorticoid agonists.[4]

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCZ1686
MKBS9336V
MKBS3869V
MKBN6388V
MKBK8696V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Novel glucocorticoid antedrugs possessing a 21-(?-lactone) ring.
Angell RM, et al.
Journal of the Chemical Society. Perkin Transactions 1, 6, 831-839 (2002)
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-(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.
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)
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service