444286
(R)-(+)-α-Hydroxy-γ-butyrolactone
95%, optical purity ee: 98% (GLC)
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Synonym(s):
(R)-4,5-Dihydro-3-hydroxy-2(3H)-furanone
Empirical Formula (Hill Notation):
C4H6O3
CAS Number:
Molecular Weight:
102.09
Beilstein:
80588
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
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
Related Categories
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.
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)
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.
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)
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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