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857297

Sigma-Aldrich

D-(+)-Ribonic γ-lactone

97%

Synonym(s):

D(+)-Ribono-1,4-lactone

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About This Item

Empirical Formula (Hill Notation):
C5H8O5
CAS Number:
5336-08-3
Molecular Weight:
148.11
Beilstein:
82057
EC Number:
226-256-5
MDL number:
MFCD00063241
UNSPSC Code:
12352202
PubChem Substance ID:
24888436
NACRES:
NA.22

Quality Level

200

Assay

97%

form

crystals

optical activity

[α]24/D +18°, c = 1 in H2O

mp

85-87 °C (lit.)

SMILES string

OC[C@H]1OC(=O)[C@H](O)[C@@H]1O

InChI

1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4-/m1/s1

InChI key

CUOKHACJLGPRHD-BXXZVTAOSA-N

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Application

Important building block for chiral acyclics, cyclopentenones, and oxabicyclic systems. Also employed in studies on nonlinear optical materials.

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

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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Aldrichimica Acta, 22, 49-49 (1989)
Chemistry of Materials, 5, 802-802 (1993)
Jan-Moritz Sutter et al.
FEMS microbiology letters, 364(13) (2017-09-01)
Haloferax volcanii degrades the pentoses D-xylose and L-arabinose via an oxidative pathway to α-ketoglutarate as an intermediate. The initial dehydrogenases of the pathway, D-xylose dehydrogenase (XDH) and L-arabinose dehydrogenase (L-AraDH) catalyze the NADP+ dependent D-xylose and L-arabinose oxidation. It is
Cheng-Hung Jen et al.
Nucleosides, nucleotides & nucleic acids, 29(7), 523-534 (2010-07-01)
A thorough study for the synthesis of 1-deazauridine is described. 3-Bromo-2,6-dimethoxy-5-(beta-D-ribofuranosyl)pyridine, a synthetic precursor for 1-deazauridine, was prepared in seven steps from 2,6-dimethoxypyridine and d-ribose via the ribonolactone approach. Subsequent demethylation was unsuccessful but led to presumable anomerization and isomerization.
Virginie Faure et al.
Biochemical and biophysical research communications, 328(4), 1188-1195 (2005-02-15)
Free radical attack on the sugar-phosphate backbone generates oxidized apurinic/apyrimidinic (AP) residues in DNA. 2'-deoxyribonolactone (dL) is a C1'-oxidized AP site damage generated by UV and gamma-irradiation, and certain anticancer drugs. If not repaired dL produces G-->A transitions in Escherichia
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