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310301

Sigma-Aldrich

L-Gulonic acid γ-lactone

95%

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Synonym(s):
L-Gulonic γ-lactone, L-(+)-Gulono-1,4-lactone
Empirical Formula (Hill Notation):
C6H10O6
CAS Number:
Molecular Weight:
178.14
Beilstein:
83002
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

solid

optical activity

[α]19/D +55°, c = 4 in H2O

mp

187-190 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1

InChI key

SXZYCXMUPBBULW-SKNVOMKLSA-N

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This Item
34742579469471429
Gluconolactone An oxidation product of glucose by glucose oxidase.

Millipore

347425

Gluconolactone

D-Arabino-1,4-lactone ≥97.0% (HPLC)

Sigma-Aldrich

79469

D-Arabino-1,4-lactone

form

solid

form

solid

form

crystals

form

solid

mp

187-190 °C (lit.)

mp

-

mp

94 - 100  °C ( (201 - 212 °F ))

mp

225 °C (dec.) (lit.)

storage temp.

2-8°C

storage temp.

15-25°C

storage temp.

−20°C

storage temp.

2-8°C

optical activity

[α]19/D +55°, c = 4 in H2O

optical activity

-

optical activity

[α]/D 72.0±3.0°, c = 1 in H2O

optical activity

[α]20/D −21°, c = 1 in H2O

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

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Beata A Wolucka et al.
The FEBS journal, 273(19), 4435-4445 (2006-09-08)
The last step of the biosynthesis of L-ascorbic acid (vitamin C) in plants and animals is catalyzed by L-gulono-1,4-lactone oxidoreductases, which use both L-gulono-1,4-lactone and L-galactono-1,4-lactone as substrates. L-gulono-1,4-lactone oxidase is missing in scurvy-prone, vitamin C-deficient animals, such as humans
Tsuyoshi Imai et al.
Physiologia plantarum, 136(2), 139-149 (2009-05-21)
The L-ascorbate (AsA) content and the expression of six L-galactose pathway-related genes were analyzed in peach flesh during fruit development. Fluctuation of AsA during peach fruit development was divided into four phases based on the overall total AsA (T-AsA) content
Prashantha Gunaga et al.
Organic letters, 8(19), 4267-4270 (2006-09-08)
Stereoselective synthesis of novel 1'-alpha-substituted-4'-thionucleosides was achieved starting from D-gulonic acid gamma-lactone via stereoselective nucleophilic substitution.
G Bánhegyi et al.
FEBS letters, 381(1-2), 39-41 (1996-02-26)
Ascorbate synthesis causes glutathione consumption in the liver. Addition of gulonolactone resulted in an increase of ascorbate production in isolated murine hepatocytes. At the same time, a decrease in reduced glutathione (GSH) level was observed. In hepatic microsomal membranes, ascorbate
F Puskás et al.
FEBS letters, 430(3), 293-296 (1998-08-04)
The orientation of gulonolactone oxidase activity was investigated in rat liver microsomes. Ascorbate formation upon gulonolactone addition resulted in higher intravesicular than extravesicular ascorbate concentrations in native microsomal vesicles. The intraluminal ascorbate accumulation could be prevented or the accumulated ascorbate

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