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310301

Sigma-Aldrich

L-Gulonic acid γ-lactone

95%

Synonym(s):

L-Gulonic γ-lactone, L-(+)-Gulono-1,4-lactone

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About This Item

Empirical Formula (Hill Notation):
C6H10O6
CAS Number:
Molecular Weight:
178.14
Beilstein:
83002
MDL number:
UNSPSC Code:
12352106
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

Application

  • Development and validation of an analysis method: Discusses the use of L-gulonic acid γ-lactone as a matrix effect inhibitor in the validation of a method for pesticide residues by gas chromatography–tandem mass spectrometry (Saegusa, Nomura, Takao, Hamaguchi, 2021).

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.
J Hajkó et al.
Carbohydrate research, 321(1-2), 116-120 (1999-12-28)
An efficient method for the synthesis of L-glucose from D-gulono-1,4-lactone via 1,2,3,4,5-penta-O-benzyl/acetyl/benzoyl-D-gulitol is described in 34-53% overall yield.
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

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