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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:
1128-23-0
Molecular Weight:
178.14
Beilstein:
83002
MDL number:
MFCD00064331
UNSPSC Code:
12352106
PubChem Substance ID:
24858787
NACRES:
NA.22

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

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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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
Marjan Jeselnik et al.
Organic letters, 5(15), 2651-2653 (2003-07-19)
[reaction: see text] A new synthesis of L-noviose (11), a sugar moiety of novobiocin, is presented. D-Gulonolactone was initially converted in a few steps to the key ester derivative 7 [1-O-benzyl methyl 2,3-O-(1-methylethylidene)-alpha-L-lyxofuranosiduronate]. An appropriate selection of protecting groups enabled
G W Fleet et al.
Carbohydrate research, 205, 269-282 (1990-09-19)
The synthesis of the enantiomers of 6-epicastanospermine and of 1,6-diepicastanospermine from the enantiomeric gulonolactones is reported and the structure of the former is established as (1S,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxyoctahydroindolizine. The inhibitory activities of the diastereomers against the amyloglucosidase-catalysed hydrolysis of p-nitrophenyl alpha-D-glucopyranoside were
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
A Krasnov et al.
Genetic analysis : biomolecular engineering, 15(3-5), 115-119 (1999-12-22)
The reviewed studies addressed the possibility of using gene transfer for correction of L-ascorbic acid biosynthesis and carbohydrate utilization in rainbow trout. Analyses of enzymatic activities in the L-AAB pathway indicated that reasons for the lack of L-AA production can
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