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G6805

Sigma-Aldrich

Glycolaldehyde dimer

crystalline, mixture of stereoisomers. Melts between 80 and 90 °C depending on stereoisomeric composition

Synonym(s):

1,4-Dioxane-2,5-diol, 2,5-Dihydroxy-1,4-dioxane, Hydroxyacetaldehyde dimer

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About This Item

Empirical Formula (Hill Notation):
C4H8O4
CAS Number:
23147-58-2
Molecular Weight:
120.10
Beilstein:
506029
MDL number:
MFCD00012133
UNSPSC Code:
12352100
PubChem Substance ID:
24895276
NACRES:
NA.22

Quality Level

200

form

crystalline

storage temp.

2-8°C

SMILES string

OC1COC(O)CO1

InChI

1S/C4H8O4/c5-3-1-7-4(6)2-8-3/h3-6H,1-2H2

InChI key

ATFVTAOSZBVGHC-UHFFFAOYSA-N

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Application

Glycolaldehyde dimer may be used in the synthesis of 3,4-diaza-2-hexene-1,6-diol, which can undergo hydrogenation to form 1,2-bis(2-hydroxyethyl)hydrazine. It undergoes cycloaddition with 2,3-dihydrofuran in the presence of a chiral catalyst to form fused bicyclic tetrahydrofuran (bis-THF) alcohol, a key moiety of HIV protease inhibitors.

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)

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Hydroxyacetone contains ≤500 ppm sodium carbonate as stabilizer, technical grade, 90%

Sigma-Aldrich

138185

Hydroxyacetone

Efficient Synthesis of (3 R, 3a S, 6a R)-Hexahydrofuro [2, 3-b] furan-3-ol from Glycolaldehyde.
Canoy WL
Organic Letters, 10(6), 1103-1106 (2008)
Hiromi Niwa et al.
Journal of natural medicines, 75(1), 194-200 (2020-09-26)
The production and accumulation of advanced glycation end products (AGEs) have been implicated in diabetes and diabetic complication. This study was conducted as a search for an AGE inhibitor from brown alga, Sargassum macrocarpum. Separation and purification were performed using
1, 2-bis (2-hydroxyethyl) hydrazine and derivatives.
Nielsen AT
The Journal of Organic Chemistry, 42(17), 2900-2902 (1977)
Sander De Bruyne et al.
Journal of clinical medicine, 9(9) (2020-09-10)
Age-related macular degeneration is the leading cause of blindness in the developed world. Since advanced glycation end products (AGEs) are implicated in the pathogenesis of AMD through various lines of evidence, we investigated the potential of fructosamine-3-kinase (FN3K) in the
Stéphan Houdier et al.
Analytical and bioanalytical chemistry, 410(27), 7031-7042 (2018-08-11)
Derivatization techniques based on α-effect amines and H+ catalysis are commonly used for the measurement of carbonyl compounds (CCs), whether in environmental, food, or biological samples. Here, we investigated the potential of aniline-based catalysts to improve derivatization rates of selected
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