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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/REAXYS Number:
506029
MDL number:
MFCD00012133
UNSPSC Code:
12352100
PubChem Substance ID:
24895276
NACRES:
NA.22

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)
1, 2-bis (2-hydroxyethyl) hydrazine and derivatives.
Nielsen AT
The Journal of Organic Chemistry, 42(17), 2900-2902 (1977)
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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
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