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Merck
CN

G6805

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

Key Documents

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Product Name

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

InChI

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

SMILES string

OC1COC(O)CO1

InChI key

ATFVTAOSZBVGHC-UHFFFAOYSA-N

form

crystalline

Quality Level

200

mp

85  °C

storage temp.

2-8°C

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB5127
SDBB1579
STBL2989
STBL1295
STBK8395

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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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