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49920

Sigma-Aldrich

Glycerol formal

≥98.0% (GC)

Synonym(s):

1,3(or 2,3)-O-Methylene-1,2,3-propanetriol

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About This Item

Empirical Formula (Hill Notation):
C4H8O3
CAS Number:
99569-11-6
Molecular Weight:
104.10
Beilstein/REAXYS Number:
103206
MDL number:
MFCD10039829
UNSPSC Code:
12352100
PubChem Substance ID:
57651229
NACRES:
NA.22

assay

≥98.0% (GC)

contains

~0.02% 2,6-di-tert-butyl-4-methylphenol as stabilizer

composition

5-hydroxy-1,3-dioxane, ~60%
4-hydroxymethyl-1,3-dioxolane, ~40%

refractive index

n20/D 1.451 (lit.)
n20/D 1.451

bp

192-193 °C (lit.)

density

1.203 g/mL at 25 °C (lit.)

functional group

ether
hydroxyl

SMILES string

OCC1COCO1.OC2COCOC2

InChI

1S/2C4H8O3/c5-4-1-6-3-7-2-4;5-1-4-2-6-3-7-4/h2*4-5H,1-3H2

InChI key

JIUMSISXCKWZTA-UHFFFAOYSA-N

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General description

Glycerol formal (GF) is a light glycerol acetal that is composed of ~60% 5-hydroxy-1,3-dioxane and ~40% 4-hydroxymethyl-1,3-dioxolane. It can be prepared by reacting glycerol and formaldehyde in the presence of acid catalyst. The potential of GF as an injection solvent for use in toxicity testing has been reported.

Application

Glycerol formal is used to to solubilize water-insoluble compounds for subsequent aqueous dilution. It has been used as a chemical and dye emulsifier and as a cosolvent for drug delivery. Glycerol formal was used as a vehicle for antibiotic delivery in rats.
Glycerol formal may be used in the multi-step synthesis of 9-[(2-hydroxy-1-(hydroxymethyl)ethoxy)methyl]guanine (2′-nor-2′-deoxyguanosine), an analog of acyclovir. It may be used in the preparation of 4-substituted dioxolanes.

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9738
BCCH0475
BCCD7726
BCBQ8227V
BCBR2384V

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A note on glycerol formal as a solvent in toxicity testing.
Sanderson DM.
The Journal of Pharmacy and Pharmacology, 11(1), 150-156 (1959)
4-Substituted dioxolanes by chemoselective reactions on glycerol formal.
Gras JL, et al.
Tetrahedron Letters, 34(27), 4335-4336 (1993)
Activation by thymidine kinase and potent antiherpetic activity of 2'-nor-2'-deoxyguanosine (2' NDG).
Ashton WT, et al.
Biochemical and Biophysical Research Communications, 108(4), 1716-1721 (1982)
Selective catalytic etherification of glycerol formal and solketal with dialkyl carbonates and K2CO3.
Selva M, et al.
Green Chemistry, 14(1), 188-200 (2012)
Sarah Nickolls et al.
Advances in pharmacological sciences, 2011, 608912-608912 (2011-12-14)
GABA(A) receptors containing α2/3 subunits are current targets in the battle to develop new pain medications, as they are expressed in the spinal cord where increasing inhibitory drive should result in analgesia. However, this approach is prone to a range
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