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143073

Sigma-Aldrich

Diglycolic acid

98%

Synonym(s):

2,2′-Oxydiacetic acid

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About This Item

Linear Formula:
O(CH2COOH)2
CAS Number:
110-99-6
Molecular Weight:
134.09
Beilstein:
1072117
EC Number:
203-823-5
MDL number:
MFCD00004309
UNSPSC Code:
12352100
PubChem Substance ID:
24848573
NACRES:
NA.22

Assay

98%

mp

140-144 °C (lit.)

solubility

ethanol: soluble 5%, clear to slightly hazy, colorless to greenish-yellow

functional group

carboxylic acid
ether

SMILES string

OC(=O)COCC(O)=O

InChI

1S/C4H6O5/c5-3(6)1-9-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

InChI key

QEVGZEDELICMKH-UHFFFAOYSA-N

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General description

Diglycolic acid is a toxic metabolite of diethylene glycol (DEG) responsible for DEG-induced proximal tubular necrosis.

Application

Diglycolic acid was used in the preparation of needle-like aragonite particles from calcium nitrate aqueous solutions.

Biochem/physiol Actions

Diglycolic acid has antithrombogenic properties and induces vasodilation. It inhibits succinate dehydrogenase activity in human proximal tubule cells.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW1943
MKCW3352
MKCV5211
MKCV5212
MKCW9684

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Miriam E Mossoba et al.
Toxicology in vitro : an international journal published in association with BIBRA, 52, 87-93 (2018-06-12)
Carboxymethyl starches are added to food products for thickening or tablet binding/filling purposes. Although they lack toxicity, their synthesis creates the chemical byproduct diglycolic acid (DGA), which is difficult to eliminate and whose toxicity is in question. A rare case
Zahraa Youssef et al.
Photodiagnosis and photodynamic therapy, 22, 115-126 (2018-03-28)
In this study, light-sensitive photosensitizers (Chlorin e6, Ce6) were linked to TiO2 and SiO2 nanoparticles (NPs) in order to develop new kinds of NP-based drug delivery systems for cancer treatment by PDT. TiO2 or SiO2 NPs were modified either by
Ming-Ming Yu et al.
Journal of pharmaceutical and biomedical analysis, 85, 21-27 (2013-07-23)
Controlling and minimizing the adverse effects of drugs are the key issues in ensuring the safety of drug therapy. Carboxymethyl chitosan has been widely used as an anti-adhesion material. However, recently in China there have been several reported instances of
Preparation of needle-like aragonite particles from calcium nitrate solution.
Fellner P, et al.
Acta Chimica Slovenica, 4(2), 3-10 (2011)
Greg M Landry et al.
Toxicology letters, 221(3), 176-184 (2013-07-06)
Diethylene glycol (DEG) is a solvent used in consumer products allowing the increased risk for consumer exposure. DEG metabolism produces two primary metabolites, 2-hydroxyethoxyacetic acid (2-HEAA) and diglycolic acid (DGA). DGA has been shown to be the toxic metabolite responsible
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