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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
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Quality Level

200

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[1].

Application

Diglycolic acid was used in the preparation of needle-like aragonite particles from calcium nitrate aqueous solutions[2].

Biochem/physiol Actions

Diglycolic acid has antithrombogenic properties and induces vasodilation[3]. It inhibits succinate dehydrogenase activity in human proximal tubule cells[4].

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
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
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
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