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Details

Stereochemistry ACHIRAL
Molecular Formula C10H18O4
Molecular Weight 202.2475
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIBUTYL OXALATE

SMILES

CCCCOC(=O)C(=O)OCCCC

InChI

InChIKey=JKRZOJADNVOXPM-UHFFFAOYSA-N
InChI=1S/C10H18O4/c1-3-5-7-13-9(11)10(12)14-8-6-4-2/h3-8H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C10H18O4
Molecular Weight 202.2475
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Dibutyl oxalate is used in the manufacture of lubricants is biologically toxic causing neurological degradation characterized by ataxia and stupor. Sufficient dosing of dibutyl oxalate induces oxalate retinopathy, an experimental model of "flecked retina". In this model, the retinal flecks are the result of an intracellular accumulation of calcium oxalate in the RPE cells.

CNS Activity

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Male Dutch rabbits were treated with injections of 1.0, 2.0, and 4.0 mL of dibutyl oxalate and an equivalent volume of 0.5 M calcium chloride solution administered subcutaneously at a second injection site. Ophthalmoscopic observations were carried out on all animals prior to the first injection and on a daily basis thereafter. Animals were killed at 20 days or when signs of neurological impairment such as ataxia and stupor appeared. Animals treated with 1.0 mL of dibutyl oxalate showed few toxic signs and were killed at 20 days. Two of the five animals receiving 2.0 mL of dibutyl oxalate survived four and five days, respectively; the remaining three were killed at 20 days. The five animals receiving 4.0 mL died within three days, all exhibiting terminal signs of ataxia and stupor. A total of ten treated rabbits survived 3 days or more. Seven of these exhibited a "flecked retina"appearance o the fundus prior to death, and the clinical and pathologic findings in these animals were more extensive in those that survived up to 20 days. Histopathological examination revealed that the seven rabbits with flecked retinals demonstrated intracellular needle-like crystals within numerous cells of the RPE.
Route of Administration: Parenteral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
S18C168OWC
Record Status Validated (UNII)
Record Version