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Details

Stereochemistry ACHIRAL
Molecular Formula 2C22H42O2
Molecular Weight 677.1354
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of DIERUCIC ACID

SMILES

CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O

InChI

InChIKey=ZJVATSUMFCZSKA-QZOPMXJLSA-N
InChI=1S/2C22H42O2/c2*1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2*9-10H,2-8,11-21H2,1H3,(H,23,24)/b2*10-9-

HIDE SMILES / InChI

Molecular Formula C22H42O2
Molecular Weight 338.5677
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/4094523 | https://www.ncbi.nlm.nih.gov/pubmed/7979219 | https://www.ncbi.nlm.nih.gov/pubmed/28414112

Brassidic acid (22 carbon atoms) was first prepared from erucic acid by Reimer W. in 1886. It is a monounsaturated (one trans (E) double bond; shorthand nomenclature cannot be used to name trans fatty acids) fatty acid member of the sub-group called very long chain fatty acids (VLCFA), from 20 carbon atoms onwards, and is the trans-isomer of erucic acid. At a concentration of 0.1 mM, brassidic acid produced small increases in palmitoyl-CoA oxidation and carnitine acetyltransferase activities in hepatocytes cultured 70 hr.

Originator

Curator's Comment: Brassidic acid (22 carbon atoms) was first prepared from erucic acid by Reimer W. in 1886.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q704S8
Gene ID: 311849.0
Gene Symbol: Crat
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown

Sample Use Guides

500 mg/day
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Brassidic and erucic acids were overtly toxic to cultured rat hepatocytes when added to the culture medium at concentrations of 0.5 and 0.8 raM, respectively. Both acids produced extensive cell death and disruption of the cell monolayer within 24 hr, although the effects of brassidic acid were more severe than erucic ackt Cultures maintained for up to 96 hr with 0.1 or 0.2 mM brassidic acid showed a time~ and concentrationdependent increase in cell death; surviving cells appeared enlarged, with a more granular cytoplasm than the controls.
Hepatocytes were isolated from male Sprague-Dawley rats. Fatty acids initially were dissolved in serumfree culture medium containing 5% fatty acid-free bovine serum albumin (BSA) by stirring at 50 C and adding the minimum quantity of NaOH required to achieve a solution. These stock solutions (approximately 2-5 mM) were sterilized by passage through a 0.22 mkm filter. After deterruination of the actual fatty acid concentrations by gas liquid chromatography (GLC), stock solutions were diluted with culture medium. Hepatocytes were seeded at 2.5 x 10^6 viable cells per three ml culture medium (RPMI 1640 containing 5% fetal calf sermn, 50 mkg/ml gentamicin, 1 pM insulin and 0.1 mM hydrocortisone-21-sodium succinate) in 60 mm petri dishes and maintained at 37 C in a humidified atmosphere of 5% CO2/95% air. Exposure to fatty acids was commenced after two hr by replacing the culture medium with medium containing the fatty acids. Subsequently, the medium was changed and the cells were redosed every 24 hr.
Substance Class Chemical
Created
by admin
on Thu Jul 06 07:53:24 UTC 2023
Edited
by admin
on Thu Jul 06 07:53:24 UTC 2023
Record UNII
5ZOM04K2NR
Record Status Validated (UNII)
Record Version
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Name Type Language
DIERUCIC ACID
INCI  
INCI  
Official Name English
ERUCIC ACID DIMER
Common Name English
DIERUCIC ACID [INCI]
Common Name English
PRIPOL 1004
Brand Name English
13-DOCOSENOIC ACID, (Z)-, DIMER
Common Name English
13-DOCOSENOIC ACID, (13Z)-, DIMER
Common Name English
Code System Code Type Description
FDA UNII
5ZOM04K2NR
Created by admin on Thu Jul 06 07:53:24 UTC 2023 , Edited by admin on Thu Jul 06 07:53:24 UTC 2023
PRIMARY
PUBCHEM
71587217
Created by admin on Thu Jul 06 07:53:24 UTC 2023 , Edited by admin on Thu Jul 06 07:53:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID701021391
Created by admin on Thu Jul 06 07:53:24 UTC 2023 , Edited by admin on Thu Jul 06 07:53:24 UTC 2023
PRIMARY
CAS
63541-50-4
Created by admin on Thu Jul 06 07:53:24 UTC 2023 , Edited by admin on Thu Jul 06 07:53:24 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE