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
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-
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 |
DescriptionSources: http://www.foodstandards.gov.au/publications/documents/Erucic%20acid%20monograph.pdfhttp://www.tuscany-diet.net/lipids/list-of-fatty-acids/brassidic/ | https://www.ncbi.nlm.nih.gov/pubmed/4094523Curator'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
Sources: http://www.foodstandards.gov.au/publications/documents/Erucic%20acid%20monograph.pdfhttp://www.tuscany-diet.net/lipids/list-of-fatty-acids/brassidic/ | https://www.ncbi.nlm.nih.gov/pubmed/4094523
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q704S8 Gene ID: 311849.0 Gene Symbol: Crat Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/4094523 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Screening for new compounds with antiherpes activity. | 1984 Oct |
|
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization. | 2003 Oct 15 |
|
Therapy of X-linked adrenoleukodystrophy. | 2008 Sep |
|
Further evaluation of a novel nano-scale gene vector for in vivo transfection of siRNA. | 2011 May |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4094523
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
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Sat Dec 16 01:36:01 GMT 2023
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Record UNII |
5ZOM04K2NR
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Record Status |
Validated (UNII)
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Record Version |
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71587217
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63541-50-4
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