Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H42O2 |
Molecular Weight | 338.5677 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O
InChI
InChIKey=DPUOLQHDNGRHBS-KTKRTIGZSA-N
InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
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.tuscany-diet.net/lipids/list-of-fatty-acids/brassidic/ | https://www.ncbi.nlm.nih.gov/pubmed/4094523http://www.foodstandards.gov.au/publications/documents/Erucic%20acid%20monograph.pdfCurator'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.tuscany-diet.net/lipids/list-of-fatty-acids/brassidic/ | https://www.ncbi.nlm.nih.gov/pubmed/4094523http://www.foodstandards.gov.au/publications/documents/Erucic%20acid%20monograph.pdf
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
Erucic acid is a monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily biodegradable. Its high tolerance to temperature makes it suitable for transmission oil. Its ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:ln9) and erucic acid (22:1n9) have been found in the red blood cell membranes of autistic subjects with developmental regression. While studies done on laboratory animals in the early 1970s show that erucic acid appears to have toxic effects on the heart at high enough doses, an association between the consumption of rapeseed oil and increased myocardial lipidosis, or heart disease, has not been established for humans. While there are reports of toxicity from long-term use of Lorenzo's oil (which contains erucic acid and other ingredients), there are no reports of harm to people from dietary consumption of erucic acid. In 2003, Food Standards Australia set a provisional tolerable daily intake (PTDI) for an average adult of about 500 mg/day of erucic acid, extrapolated based on "the level that is associated with increased myocardial lipidosis in nursing pigs."
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 |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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Dietary erucic acid therapy for X-linked adrenoleukodystrophy. | 1989 Nov |
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Requirements of dietary fats to meet nutritional needs & prevent the risk of atherosclerosis--an Indian perspective. | 1998 Nov |
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Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization. | 2003 Oct 15 |
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Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. | 2006 Jun |
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Therapy of X-linked adrenoleukodystrophy. | 2008 Sep |
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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.
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.
Substance Class |
Chemical
Created
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Record UNII |
075441GMF2
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C68353
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DSLD |
3246 (Number of products:7)
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6814
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075441GMF2
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m5002
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5281116
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36031
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112-86-7
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C049811
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5015
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28792
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ERUCIC ACID
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C68364
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204-011-3
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DTXSID8026931
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Related Record | Type | Details | ||
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LIPID -> FATTY ACID |
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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