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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
Structure of BRASSIDIC ACID

SMILES

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

InChI

InChIKey=DPUOLQHDNGRHBS-MDZDMXLPSA-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+

HIDE SMILES / InChI

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

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."

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
PubMed

PubMed

TitleDatePubMed
Further evaluation of a novel nano-scale gene vector for in vivo transfection of siRNA.
2011-05
Therapy of X-linked adrenoleukodystrophy.
2008-09
Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification.
2006-06
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003-10-15
Requirements of dietary fats to meet nutritional needs & prevent the risk of atherosclerosis--an Indian perspective.
1998-11
Dietary erucic acid therapy for X-linked adrenoleukodystrophy.
1989-11
Screening for new compounds with antiherpes activity.
1984-10
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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.
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.
Name Type Language
NSC-59686
Preferred Name English
BRASSIDIC ACID
MI  
Systematic Name English
(13E)-13-DOCOSENOIC ACID
Systematic Name English
13-DOCOSENOIC ACID, (13E)-
Common Name English
(E)-13-DOCOSENOIC ACID
Systematic Name English
TRANS-13-DOCOSENOIC ACID
Systematic Name English
BRASSIDIC ACID [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68353
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
NCI_THESAURUS C68440
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
Code System Code Type Description
FDA UNII
D23G5N92QR
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID601015913
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
PRIMARY
PUBCHEM
5282772
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
PRIMARY
CAS
506-33-2
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
PRIMARY
MERCK INDEX
m2639
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
PRIMARY Merck Index
NSC
59686
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
PRIMARY
NCI_THESAURUS
C68326
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
PRIMARY NCIT
ECHA (EC/EINECS)
208-035-5
Created by admin on Mon Mar 31 21:18:23 GMT 2025 , Edited by admin on Mon Mar 31 21:18:23 GMT 2025
PRIMARY