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Details

Stereochemistry ACHIRAL
Molecular Formula C22H42O2
Molecular Weight 338.5685
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ERUCIC ACID

SMILES

CCCCCCCC/C(/[H])=C(/[H])\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-

HIDE SMILES / InChI

Molecular Formula C22H42O2
Molecular Weight 338.5685
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

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
Screening for new compounds with antiherpes activity.
1984 Oct
Dietary erucic acid therapy for X-linked adrenoleukodystrophy.
1989 Nov
Requirements of dietary fats to meet nutritional needs & prevent the risk of atherosclerosis--an Indian perspective.
1998 Nov
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification.
2006 Jun
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 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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:04:14 UTC 2021
Edited
by admin
on Sat Jun 26 14:04:14 UTC 2021
Record UNII
075441GMF2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERUCIC ACID
HSDB   INCI   MI  
INCI  
Official Name English
NSC-6814
Code English
DOCOSENOIC ACID
Systematic Name English
NOURACID RE 07
Common Name English
PRIFRAC 2990
Common Name English
13Z-DOCOSENOIC ACID
Common Name English
13-CIS-DOCOSENOIC ACID
Common Name English
13-DOCOSENOIC ACID, (13Z)-
Common Name English
HYSTRENE 2290
Common Name English
ERUCIC ACID [HSDB]
Common Name English
22:1(N-9)
Code English
ERUCIC ACID [INCI]
Common Name English
JARIC 22:1
Common Name English
ERUCIC ACID [MI]
Common Name English
ERUCIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]
Common Name English
13-DOCOSENOIC ACID, (Z)-
Systematic Name English
.DELTA.13-CIS-DOCOSENOIC ACID
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68353
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
DSLD 3246 (Number of products:7)
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
Code System Code Type Description
FDA UNII
075441GMF2
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
MERCK INDEX
M5002
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY Merck Index
PUBCHEM
5281116
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
CAS
112-86-7
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
MESH
C049811
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
HSDB
5015
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
WIKIPEDIA
ERUCIC ACID
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
NCI_THESAURUS
C68364
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-011-3
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
EPA CompTox
112-86-7
Created by admin on Sat Jun 26 14:04:15 UTC 2021 , Edited by admin on Sat Jun 26 14:04:15 UTC 2021
PRIMARY
Related Record Type Details
LIPID -> FATTY ACID
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT