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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 ERUCIC ACID

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-

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
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

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 Fri Dec 15 19:00:09 GMT 2023
Edited
by admin
on Fri Dec 15 19:00:09 GMT 2023
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 Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
DSLD 3246 (Number of products:7)
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
Code System Code Type Description
NSC
6814
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
FDA UNII
075441GMF2
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
MERCK INDEX
m5002
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY Merck Index
PUBCHEM
5281116
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
CHEBI
36031
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
CAS
112-86-7
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
MESH
C049811
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
HSDB
5015
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
CHEBI
28792
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
WIKIPEDIA
ERUCIC ACID
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
NCI_THESAURUS
C68364
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-011-3
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID8026931
Created by admin on Fri Dec 15 19:00:09 GMT 2023 , Edited by admin on Fri Dec 15 19:00:09 GMT 2023
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