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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

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.
Name Type Language
BRASSIDIC ACID
MI  
Systematic Name English
(13E)-13-DOCOSENOIC ACID
Systematic Name English
13-DOCOSENOIC ACID, (13E)-
Common Name English
NSC-59686
Code 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 Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
NCI_THESAURUS C68440
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
Code System Code Type Description
FDA UNII
D23G5N92QR
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID601015913
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
PRIMARY
PUBCHEM
5282772
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
PRIMARY
CAS
506-33-2
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
PRIMARY
MERCK INDEX
m2639
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
PRIMARY Merck Index
NSC
59686
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
PRIMARY
NCI_THESAURUS
C68326
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
PRIMARY NCIT
ECHA (EC/EINECS)
208-035-5
Created by admin on Sat Dec 16 03:22:13 GMT 2023 , Edited by admin on Sat Dec 16 03:22:13 GMT 2023
PRIMARY