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Details

Stereochemistry ACHIRAL
Molecular Formula C24H48O2
Molecular Weight 368.6367
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIGNOCERIC ACID

SMILES

CCCCCCCCCCCCCCCCCCCCCCCC(O)=O

InChI

InChIKey=QZZGJDVWLFXDLK-UHFFFAOYSA-N
InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula C24H48O2
Molecular Weight 368.6367
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Lignoceric Acid (tetracosanoic acid) is a saturated fatty acid with a 24-carbon backbone, that occurs naturally in wood tar, various cerebrosides, and in small amount in most natural fats. In mammals, it is found in cerebrosides and is synthesized during brain development. The deficient peroxisomal oxidation of very-long-chain fatty acids, including lignoceric acid, contributes to certain syndromes, including Zellweger cerebro-hepato-renal syndrome and X chromosome-linked adrenoleukodystrophy. Lignoceric acid is also a product of lignin production.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown
Diagnostic
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Oral
In Vitro Use Guide
Human skin fibroblasts were used for activity evaluation. Cell cultures were washed twice with serum-free DMEM F-12 and cultured for another 24 h in DMEM F-12 (supplemented with 1% FBS) medium before treatment with VLCFAs. Varying concentrations (0.5–10 mg/ml) of lignoceric acid (a 24-carbon compound) or cerotic acid (a 26-carbon compound) were added to the cell cultures and cells were further cultured for 48 h. Culture medium containing VLCFAs was changed once after 24 h. of treatment and replaced with fresh culture medium containing the same concentrations of VLCFAs as originally added. NADPH oxidase (NOX) activity was measured in cell homogenates at 37C using lucigenin and NADPH. Enzymic activity of NOX was significantly ( p<0.001) increased in dermal fibroblasts following treatment with lignoceric acid or cerotic acid.
Substance Class Chemical
Record UNII
RK3VCW5Y1L
Record Status Validated (UNII)
Record Version