U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H16O4
Molecular Weight 296.3172
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COCAIC ACID

SMILES

OC(=O)[C@H]1[C@@H]([C@@H]([C@H]1C2=CC=CC=C2)C(O)=O)C3=CC=CC=C3

InChI

InChIKey=QWFRRFLKWRIKSZ-BIAGXBKMSA-N
InChI=1S/C18H16O4/c19-17(20)15-13(11-7-3-1-4-8-11)16(18(21)22)14(15)12-9-5-2-6-10-12/h1-10,13-16H,(H,19,20)(H,21,22)/t13-,14-,15-,16-

HIDE SMILES / InChI

Molecular Formula C18H16O4
Molecular Weight 296.3172
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

alpha-truxillic acid (also known as cocaic acid) shows significant anti-inflammatory activities as indicated by the formalin test in mice. While certain derivatives of alpha-truxillic acid can directly activate peroxisome proliferator-activated receptor gamma, alpha -truxillic acid has no such activity.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Comparative sensitivity of neuro-muscular synapses of different muscles toward d-tubocurarine chloride and alpha-truxillic acid].
1967 Mar-Apr
Antinociceptive activities of alpha-truxillic acid and beta-truxinic acid derivatives.
2006 Mar
Solid-state photodimerization kinetics of alpha-trans-cinnamic acid to alpha-truxillic acid studied via solid-state NMR.
2006 Mar 30
Kinetics of the single-crystal to single-crystal two-photon photodimerization of alpha-trans-cinnamic acid to alpha-truxillic acid.
2009 Apr 2
Patents

Patents

Sample Use Guides

Male ddy mice were used. The test drug (alpha-truxillic acid (40mg/kg)) was prepared as suspensions with 0.5% Tween 80/saline and intraperitoneally administered 10 min prior to the injection of an inducer (1% formalin/saline, 20l). The mice were observed for 30 min and the time that the mice spent licking the injected right hindpaw was recorded. The nociceptive scores normally peaked 0 to 10min after formalin injection (early phase) and 10 to 30min (late phase) after the injection, representing the neurogenic and inflammatory pain responses, respectively. The time spent licking the injected paw was recorded and the data were expressed as total licking time in the early phase and late phase.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 06:39:22 GMT 2023
Edited
by admin
on Sat Dec 16 06:39:22 GMT 2023
Record UNII
821BB4R21V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COCAIC ACID
Common Name English
1,3-CYCLOBUTANEDICARBOXYLIC ACID, 2,4-DIPHENYL-, (1.ALPHA.,2.ALPHA.,3.BETA.,4.BETA.)-
Common Name English
TRUXILLIC ACID [MI]
Common Name English
TRUXILLIC ACID .ALPHA.-ISOMER
MI  
Common Name English
NSC-103001
Code English
.ALPHA.-TRUXILLIC ACID
Common Name English
TRUXILLIC ACID, .ALPHA.-ISOMER
Common Name English
GRATISSIMIC ACID
Common Name English
Code System Code Type Description
MERCK INDEX
m11241
Created by admin on Sat Dec 16 06:39:22 GMT 2023 , Edited by admin on Sat Dec 16 06:39:22 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
224-724-3
Created by admin on Sat Dec 16 06:39:22 GMT 2023 , Edited by admin on Sat Dec 16 06:39:22 GMT 2023
PRIMARY
PUBCHEM
78213
Created by admin on Sat Dec 16 06:39:22 GMT 2023 , Edited by admin on Sat Dec 16 06:39:22 GMT 2023
PRIMARY
CAS
4462-95-7
Created by admin on Sat Dec 16 06:39:22 GMT 2023 , Edited by admin on Sat Dec 16 06:39:22 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
CAS
490-20-0
Created by admin on Sat Dec 16 06:39:22 GMT 2023 , Edited by admin on Sat Dec 16 06:39:22 GMT 2023
PRIMARY
WIKIPEDIA
Truxillic acid
Created by admin on Sat Dec 16 06:39:22 GMT 2023 , Edited by admin on Sat Dec 16 06:39:22 GMT 2023
PRIMARY
FDA UNII
821BB4R21V
Created by admin on Sat Dec 16 06:39:22 GMT 2023 , Edited by admin on Sat Dec 16 06:39:22 GMT 2023
PRIMARY
NSC
103001
Created by admin on Sat Dec 16 06:39:22 GMT 2023 , Edited by admin on Sat Dec 16 06:39:22 GMT 2023
PRIMARY