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Details

Stereochemistry ACHIRAL
Molecular Formula C12H20O4
Molecular Weight 228.2848
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TRAUMATIC ACID, (2Z)-

SMILES

OC(=O)CCCCCCCC\C=C/C(O)=O

InChI

InChIKey=MAZWDMBCPDUFDJ-CLFYSBASSA-N
InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7-

HIDE SMILES / InChI

Molecular Formula C12H20O4
Molecular Weight 228.2848
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Traumatic acid (TA) is a plant hormone (cytokinin) that in terms of chemical structure belongs to the group of fatty acids derivatives. It was isolated from Phaseolus vulgaris. It was discovered, that TA showed a stimulatory effect on antioxidative enzyme activity, reduced glutathione, thiol group content, and lipid peroxidation in physiological conditions. TA exhibited protective properties against ROS production. Thus, TA could be a potentially powerful agent with applications in the treatment of many skin diseases connected with oxidative stress and collagen biosynthesis disorders.

Originator

Curator's Comment: With his first postdoctoral fellow, James English, Jr., he isolated the active substance which called traumatic acid.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Traumatic Acid and Thiamin as Growth Factors for Algae.
1940 Jul 15
Inhibition of HIV-1 proteinase by non-peptide carboxylates.
1991 Apr 15
Traumatic Acid Reduces Oxidative Stress and Enhances Collagen Biosynthesis in Cultured Human Skin Fibroblasts.
2016 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Traumatic acid (TA) stimulated cell proliferation and biochemical processes connected with cell division, like: protein, nucleic acid and photosynthetic dye biosynthesis and photosynthesis intensity. TA could act in human cells, e.g., fibroblasts in the same way it acted at the molecular level in unsaturated fatty acids. Traumatic acid (TA) influence on tested parameters was examined in normal human skin fibroblasts in physiological conditions, without any stress factors. The fibroblast cell line was maintained in DMEM supplemented with 10 % FBS at 37 °C in a humified atmosphere of 5 % CO2 in air. Fibroblasts at a density of 1 × 105 cells/ml were incubated with or without the test compound in tissue culture in six-well plates in 2 ml of culture medium. The cell number was calculated at TA concentrations of 10−4, 10−5, 10−6 and 10−7 M. Collagen content in cells and medium, total protein content, SDS-PAGE and basic oxidative stress parameters such as: antioxidant enzyme activity, reduced glutathione and SH-group content and lipid peroxidation were studied at two TA concentrations: 10−5 and 10−6 M.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:36:26 GMT 2023
Edited
by admin
on Sat Dec 16 09:36:26 GMT 2023
Record UNII
063FSX662R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRAUMATIC ACID, (2Z)-
Common Name English
TRAUMATIC ACID CIS-FORM
MI  
Common Name English
2-DODECENEDIOIC ACID, (2Z)-
Systematic Name English
CIS-TRAUMATIC ACID
Systematic Name English
TRAUMATIC ACID CIS-FORM [MI]
Common Name English
Code System Code Type Description
CAS
6556-35-0
Created by admin on Sat Dec 16 09:36:26 GMT 2023 , Edited by admin on Sat Dec 16 09:36:26 GMT 2023
PRIMARY
FDA UNII
063FSX662R
Created by admin on Sat Dec 16 09:36:26 GMT 2023 , Edited by admin on Sat Dec 16 09:36:26 GMT 2023
PRIMARY
MERCK INDEX
m11007
Created by admin on Sat Dec 16 09:36:26 GMT 2023 , Edited by admin on Sat Dec 16 09:36:26 GMT 2023
PRIMARY Merck Index
PUBCHEM
5354373
Created by admin on Sat Dec 16 09:36:26 GMT 2023 , Edited by admin on Sat Dec 16 09:36:26 GMT 2023
PRIMARY