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Details

Stereochemistry ACHIRAL
Molecular Formula C12H8S3
Molecular Weight 248.387
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-TERTHIENYL

SMILES

S1C=CC=C1C2=CC=C(S2)C3=CC=CS3

InChI

InChIKey=KXSFECAJUBPPFE-UHFFFAOYSA-N
InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H

HIDE SMILES / InChI

Molecular Formula C12H8S3
Molecular Weight 248.387
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Alpha-Terthienyl is a pigment in African marigolds (Tagetes spp.) and exhibits antifungal, insecticidal, and nematicidal properties related to its ability to sensitize the formation of singlet oxygen. Terthiophene is the compound responsible for the insecticidal activity of Tagetes minuta. Alpha-Terthienyl is also used as building block in the production of organic semiconductors.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11412
Gene ID: 855480.0
Gene Symbol: ZWF1
Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Photoactivation of the nematicidal compound alpha-terthienyl from roots of marigolds (Tagetes species). A possible singlet oxygen role.
1979 Mar 25
Characterization of cutaneous phototoxicity induced by topical alpha-terthienyl and ultraviolet A radiation.
1986 Sep
Isolation of the insecticidal components of Tagetes minuta (Compositae) against mosquito larvae and adults.
1995 Sep
Pharmacokinetics, metabolism and toxicity of the plant-derived photoxin alpha-terthienyl.
1995 Sep
Novel protein kinase C inhibitors: alpha-terthiophene derivatives.
1998 Oct 6
Photodynamic inactivation of oropharyngeal Candida strains.
2014 Sep 25
Patents

Sample Use Guides

To investigate cutaneous UV phototoxicity 1% alpha-Terthienyl in 3% Azone gel was topically applied to mature female white guinea pigs. Investigators noted enhanced cutaneous phototoxicity with multiple applications; 3 per 24 hour period vs 1 per 24 hour period. The optimal interval between single drug application and irradiation was between 1-6 h to achieve maximum photosensitization. Clinical changes included mild erythema and inhibition of hair regrowth during the first 72 h after irradiation, with increasing erythema and edema progressing to erosion and crusting at 1 week. Clinical changes remained localized to the a-T -treated sites. Histopathologic changes at 72 h after irradiation paralleled macroscopic changes with crusting, subepidermal and intraepidermal edema and vesiculation, the presence of "sunburn" cells in the epidermis, and epidermal erosion ranging to complete epidermal degeneration.
Route of Administration: Topical
In Vitro Use Guide
32 microM alpha-Terthienyl was added to an emulsion of 1 micro-g/mL of glucose-6-phosphate dehydrogenase, from yeast, in a buffer of 0.1 M triethanolamine buffer, pH 7.6, and 1 g liter-’ of Tween 2O. Photooxidation was induced with UV radiation. Periodically 50 micro-L was extracted and assayed for glucose-6-phosphate dehydrogenase activity. Photoactivated alpha-terthienyl reduced glucose-6-phosphatase dehydrogenase by 76 and 97% after 36 and 90 minutes respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:11:28 GMT 2023
Edited
by admin
on Fri Dec 15 19:11:28 GMT 2023
Record UNII
0P77RAU2RR
Record Status Validated (UNII)
Record Version
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Name Type Language
.ALPHA.-TERTHIENYL
MI  
Common Name English
ALPHA-TERTHIOPHENE
Common Name English
TERTHIENYL, ALPHA-
Common Name English
.ALPHA.-TERTHIENYL [MI]
Common Name English
2,2':5'2''-TERTHIOPHENE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 74751
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
Code System Code Type Description
MERCK INDEX
m10587
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
PRIMARY Merck Index
CAS
1081-34-1
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
PRIMARY
MESH
C019101
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
PRIMARY
FDA UNII
0P77RAU2RR
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID2041206
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
PRIMARY
CHEBI
10335
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
PRIMARY
PUBCHEM
65067
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
PRIMARY
WIKIPEDIA
Terthiophene
Created by admin on Fri Dec 15 19:11:29 GMT 2023 , Edited by admin on Fri Dec 15 19:11:29 GMT 2023
PRIMARY