Accéder au contenu
Merck
Toutes les photos(1)

Key Documents

View All Documentation

T4540

Sigma-Aldrich

Triacsin C from Streptomyces sp.

Synonyme(s) :

2,4,7-Undecatrienal nitrosohydrazone, WS1228A

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(1)

About This Item

Formule empirique (notation de Hill):
C11H17N3O
Numéro CAS:
76896-80-5
Poids moléculaire :
207.27
Numéro MDL:
MFCD00798237
Code UNSPSC :
51111800
ID de substance PubChem :
24900214
Nomenclature NACRES :
NA.77

Source biologique

Streptomyces sp.

Niveau de qualité

200

Forme

powder

Solubilité

methanol: soluble 4.90-5.10 mg/mL, clear (Pale yellow to yellow)
methanol: soluble 4.90-5.10 mg/mL, clear, pale yellow to yellow

Mode d’action

enzyme | inhibits

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

CCC\C=C\C\C=C\C=C\C=N\NN=O

InChI

1S/C11H17N3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h4-5,7-11H,2-3,6H2,1H3,(H,13,15)/b5-4+,8-7+,10-9+,12-11+

Clé InChI

NKTGCVUIESDXPU-YLEPRARLSA-N

Description générale

Triacsin C belongs to a family of fungal metabolites all having an 11-carbon alkenyl chain with a common N-hydroxytriazene moiety at the terminus.

Application

Triacsin C was found to induce maturation in mouse and Xenopus oocytes in the absence of long-chain acyl-CoA synthetase. Triacsin C can also block palmitoylation of the G-protein alpha S subunit6. Furthermore, triacsin C can stabilize1-oleoyl-2-acetyl-sn-glycerol (OAG) and enhance perilipin 3 recruitment to the endoplasmic reticulum (ER) in mouse cells7.

Actions biochimiques/physiologiques

Triacsin C is a potent inhibitor of long-chain fatty acyl CoA synthetase. It blocks β-cell apoptosis, induced by fatty acids (lipoapoptosis) in a rat model of obesity. In addition, it blocks the de novo synthesis of triglycerides, diglycerides, and cholesterol esters, thus interfering with lipid metabolism.

Notes préparatoires

Triacsin C is soluble in methanol at 4.90 - 5.10 mg/ml and yields a clear, pale yellow to yellow solution.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Y-L Xie et al.
Theriogenology, 78(9), 1917-1928 (2012-10-13)
In vivo and in vitro approaches were used to elucidate mechanisms of palmitate-induced cytotoxicity of follicle granulosa cells in fuel-overloaded broiler hens. In contrast to their energy-restricted counterparts, broiler breeder hens fed ad libitum for 2 wk had dyslipidemia, atresia
Yulia Y Tyurina et al.
FEBS letters, 586(3), 235-241 (2012-01-03)
Peroxidation of cardiolipin in mitochondria is essential for the execution of apoptosis. We suggested that integration of oleic acid into cardiolipin generates non-oxidizable cardiolipin species hence protects cells against apoptosis. We synthesized mitochondria-targeted triphenylphosphonium oleic acid ester. Using lipidomics analysis
M Shimabukuro et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(16), 9558-9561 (1998-08-05)
Obesity causes its complications through functional and morphologic damage to remotely situated tissues via undetermined mechanisms. In one rodent model of obesity, the Zucker diabetic fatty fa/fa rat, overaccumulation of triglycerides in the pancreatic islets may be responsible for a
R A Igal et al.
The Biochemical journal, 324 ( Pt 2), 529-534 (1997-06-01)
The trafficking of acyl-CoAs within cells is poorly understood. In order to determine whether newly synthesized acyl-CoAs are equally available for the synthesis of all glycerolipids and cholesterol esters, we incubated human fibroblasts with [14C]oleate, [3H]arachidonate or [3H]glycerol in the
Sanjay Basak et al.
Prostaglandins, leukotrienes, and essential fatty acids, 88(2), 155-162 (2012-11-17)
Fatty acids regulate angiogenesis although no such information is available in first trimester placental trophoblast cells despite the fact that angiogenesis is a critical step involving these cells in early placentation. We investigated effects of different fatty acids on angiogenesis
Afficher tous les articles scientifiques apparentés

Articles

Discover Bioactive Small Molecules for Lipid Signaling Research

Discover Bioactive Small Molecules for Lipid Signaling Research

Discover Bioactive Small Molecules for Lipid Signaling Research

Discover Bioactive Small Molecules for Lipid Signaling Research

Discover Bioactive Small Molecules for Lipid Signaling Research

Discover Bioactive Small Molecules for Lipid Signaling Research

Discover Bioactive Small Molecules for Lipid Signaling Research

Discover Bioactive Small Molecules for Lipid Signaling Research

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique