T2909

Tomatidine hydrochloride

≥85%

• Synonyme(s) : 3β-Hydroxy-5α-tomatidane hydrochloride, 5α-Tomatidan-3β-ol hydrochloride
• Formule empirique (notation de Hill): C₂₇H₄₅NO₂ · HCl
• Numéro CAS: 6192-62-7
• Poids moléculaire : 452.11
• Numéro Beilstein : 3920740
• Numéro MDL: MFCD00133866
• Code UNSPSC : 41116107
• ID de substance PubChem : 24900092
• Nomenclature NACRES : NA.77

Propriétés

• Pureté: ≥85%
• Température de stockage: 2-8°C
• Chaîne SMILES: Cl[H].[H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])C[C@]5([H])O[C@]6(CC[C@H](C)CN6)[C@@H](C)[C@]45[H])[C@@]1(C)CC[C@H](O)C2
• InChI: 1S/C27H45NO2.ClH/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4;/h16-24,28-29H,5-15H2,1-4H3;1H/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27+;/m0./s1
• Clé InChI: SXXHVPYRDFJKPG-XRWUXUKGSA-N

Description

Description générale

Tomatidine is a glycoalkaloid and an aglycone metabolite of tomatine present in high levels in unripe tomato.

Application

Tomatidine hydrochloride has been used:

• to evaluate its effect on nasopharyngeal carcinoma using cell proliferation and flow cytometry assay
• as a negative control in the non-specific inhibition on hedgehog signaling in hepatocellular carcinoma cell lines
• as a control for cell growth assay and expression studies in pancreatic cancer cells

Actions biochimiques/physiologiques

Potent inhibitor of Staphylococcus aureus small-colony variants typically seen as complications of cystic fibrosis, with little or no effect on normal S. aureus strains. Also shows antiinflammatory activity by indirectly inhibiting iNOS and COX-2 pathways.

Tomatidine induces the anti-oxidant nuclear factor E2-related factor 2 (Nrf2) and mitophagy, favoring the delay in aging process in C.elegans. It is an inhibitor of muscle atrophy and promotes anabolism in muscle by activating mammalian target of rapamycin complex 1 (mTORC1). It may be useful for treating skeletal muscle atrophy.

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H302
• Conseils de prudence: P264 - P270 - P301 + P312 - P501
• Classification des risques: Acute Tox. 4 Oral
• 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
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)