T2909

Tomatidine hydrochloride

≥85%

• Synonym(s): 3β-Hydroxy-5α-tomatidane hydrochloride, 5α-Tomatidan-3β-ol hydrochloride
• Empirical Formula (Hill Notation): C₂₇H₄₅NO₂ · HCl
• CAS Number: 6192-62-7
• Molecular Weight: 452.11
• Beilstein: 3920740
• MDL number: MFCD00133866
• UNSPSC Code: 41116107
• PubChem Substance ID: 24900092
• NACRES: NA.77

Properties

• Assay: ≥85%
• storage temp.: 2-8°C
• SMILES string: 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
• InChI key: SXXHVPYRDFJKPG-XRWUXUKGSA-N

Description

General description

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

Biochem/physiol Actions

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves