Tomatidine (hydrochloride)

Tomatidine is a steroidal alkaloid that has been found in the skins and leaves of tomatoes. It suppresses NF-kappaB signaling in LPS-stimulated macrophages, blocking induced expression of inducible nitric oxide synthase (iNOS) and COX-2. Tomatidine inhibits acid sphingomyelinase activity by 84.2% when used at a concentration of 10 mM. It also has antibacterial properties, preferentially blocking the replication of S. aureus variants that are pathogenic in cystic fibrosis over normal strains (MICs = 0.12 and >16 µg/ml, respectively). It prevents skeletal muscle atrophy associated with fasting or spinal cord injury in mice. Tomatidine has also been used as a negative control for cyclopamine (Cay-11321) in studies involving signaling mediated by the hedgehog pathway.Formal Name: (3beta,5alpha,22beta,25S)-spirosolan-3-ol, monohydrochloride. CAS Number: 6192-62-7. Molecular Formula: C27H45NO2 . HCl. Formula Weight: 452.1. Purity: >90%. Formulation: (Request formulation change), A crystalline solid. Solubility: Methanol: 10 mg/ml. SMILES: C[C@@H](CC1)CN[C@@]21O[C@@]3([H])C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3([H])[C@@H]2C.Cl. InChi Code: 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-VXJLCZPPSA-N.