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Safety Information

T2909

Sigma-Aldrich

Tomatidine hydrochloride

≥85%

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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
PubChem Substance ID:
24900092
NACRES:
NA.77

Quality Level

100

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

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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.

Pictograms

Exclamation mark
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

Regulatory Information

监管及禁止进口产品

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Systems-based discovery of tomatidine as a natural small molecule inhibitor of skeletal muscle atrophy
Dyle MC, et al.
Test, 289(21), 14913-14924 (2014)
Jessica L Cooperstone et al.
Scientific reports, 7(1), 5106-5106 (2017-07-13)
Prolonged tomato consumption can mitigate ultraviolet (UV) light induced sunburn via unknown mechanisms. Dietary carotenoids distributed to skin are hypothesized to protect skin against UV-induced damage, although other phytochemicals may play a role. We hypothesize that tomato consumption would protect
Maxime Lamontagne Boulet et al.
Antimicrobial agents and chemotherapy, 62(6) (2018-04-04)
Methicillin-resistant Staphylococcus aureus (MRSA) is a leading cause of deadly hospital-acquired infections. The discovery of anti-Staphylococcus antibiotics and new classes of drugs not susceptible to the mechanisms of resistance shared among bacteria is imperative. We recently showed that tomatidine (TO)
Tomatidine enhances lifespan and healthspan in C. elegans through mitophagy induction via the SKN-1/Nrf2 pathway
Fang EF, et al.
Scientific reports, 7, 46208-46208 (2017)
Expression and regulation of hedgehog signaling pathway in pancreatic cancer
Yang Y, et al.
Langenbeck'S Archives of Surgery / Deutsche Gesellschaft Fur Chirurgie, 395(5), 515-525 (2010)
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