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T2909

Sigma-Aldrich

Tomatidine hydrochloride

≥85%

Synonyme(s) :

3β-Hydroxy-5α-tomatidane hydrochloride, 5α-Tomatidan-3β-ol hydrochloride

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About This Item

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

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

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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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

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)

Certificats d'analyse (COA)

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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)
Shuhong Huang et al.
Carcinogenesis, 27(7), 1334-1340 (2006-02-28)
Liver cancers, the majority of which are hepatocellular carcinomas (HCCs), rank as the fourth in cancer mortality worldwide and are the most rapidly increasing type of cancer in the United States. However, the molecular mechanisms underlying HCC development are not
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)
Activation of the hedgehog pathway in human hepatocellular carcinomas
Huang S, et al.
Carcinogenesis, 27(7), 1334-1340 (2006)
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
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