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Merck
CN

T2909

Tomatidine hydrochloride

≥85%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H45NO2 · HCl
CAS Number:
6192-62-7
Molecular Weight:
452.11
UNSPSC Code:
41116107
NACRES:
NA.77
PubChem Substance ID:
24900092
MDL number:
MFCD00133866
Beilstein/REAXYS Number:
3920740

Key Documents

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Product Name

Tomatidine hydrochloride, ≥85%

InChI key

SXXHVPYRDFJKPG-XRWUXUKGSA-N

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

assay

≥85%

storage temp.

2-8°C

Quality Level

100

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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.

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

涉药品监管产品
涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
WXBF3421V
WXBD7975V
WXBD6489V
WXBD5555V
WXBD2504V

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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)
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
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)
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