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Merck
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Key Documents

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Safety Information

T2909

Sigma-Aldrich

Tomatidine hydrochloride

≥85%

Synonym(s):

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

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CN¥6,317.12

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About This Item

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

CN¥6,317.12

Please contact Customer Service for Availability
Request a Bulk Order

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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concentration

500 ng/μL in TE buffer; DNA (10μg of plasmid DNA)

concentration

500 ng/μL in TE buffer; DNA (10μg of plasmid DNA)

concentration

500 ng/μL in TE buffer; DNA (10μg of plasmid DNA)

concentration

500 ng/μL in TE buffer; DNA (10μg of plasmid DNA)

product line

MISSION®

product line

MISSION®

product line

MISSION®

product line

MISSION®

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

General description

Tomatidine is a glycoalkaloid and an aglycone metabolite of tomatine present in high levels in unripe tomato.[1]

Application

Tomatidine hydrochloride has been used:
  • to evaluate its effect on nasopharyngeal carcinoma using cell proliferation and flow cytometry assay[2]
  • as a negative control in the non-specific inhibition on hedgehog signaling in hepatocellular carcinoma cell lines[3]
  • as a control for cell growth assay and expression studies in pancreatic cancer cells[4]

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.[1] 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.[5]

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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    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
    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)
    Activation of the hedgehog pathway in human hepatocellular carcinomas
    Huang S, et al.
    Carcinogenesis, 27(7), 1334-1340 (2006)
    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)
    View All Related Papers

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