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Merck
CN

SML4104

Tomatine

≥95% (HPLC)

Synonym(s):

(3β,5α,22β,25S)-Spirosolan-3-yl O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside, Lycopersicin, NSC 234440, NSC 9223, Spirosolane, α-Tomatine, alpha-tomatine

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About This Item

Empirical Formula (Hill Notation):
C50H83NO21
CAS Number:
17406-45-0
Molecular Weight:
1034.19
NACRES:
NA.21
Assay:
≥95% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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SMILES string

N1[C@]2(O[C@@H]3[C@@H]([C@@]4([C@H]([C@H]5[C@@H]([C@@]6([C@H](C[C@H](CC6)O[C@@H]7O[C@@H]([C@@H]([C@@H]([C@H]7O)O)O[C@@H]8O[C@@H]([C@H]([C@@H]([C@H]8O[C@@H]%10O[C@@H]([C@H]([C@@H]([C@H]%10O)O)O)CO)O[C@@H]9OC[C@H]([C@@H]([C@H]9O)O)O)O)CO)CO)CC5)C)CC4)C3)C)[, C[C@@H]1[C@@]2(O[C@]3([H])[C@@]1([H])[C@]4(CC[C@]5([H])[C@@]6([C@@](C[C@@H](O[C@@H]7O[C@@H]([C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O[C@@H]9OC[C@@H](O)[C@H](O)[C@H]9O)[C@H]8O[C@H]%10[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O%10)[C@@H]([C@H]7O)O)CO)CC6)([H])CC[C@

InChI key

REJLGAUYTKNVJM-SGXCCWNXSA-N

biological source

tomato

assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

-10 to -25°C

Quality Level

100

Biochem/physiol Actions

Phytochemical from tomatoes; protects the plant from microbes; induces apoptosis in cancer cell lines.
Tomatine (Lycopersicin) is a natural glycoalkaloid from tomatoes that exhibits fungicidal, antimicrobial, and insecticidal properties. Tomatine induces apoptosis in cancer cell lines.

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

Regulatory Information

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

Lot/Batch Number
0000404660
0000387244
0000387244
0000404660

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Cesar Echeverría et al.
Frontiers in pharmacology, 13, 1003264-1003264 (2022-09-27)
Background: There is abundant ethnopharmacological evidence the uses of regarding Solanum species as antitumor and anticancer agents. Glycoalkaloids are among the molecules with antiproliferative activity reported in these species. Purpose: To evaluate the anticancer effect of the Solanum glycoalkaloid tomatine
Shin-Ichi Ito et al.
FEBS letters, 581(17), 3217-3222 (2007-06-26)
The tomato saponin alpha-tomatine has been proposed to kill sensitive cells by binding to cell membranes followed by leakage of cell components. However, details of the modes of action of the compound on fungal cells are poorly understood. In the

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