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Key Documents

SML4104

Tomatine

new

≥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:
Molecular Weight:
1034.19
UNSPSC Code:
12352200
Pricing and availability is not currently available.

biological source

tomato

Quality Level

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

-10 to -25°C

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

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

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


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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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