Tomatidine

Tomatidine is a natural compound found in leaves of tomatoes and green tomatoes.^[1] Chemically, it is the aglycone of tomatine. It has been shown to have potential health benefits in animal models.^[2] For instance, tomatidine inhibited skeletal muscle atrophy in a mouse model of skeletal unloading-induced atrophy^[3] and to prevent or reverse sarcopenia (loss of muscle mass and strength due to biological aging) by inhibiting the activation of genes by ATF4.^[4]

Quick facts Names, Identifiers ...

Tomatidine

Names
IUPAC name (1R,2S,4S,5′S,6S,7S,8R,9S,12S,13S,16S,18S)-5′,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2′-piperidine]-16-ol
Other names 5alpha-Tomatidan-3beta-ol (3beta,5alpha,22beta,25S)-Spirosolan-3-ol Tomatidin (22S,25S)-5alpha-spirosolan-3beta-ol
Identifiers
CAS Number	77-59-8 6192-62-7
3D model (JSmol)	Interactive image
Beilstein Reference	91747
ChEBI	CHEBI:9629
ChEMBL	ChEMBL2165711
ChemSpider	59019
ECHA InfoCard	100.000.947
EC Number	201-040-3
KEGG	C10826
PubChem CID	65576
UNII	2B73S48786
CompTox Dashboard (EPA)	DTXSID0037102
InChI InChI=1S/C27H45NO2/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/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-/m0/s1 Key: XYNPYHXGMWJBLV-VXPJTDKGSA-N
SMILES CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)NC1
Properties
Chemical formula	C27H45NO2
Molar mass	415.662 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H331
Precautionary statements	P261, P264, P270, P271, P301+P310, P301+P312, P304+P340, P311, P321, P330, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Dietary supplementation with ~0.04% tomatidine for 10 weeks reduced plasma cholesterol and atherosclerosis in ApoE-deficient mice without evidence of toxicity.^[5]