beta-D-Galactopyranosid, (3 beta,5 alpha, 22 beta, 25S)-spirosolan-3-yl-O-beta-D-glucopyranosyl-(1=> 2)-O-(beta-D-xylopyranosyl-(1=> 3))-O-beta-D-glucopyranosyl-(1=> 4)-
Tomatine [for Cholesterol assay]
Grundinformationen
- CAS
17406-45-0- Standard-SMILES
CC1CCC2(NC1)OC1CC3C4CCC5CC(OC6OC(CO)C(OC7OC(CO)C(O)C(OC8OCC(O)C(O)C8O)C7OC7OC(CO)C(O)C(O)C7O)C(O)C6O)CCC5(C)C4CCC3(C)C1C2C- InChIKey
REJLGAUYTKNVJM-UHFFFAOYSA-N- Summenformel
- C50H83NO21
- Durchschnittliche Molmasse
- 1.034,2 g/mol
- Monoisotopische Masse
- 1.033,54575868
Überblick
tomatin (unspec. stereochem.) has been reported in Solanum kieseritzkii, Solanum dulcamara, and Solanum lycopersicum with data available.
Namen und Bezeichner
- Bevorzugter Name
- Tomatine [for Cholesterol assay]
- IUPAC
- 2-[2-[4,5-dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl)oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
- Lokaler Name
- beta-D-Galactopyranosid, (3 beta,5 alpha, 22 beta, 25S)-spirosolan-3-yl-O-beta-D-glucopyranosyl-(1=> 2)-O-(beta-D-xylopyranosyl-(1=> 3))-O-beta-D-glucopyranosyl-(1=> 4)-
- Englischer Name
- TOMATINE
- Summenformel
- C50H83NO21
- Molmasse
- 1034.19
Namen und Synonyme
Tomatine [for Cholesterol assay]a-tomatine.alpha.-TomatineC50H83NO21NSC9223alpha -tomatines9444.beta.-D-Galactopyranoside,5.alpha.,22.beta.,25S)-spirosolan-3-yl O-.beta.-D-glucopyranosyl-(1.fwdarw.2)-O-[.beta.-D-xylopyranosyl-(1.fwdarw.3)]-O-.beta.-D-glucopyranosyl-(1.fwdarw.4)-Tomatine [M+H]+SCHEMBL23567817NSC234440DB-050122
Weitere Namen anzeigen
alpha-tomatineTOMATINomatineTomatieTOMATINENSC 9223NSC 234440LYOCPERSICIN
(3-b,5a,22b25S)-Spirosolan-3-yl O-b-D-glucopyranosyl-1(1-2)-O-[b-D-xylopyranosyl-(1-3)]-O-b-D-glucopyranosyl-(1-4)-b-D-galactopyranoside|A-D-Galactopyranoside, (3|A,5|A,22|A,25S)-spirosolan-3-yl O-|A-D-glucopyranosyl-(1 inverted exclamation marku2)-O-[|A-D-xylopyranosyl-(1 inverted exclamation marku3)]-O-|A-D-glucopyranosyl-(1 inverted exclamation marku4)-2-[2-[4,5-dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl)oxy-tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxytetrahydropyran-2-yl)oxy-tetrahydropyran-3-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,7
- Polarare Oberfläche (TPSA)
- 338 Ų
- H-Brücken-Donoren
- 13
- H-Brücken-Akzeptoren
- 22
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 72
- Formalladung
- 0
- Komplexität
- 1.840
Experimentelle und physikochemische Eigenschaften
Melting Point263 - 267 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 300 · 300-305°C
- Siedepunkt
- 806.69 °C · 806.69°C (rough estimate)
- Dichte
- 1.48 · 1.48±0.1 g/cm3 (20 ºC 760 Torr)
- Brechungsindex
- 1.528 · 1.5280 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly)
- Aggregatzustand
- Solid
- pka
- 12.77 · 12.77±0.70(Predicted)
- Farbe
- White to Off-White
- Merck
- 14 · 14,9545
- InChIKey
- REJLGAUYTKNVJM-GXOLHJPNNA-N
- LogP
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- ridadr
- 1544
- hs_code
- 29329990
- RTECS-Nr.
- XW1050000
- risk_code
- 23/25-22
- Toxizität
- LD orally in rats: 900-1000 mg/kg (Wilson)
- hazard_code
- Xn
- safety_code
- 45-24/25-22
- Giftige Stoffe Daten
- 17406-45-0(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsCytoplasm
Anwendungen
BeschreibungThis glycosidic alkaloid has been obtained from the dried leaves of Lycopersicum pimpinelli/olium (Syn. Solanum racemigerum) and also occurs in L. esculentum; L. hirsutum; L. peruvianum; L. peruvianum var. chutatum and L. putatum. The alkaloid forms colourless needles from MeOH and has a somewhat indefinite melting point about 270°C. It is laevorotatory with [α]20D - 30° (pyridine) and on hydrolysis with H2S04 yields tomatidine, I mole of galactose, 2 moles of glucose and 1 mole of xylose. The tetrasaccharide unit is known as lycotetraose. Partial hydrolysis with acid yields a series of products depending upon which, and how many, of the sugar residues are split off from the molecule. Those which have been isolated are: tomatidine lycotriose I (galactose-glucose-glucose); tomatidine lycotriose II (galactose-glucose-xylose); tomatidine lycobiose (galactose-glucose) and tomatidine-galactose.
VerwendenTomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.
Vor- und nachgelagerte Produkte
Nachgelagerte Produkte
Ergänzende Hinweise
DefinitionChEBI: A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galac ose.
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