Basic information
- 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- Molecular formula
- C50H83NO21
- Average molar mass
- 1,034.2 g/mol
- Monoisotopic mass
- 1,033.54575866
Overview
tomatin (unspec. stereochem.) has been reported in Solanum kieseritzkii, Solanum dulcamara, and Solanum lycopersicum with data available.
Names & identifiers
- Preferred 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
- English name
- TOMATINE
- Molecular formula
- C50H83NO21
- Molecular weight
- 1034.19
Names & synonyms
Tomatine [for Cholesterol assay].alpha.-TomatineC50H83NO21NSC9223alpha -tomatine.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]+SCHEMBL23567817beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-NSC234440DB-050122(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
Show more names
alpha-tomatineTOMATINomatineTomatieTOMATINENSC 9223a-TomatineNSC 234440LYOCPERSICIN
|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
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 338 Ų
- Hydrogen bond donors
- 13
- Hydrogen bond acceptors
- 22
- Rotatable bonds
- 11
- Heavy atoms
- 72
- Formal charge
- 0
- Complexity
- 1,840
Experimental & physicochemical properties
Melting Point263 - 267 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 300 · 300-305°C
- alpha
- 20 · D20 -18° (c = 0.55 in pyridine)
- Boiling point
- 806.69 °C · 806.69°C (rough estimate)
- Density
- 1.48 · 1.48±0.1 g/cm3 (20 ºC 760 Torr)
- refractive index
- 1.528 · 1.5280 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly)
- form
- Solid
- pka
- 12.77 · 12.77±0.70(Predicted)
- color
- White to Off-White
- Merck
- 14 · 14,9545
- InChIKey
- REJLGAUYTKNVJM-GXOLHJPNNA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- rtecs
- XW1050000
- ridadr
- 1544
- hs_code
- 29329990
- Toxicity
- LD orally in rats: 900-1000 mg/kg (Wilson)
- risk_code
- 23/25-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 45-24/25-22
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
- Hazardous Substances Data
- 17406-45-0(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionThis 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.
UsesTomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.
UsesPrecipitating agent for steroids.
Upstream & downstream products
Downstream products
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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