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Tomatine information


α-tomatine
Names
IUPAC name
(22S,25S)-5α-spirosolan-3β-yl β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside [1]
Other names
Tomatine, Tomatin, Lycopersicin
Identifiers
CAS Number
  • 17406-45-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:9630 checkY
ChEMBL
  • ChEMBL525778 checkY
ChemSpider
  • 26536 checkY
ECHA InfoCard 100.037.647 Edit this at Wikidata
PubChem CID
  • 28523
UNII
  • 31U6547O08 checkY
CompTox Dashboard (EPA)
  • DTXSID5040413 Edit this at Wikidata
InChI
  • InChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1 checkY
    Key: REJLGAUYTKNVJM-SGXCCWNXSA-N checkY
SMILES
  • C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)NC1
Properties
Chemical formula
C50H83NO21 [2]
Molar mass 1034.18816 [3]
Appearance crystalline solid
Melting point 263-268 °C [4]
Solubility in water
insoluble but soluble in methanol, ethanol, dioxane and propylene glycol[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Tomatine (sometimes called tomatin or lycopersicin) is a glycoalkaloid, found in the stems and leaves of tomato plants, and in the fruits at much lower concentrations. Chemically pure tomatine is a white crystalline solid at standard temperature and pressure.[1][5]

Tomatine is sometimes confused with the glycoalkaloid solanine.[6]

  1. ^ a b EBI Web Team. "tomatine (CHEBI:9630)".
  2. ^ 1.http://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+17406-45-0
  3. ^ US Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8212
  4. ^ a b The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 1228
  5. ^ Degtyarenko, K.; De Matos, P.; Ennis, M.; Hastings, J.; Zbinden, M.; McNaught, A.; Alcantara, R.; Darsow, M.; Guedj, M.; Ashburner, M. (2007). "ChEBI: A database and ontology for chemical entities of biological interest". Nucleic Acids Research. 36 (Database issue): D344–50. doi:10.1093/nar/gkm791. PMC 2238832. PMID 17932057.
  6. ^ Cite error: The named reference McGee was invoked but never defined (see the help page).

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