Tutin
Grundinformationen
- CAS
2571-22-4- Standard-SMILES
C=C(C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)[C@H]3O[C@H]3[C@]3(CO3)[C@]1(C)[C@@H]2O- InChIKey
CCAZWUJBLXKBAY-ULZPOIKGSA-N- Summenformel
- C15H18O6
- Durchschnittliche Molmasse
- 294,3 g/mol
- Monoisotopische Masse
- 294,11033829
Überblick
Tutin is a gamma-lactone.
Namen und Bezeichner
- Bevorzugter Name
- Tutin
- IUPAC
- (1S,2R,3S,5R,6R,7R,8S,9R,12R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one
- Englischer Name
- TUTIN
- Summenformel
- C15H18O6
- Molmasse
- 294.3
Namen und Synonyme
TutinTutineTutuToot poison2571-22-4(+)-TutinDTXSID30180400B69P754702(1S,2R,3S,5R,6R,7R,8S,9R,12R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one(1S,2R,3S,5R,6R,7R,8S,9R,12R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro(4,10-dioxatetracyclo(7.2.1.02,7.03,5)dodecane-6,2'-oxirane)-11-oneRefChem:192599DTXCID00102891
Weitere Namen anzeigen
Tutin solutionTutin, 20 μg/g acetonitrile solution(7R,8R)-1aβ,1b,5,6,6a,7aβ-Hexahydro-1bα,6β-dihydroxy-6aα-methyl-8-(1-methylethenyl)spiro[2α,5α-methano-7H-oxireno[3,4]cyclopent[1,2-d]oxepine-7,2'-oxiran]-3(2H)-oneSpiro[2,5-methano-7H-oxireno[3,4]cyclopent[1,2-d]oxepin-7,2'-oxiran]-3(2H)-one, hexahydro-1b,6-dihydroxy-6a-methyl-8-(1-methylethenyl)-, (1aS,1bR,2S,2'R,5R,6S,6aR,7aR,8R)-Spiro(2,5-methano-7H-oxireno(3,4)cyclopent(1,2-D)oxepin-7,2'-oxiran)-3(2ah)-one, 1A-beta,1B,5A,6,6A,7A-beta-hexahydro-1B-alpha,6-beta-dihydroxy-8A-isopropenyl-6A-alpha-methyl-
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,5
- Polarare Oberfläche (TPSA)
- 91,8 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 603
Experimentelle und physikochemische Eigenschaften
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
Physikochemische Eigenschaften
- Schmelzpunkt
- 209 · 209-212°; mp 204-205° (Wakamatsu)
- Siedepunkt
- 356.07 °C · 356.07°C (rough estimate)
- Dichte
- 1.1975 · 1.1975 (rough estimate)
- Brechungsindex
- 1.4359 · 1.4359 (estimate)
- storage temp.
- -20 °C · -20°C
- pka
- 12.83 · 12.83±0.70(Predicted)
- Major Application
- cleaning productscosmeticsfood and beveragespersonal care
- InChI
- 1S/C15H18O6/c1-5(2)6-7-12(17)20-8(6)9(16)13(3)14(4-19-14)10-11(21-10)15(7,13)18/h6-11,16,18H,1,4H2,2-3H3/t6-,7+,8+,9+,10+,11-,13-,14+,15-/m0/s1
- InChIKey
- CCAZWUJBLXKBAY-ULZPOIKGSA-N
- SMILES
- O1[C@@]2([C@@H]3O[C@@H]3[C@@]4([C@]2([C@@H]([C@@H]5OC(=O)[C@H]4[C@@H]5C(=C)C)O)C)O)C1
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxikologische Informationen
Health EffectsTutin has powerful convulsant effects. (L1250)
Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)
Toxicity SummaryTutin is a potent antagonist of the glycine receptor. (L1250)
Signs and SymptomsTutin has powerful convulsant effects. (L1250)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Sicherheitsdaten
- wgk
- WGK 2
- Toxizität
- LD50 i.p. in female mice: 3.0 mg/kg (Jarboe)
- Speicherklasse
- 3 - Flammable liquids
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Chemie und Industrie
Verwendung und Herstellung
UsesTutin is a plant toxin found in the tutu plant (genus Coriaria). (L1250)
Anwendungen
VerwendenCoriaria Lactone can be used in biological study for effects of tutin and its derivatives on GAD and GABA-T in Pseudelatia separata tested as novel active ingredients for pest control. It is also utilized in agricultural use for anti-feedant activities and effects of tutin and its derivatives on mythimna separata and its physiological parameters.
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