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Basic information
- 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- Molecular formula
- C15H18O6
- Average molar mass
- 294.303 g/mol
- Monoisotopic mass
- 294.1103383
Names & identifiers
- Preferred name
- (+)-Tutin
- IUPAC
- (1aS,1bR,2S,2'R,5R,6S,6aR,7aR,8R)-1b,6-Dihydroxy-6a-methyl-8-(prop-1-en-2-yl)hexahydrospiro[2,5-methanooxireno[3,4]cyclopenta[1,2-d]oxepine-7,2'-oxiran]-3(2H)-one
- English name
- TUTIN
- Molecular formula
- C15H18O6
- Molecular weight
- 294.3
Names & synonyms
TutuTUTINTutineToot poisonTutin 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-(1As-(1aalpha,1bbeta,2beta,5beta,6alpha,6abeta,7beta,7aalpha,8S*))-hexahydro-1B,6-dihydroxy-6A-methyl-8-(1-methylethenyl)spiro(2,5-methano-7H-oxireno(3,4)cyclopent(1,2-D)oxepin-7,2'-oxiran)-3(2alpha H)-one
Database identifiers
- CAS
2571-22-4- PubChem CID
- 75729
- DTXSID
DTXSID30180400- ChEMBL
CHEMBL2268727、CHEMBL297057
Properties
Physicochemical properties
- Melting point
- 209 · 209-212°; mp 204-205° (Wakamatsu)
- alpha
- 20 · D20 +9.25° (alc); D17 +13.9° (c = 0.75, methanol)
- Boiling point
- 356.07 °C · 356.07°C (rough estimate)
- Density
- 1.1975 · 1.1975 (rough estimate)
- refractive index
- 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
- LogP
- 1.38 · 1.380 (est)
- FDA UNII
- 69 P754702 · B69P754702
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501
- WGK Germany
- 2 · WGK 2
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
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
- wgk
- WGK 2
- Toxicity
- LD50 i.p. in female mice: 3.0 mg/kg (Jarboe)
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Applications
UsesCoriaria 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.
Additional notes
DefinitionChEBI: Tutin is a gamma-lactone.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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