Anisatin
Basic information
- CAS
5230-87-5- Standard SMILES
C[C@@H]1C[C@@H](O)[C@@]2(O)[C@@]13C[C@@H](OC(=O)[C@@H]3O)[C@](C)(O)[C@@]21COC1=O- InChIKey
GEVWHIDSUOMVRI-QWNPAUMXSA-N- Molecular formula
- C15H20O8
- Average molar mass
- 328.31 g/mol
- Monoisotopic mass
- 328.11581759
Overview
(−)-anisatin has been reported in Illicium simonsii, Illicium majus, and other organisms with data available.
Names & identifiers
- Preferred name
- Anisatin
- IUPAC
- (1S,2R,4R,5R,6S,7R,8R,11R)-4,5,7,11-tetrahydroxy-2,7-dimethylspiro[9-oxatricyclo[6.3.1.01,5]dodecane-6,3'-oxetane]-2',10-dione
- English name
- ANISATIN
- Molecular formula
- C15H20O8
- Molecular weight
- 328.31
Names & synonyms
AnisatinW9K8802FZLDTXSID6058396(1S,2R,4R,5R,6S,7R,8R,11R)-4,5,7,11-tetrahydroxy-2,7-dimethylspiro[9-oxatricyclo[6.3.1.01,5]dodecane-6,3'-oxetane]-2',10-dione(1S,2R,4R,5R,6S,7R,8R,11R)-4,5,7,11-tetrahydroxy-2,7-dimethylspiro(9-oxatricyclo(6.3.1.01,5)dodecane-6,3'-oxetane)-2',10-dioneRefChem:558132DTXCID70321354',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro(oxetane-3,6'-tricyclo(6.3.1.01,5)dodecane)-4,10'-dione5230-87-5aniasatin(-)-AnisatinUNII-W9K8802FZL
Show more names
ANISATIN(RG)Fruit of illicium anisatum L.(1R,6S)-4,5,6a,7,8,9-Hexahydro-1,5α,6aα,7α-tetrahydroxy-5,9β-dimethylspiro[6H-4α,9aα-methanocyclopenta[d]oxocin-6,3'-oxetane]-2,2'(1H)-dione(1R,6S)-4,5,6a,7,8,9,9a-Heptahydro-1,5α,6aα,7α-tetrahydroxy-5,9β-dimethylspiro[6H-4α,9aα-methanocyclopenta[d]oxocin-6,3'-oxetane]-2,2'(1H)-dioneSpiro[4H-4,9a-methanocyclopent[d]oxocin-6(2H),3'-oxetane]-2,2'-dione, hexahydro-1,5,6a,7-tetrahydroxy-5,9-dimethyl-, (1R,3'S,4R,5R,6aR,7R,9R,9aS)-
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 134 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 0
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 621
Physicochemical properties
- Melting point
- 227 · 227-228℃
- Boiling point
- 609.5 · 609.5±55.0 °C(Predicted)
- Density
- 1.63 · 1.63±0.1 g/cm3 (20 ºC 760 Torr)
- storage temp.
- -20 °C · -20°C
- pka
- 12.01 · 12.01±0.70(Predicted)
- form
- Solid
- color
- White to off-white
- Major Application
- food and beverages
- InChI
- 1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8-,9+,12+,13+,14+,15-/m1/s1
- InChIKey
- GEVWHIDSUOMVRI-QWNPAUMXSA-N
- SMILES
- O1[C@H]2[C@@]([C@]3([C@@]4([C@@]([C@@H](C[C@H]4O)C)([C@H](C1=O)O)C2)O)COC3=O)(O)C
- LogP
- -0.93 · -0.930 (est)
- FDA UNII
- 9 K8802FZL · W9K8802FZL
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300+H330 (97.5%): Fatal if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]
P260, P264, P270, P271, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Not Classified
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Toxicology
Health EffectsDeath may result from respiratory paralysis. (L1226)
Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)
Toxicity SummaryAnisatin acts as a GABA system antagonist. It binds non-competitively to the picrotoxinin site of the GABA receptor, prolonging the closed time of the receptor channel and reducing the probability of it opening. (A345)
Signs and SymptomsSymptoms of anisatin poisoning include diarrhea, vomiting, and stomach pain, followed by nervous system excitation, seizures, loss of consciousness. (L1226)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
Chemistry & industry
Uses & manufacturing
UsesAnisatin is a plant toxin found in the Japanese star anise (Illicium anisatum). The Japanese star anise has been burned as incense in Japan, where it is known as shikimi, as well as used in topical folk remedies. (L1226)
Applications
Usesfood and beverages
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Related reactions
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Compound notes
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