(+)-aspidospermidine
 
Notes:
None found
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CAS Number: 2912-09-6Picture of molecule3D/inchi
Nikkaji Web: J39.325H
XlogP3-AA: 4.00 (est)
Molecular Weight: 282.43022000
Formula: C19 H26 N2
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 34.05 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
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Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for (+)-aspidospermidine usage levels up to:
 not for fragrance use.
 
Recommendation for (+)-aspidospermidine flavor usage levels up to:
 not for flavor use.
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Safety References:
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 6857472
National Institute of Allergy and Infectious Diseases: Data
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References:
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 6857472
Pubchem (cas): 2912-09-6
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
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(IUPAC): Periodic Table of the Elements
CHEBI: View
HMDB (The Human Metabolome Database): HMDB30360
FooDB: FDB002206
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 aspidosperma quebracho-blanco
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Synonyms:
(+)-aspidospermidine
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Articles:
PubMed: Directed Fischer Indolization as an Approach to the Total Syntheses of (+)-Aspidospermidine and (-)-Tabersonine.
PubMed: Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization.
PubMed: Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution.
PubMed: Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (-)-Quebrachamine, (+)-Aspidospermidine, (-)-Aspidospermine, (-)-Pyrifolidine, and Related Natural Products.
PubMed: Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine.
PubMed: Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (-)-Goniomitine, (+)-Aspidospermidine, and (-)-Quebrachamine.
PubMed: Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine.
PubMed: Preparation of the Core Structure of Aspidosperma and Strychnos Alkaloids from Aryl Azides by a Cascade Radical Cyclization.
PubMed: Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine.
PubMed: Concise total synthesis of (±)-aspidospermidine.
PubMed: Unified strategy to monoterpene indole alkaloids: total syntheses of (±)-goniomitine, (±)-1,2-dehydroaspidospermidine, (±)-aspidospermidine, (±)-vincadifformine, and (±)-kopsihainanine A.
PubMed: Pd(II)-catalyzed one-step construction of cycloalkane-fused indoles and its application in formal synthesis of (±)-aspidospermidine.
PubMed: Domino Michael/Mannich/N-alkylation route to the tetrahydrocarbazole framework of aspidosperma alkaloids: concise total syntheses of (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine.
PubMed: Enantioselective palladium-catalyzed decarboxylative allylation of carbazolones: total synthesis of (-)-aspidospermidine and (+)-kopsihainanine A.
PubMed: Regioselective inter- and intramolecular formal [4+2] cycloaddition of cyclobutanones with indoles and total synthesis of (±)-aspidospermidine.
PubMed: Chemical synthesis of Aspidosperma alkaloids inspired by the reverse of the biosynthesis of the rhazinilam family of natural products.
PubMed: Pd(II)-catalyzed regioselective 2-alkylation of indoles via a norbornene-mediated C-H activation: mechanism and applications.
PubMed: Indole alkaloids synthesis via a selective cyclization of aminocyclopropanes.
PubMed: Cyclopropanes and hypervalent iodine reagents: high energy compounds for applications in synthesis and catalysis.
PubMed: Synthetic studies on amaryllidaceae and other terrestrially derived alkaloids.
PubMed: Collective synthesis of natural products by means of organocascade catalysis.
PubMed: Catalytic selective cyclizations of aminocyclopropanes: formal synthesis of aspidospermidine and total synthesis of goniomitine.
PubMed: Evidence for a role of 5-HT(1A) receptor on antinociceptive action from Geissospermum vellosii.
PubMed: Concise total synthesis of (+/-)-aspidospermidine via an oxidative Hosomi-Sakurai process.
PubMed: Asymmetric construction of quaternary carbon centers by sequential conjugate addition of lithium amide and in situ alkylation: utility in the synthesis of (-)-aspidospermidine.
PubMed: Stereoselective formation of fused tricyclic amines from acyclic aldehydes by a cascade process involving condensation, cyclization, and dipolar cycloaddition.
PubMed: Domino double Michael-Claisen cyclizations: a powerful general tool for introducing quaternary stereocenters at C4 of cyclohexane-1,3-diones and total synthesis of diverse families of sterically congested alkaloids.
PubMed: Highly efficient synthesis of tricyclic amines by a cyclization/cycloaddition cascade: total syntheses of aspidospermine, aspidospermidine, and quebrachamine.
PubMed: Formal synthesis of aspidosperma alkaloids via the intramolecular [3 + 2] cycloaddition of 2-azapentdienyllithiums.
PubMed: A short total synthesis of (+/-)-aspidospermidine.
PubMed: Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.
PubMed: A study of vinyl radical cyclization using N-alkenyl-7-bromo-substituted hexahydroindolinones.
PubMed: Exploiting the palladium[0]-catalysed Ullmann cross-coupling reaction in natural products chemistry: application to a total synthesis of the alkaloid (+/-)-aspidospermidine.
PubMed: Total synthesis of (+)-aspidospermidine: a new strategy for the enantiospecific synthesis of aspidosperma alkaloids.
PubMed: Antiplasmodial activity of aspidosperma indole alkaloids.
PubMed: An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.
PubMed: Tandem radical cyclizations with iodoaryl azides: formal total synthesis of (+/-)-aspidospermidine.
PubMed: Regiocontrol in an intramolecular Schmidt reaction: total synthesis of (+)-aspidospermidine.
PubMed: Novel [1,5] sigmatropic rearrangements of cyclohexadienones generated from Fischer carbene complexes. A new strategy for installing the C-20 angular ethyl group in Aspidospermidine alkaloids.
PubMed: Total synthesis of (+/-)-aspidospermidine.
PubMed: Synthetic Applications of 2-(1,3-Dithian-2-yl)indoles. 7. Synthesis of Aspidospermidine.
PubMed: Alkaloids from Aspidosperma species from Bolivia.
PubMed: Total synthesis of indole and dihydroindole alkaloids. V. The total synthesis of dl-quebrachamine and dl-aspidospermidine. A general entry into the aspidosperma alkaloids.
PubMed: Cyclization in the cleavamine series: x-ray analysis of N(a)-acetyl-7-ethyl-5-desethyl-aspidospermidine N(b)-methiodide.
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