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(+)-Cinchonine - 85%, high purity , CAS No.118-10-5

4 Citations COA COA
    Grade & Purity:
  • ≥85%
In stock
Item Number
C431523
Grouped product items
SKU Size
Availability
 Price Qty
C431523-25g
25g
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$39.90
C431523-100g
100g
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$99.90
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View related series
Anti-infection (2803) Apoptosis (4276) Autophagy (1917) Intrinsic Pathway (690) Ion channel (2197) Parasite (997)

Basic Description

Synonyms (S)-quinolin-4-yl((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol | GNF-Pf-3189 | NCGC00262542-03 | .alpha.-Quinidine | NSC 6176 | HMS2096J18 | Prestwick3_000608 | LA40221 | (8R,9S)-Cinchonine | UNII-V43X79NZCD | 2-Quinuclidinemethanol, .alpha.-4-quinolyl-5-v
Specifications & Purity ≥85%
Product Description

General Description

(+)-Cinchonine, one of the alkaloids found in the barks of cinchona tree, is mainly used in the treatment of malaria. It belongs to the monoclinic crystal system and P 2 1 space group. The solubility of cinchonine can be improved by the formation of inclusion complexes with cyclodextrins.


Application

(+)-Cinchonine, in the presence of lithium diisopropylamide (LDA) forms a complex, which can catalyze the asymmetric conjugate addition of benzyl- and alkylphosphonates to aromatic and heteroaromatic nitroalkenes to form the corresponding adducts.


Other Notes

remainder dihydrocinchonine

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Alkaloids and derivatives
Class Cinchona alkaloids
Subclass Not available
Intermediate Tree Nodes Not available
Direct Parent Cinchona alkaloids
Alternative Parents 4-quinolinemethanols  Quinuclidines  Aralkylamines  Pyridines and derivatives  Piperidines  Benzenoids  Heteroaromatic compounds  Trialkylamines  Secondary alcohols  1,2-aminoalcohols  Azacyclic compounds  Organopnictogen compounds  Hydrocarbon derivatives  Aromatic alcohols  
Molecular Framework Aromatic heteropolycyclic compounds
Substituents Cinchonan-skeleton - 4-quinolinemethanol - Quinoline - Quinuclidine - Aralkylamine - Piperidine - Pyridine - Benzenoid - Heteroaromatic compound - 1,2-aminoalcohol - Secondary alcohol - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Amine - Alcohol - Aromatic alcohol - Aromatic heteropolycyclic compound
Description This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.
External Descriptors cinchona alkaloid - (8xi)-cinchonan-9-ol

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLC2A1 Tchem Glucose transporter (14755 Activities)
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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
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A498 (42825 Activities)
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ACHN (49357 Activities)
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CAKI-1 (44928 Activities)
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COLO 205 (50209 Activities)
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DU-145 (51482 Activities)
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HL-60 (67320 Activities)
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HT-29 (80576 Activities)
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Huh-7 (12904 Activities)
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K562 (73714 Activities)
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KM12 (47707 Activities)
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M14 (47487 Activities)
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MCF7 (126967 Activities)
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MOLT-4 (49676 Activities)
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OVCAR-3 (48710 Activities)
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OVCAR-4 (44535 Activities)
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OVCAR-5 (45555 Activities)
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OVCAR-8 (47708 Activities)
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PC-3 (62116 Activities)
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RPMI-8226 (44974 Activities)
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RXF 393 (41971 Activities)
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SF-295 (48000 Activities)
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SK-MEL-2 (46422 Activities)
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SK-MEL-28 (48833 Activities)
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SK-MEL-5 (47095 Activities)
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SK-OV-3 (52876 Activities)
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SN12C (47755 Activities)
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SNB-19 (46794 Activities)
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TK-10 (45540 Activities)
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U-251 (51189 Activities)
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UACC-257 (46019 Activities)
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UACC-62 (47335 Activities)
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UO-31 (46270 Activities)
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WI-38 (2654 Activities)
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786-0 (47912 Activities)
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A549 (127892 Activities)
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NCI/ADR-RES (33767 Activities)
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T47D (39041 Activities)
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EKVX (44102 Activities)
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NCI-H322M (45589 Activities)
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HCT-116 (91556 Activities)
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Hs-578T (29457 Activities)
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HepG2 (196354 Activities)
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NCI-H460 (60772 Activities)
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SF-268 (49410 Activities)
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IGROV-1 (47897 Activities)
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LOX IMVI (44321 Activities)
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HOP-62 (47048 Activities)
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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
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Trypanosoma brucei brucei (13300 Activities)
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Plasmodium falciparum (966862 Activities)
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Trichomonas vaginalis (2376 Activities)
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ht1 Hexose transporter 1 (14071 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BCHE Cholinesterase (8742 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Leishmania mexicana mexicana (27 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SARS-CoV-2 (38078 Activities)
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Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
INCHI InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
InChIKey KMPWYEUPVWOPIM-QAMTZSDWSA-N
Smiles C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
Isomeric SMILES C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O
WGK Germany 3
RTECS GD3500000
Molecular Weight 294.39
Beilstein 89689
Reaxy-Rn 89687
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=89687&ln=

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Specific Rotation[α] 223 ° (C=0.5, EtOH)
Melt Point(°C) 256-266°C
Molecular Weight 294.400 g/mol
XLogP3 2.700
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 3
Rotatable Bond Count 3
Exact Mass 294.173 Da
Monoisotopic Mass 294.173 Da
Topological Polar Surface Area 36.400 Ų
Heavy Atom Count 22
Formal Charge 0
Complexity 412.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 4
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 1

Citations of This Product

How to Cite Aladdin Scientific Products?
1. Huan Xue, Hao-Jie Xing, Bin Wang, Chao Fu, Yu-Shan Zhang, Xi Qiao, Chao Guo, Xiao-Li Zhang, Bin Hu, Xin Zhao, Li-Jiao Deng, Xiao-Chan Zhu, Yi Zhang, Yun-Feng Liu.  (2023)  Cinchonine, a Potential Oral Small-Molecule Glucagon-Like Peptide-1 Receptor Agonist, Lowers Blood Glucose and Ameliorates Non-Alcoholic Steatohepatitis.  Drug Design Development and Therapy,     
2. Zhi-Yuan Zhang, Li-Li Rui, Ya-Li Lin, Hui-Dan Zhang, Ji-Ming Ou, Jian-Feng He, Quan-Zhou Wu.  (2021)  Preparation of ordered macroporous molecularly imprinted polymers and their applications in purifying cinchona alkaloids from cinchona extract.  POLYMER INTERNATIONAL,  70  (9): (1344-1355). 
3. Yuan Tan, Lijing Jing, Yonghong Ding, Tianxin Wei.  (2015)  A novel double-layer molecularly imprinted polymer film based surface plasmon resonance for determination of testosterone in aqueous media.  APPLIED SURFACE SCIENCE,  342  (84). 
4. Li Liu, Xuecai Tan, Xiaoxue Fang, Yuexin Sun, Fuhou Lei, Zaiyin Huang.  (2012)  Electrochemical Sensor Based on Molecularly Imprinted Polymer Film Prepared with Functional Abietic-Type Acids as Cross-Linker for the Determination of Quinine.  ELECTROANALYSIS,  24  (7): (1647-1654). 

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