D-Tetrahydropalmatine

Base Information

• Chemical Name: D-Tetrahydropalmatine
• CAS No.: 3520-14-7
• Molecular Formula: C21H25NO4
• Molecular Weight: 355.434
• UNII: 7BLG4NXS54
• DSSTox Substance ID: DTXSID80359548
• Nikkaji Number: J357.052E
• Wikipedia: Tetrahydropalmatine
• Wikidata: Q27268022
• Metabolomics Workbench ID: 128235
• ChEMBL ID: CHEMBL2334889
• Mol file: 3520-14-7.mol

Synonyms:(+-)-isomer of tetrahydropalmatine;(R)-isomer;corydalis B of tetrahydropalmatine;(S)-isomer of tetrahydropalmatine;5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo(a,g)quinolizine;corydalis B;gindarin;HCl of tetrahydropalmatine;HCl(+-)-isomer of tetrahydropalmatine;HCl(R)-isomer of tetrahydropalmatine;HCl(S)-isomer of tetrahydropalmatine;levo-tetrahydropalmatine;rotundine;Rotundium;tetrahydropalmatine;tetrahydropalmitine

Chemical Property of D-Tetrahydropalmatine

Chemical Property:

• Melting Point: 138-139 °C
• Boiling Point: 482.9oC at 760mmHg
• PKA: 6.53±0.20(Predicted)
• Flash Point: 138.7oC
• PSA: 40.16000
• Density: 1.23g/cm3
• LogP: 3.31440
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 355.17835828
• Heavy Atom Count: 26
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

D-Tetrahydropalmatine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC
• Isomeric SMILES: COC1=C(C2=C(C[C@@H]3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC
• Uses: D-Tetrahydropalmatine is an alkaloid isolated from a traditional Chinese herb Rhizoma Corydalis (yanhusuo). D-Tetrahydropalmatine inhibits dopamine and serotonin uptake of synaptosomes in the rat brai n. D-Tetrahydropalmatine also shows inhibitory effects on acetylcholinesterase and butyrylcholinesterase. D-Tetrahydropalmatine is an alkaloid isolated from a traditional Chinese herb Rhizoma Corydalis (yanhusuo). D-Tetrahydropalmatine inhibits dopamine and serotonin uptake of synaptosomes in the rat brain. D-Tetrahydropalmatine also shows inhibitory effects on acetylcholinesterase and butyrylcholinesterase.

Technology Process of D-Tetrahydropalmatine

There total 64 articles about D-Tetrahydropalmatine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline (26067-60-7) → tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-1,1'-bis{(R)-4,5-dihydro-3H-dinaphtho[1,2-c:2',1'-e]-phosphepino}ferrocene; hydrogen; acetic acid; potassium bromide; In dichloromethane; at 25 ℃; for 72h; under 60804.1 Torr; enantioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.1c00602

Reference yield: 92.0%

(13aS)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizin-5-ol (870282-81-8) → tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 19h;

DOI:10.1021/jo051554t

Reference yield: 56.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1356336-76-9) → tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8)

Guidance literature:

formaldehyd; (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; With trifluoroacetic acid; In toluene; at 140 ℃; for 0.5h; Microwave irradiation;

With sodium hydroxide; In water; pH=8;

DOI:10.1016/j.tet.2011.11.046

upstream raw materials:

diazomethane

(-)-isocorypalmine

corypalmine

(+/-)-tetrahydropalmatine

Downstream raw materials:

(S)-(-)-8-oxoxylopinine

(-)-isocorypalmine

2,3,9,10-tetramethoxy-13aα-berbine; hydrochloride

D-tetrahydropalmatine

Refernces

• 1、 -. "Method for synthesizing tetrahydroberberine and derivatives thereof". Paragraph 0094-0099. . Retrieved 2021/07/08.
• 2、 Sun, Haifeng,Zhu, Liyuan,Yang, Huicui,Qian, Wangke,Guo, Lin,Zhou, Shengbin,Gao, Bo,Li, Zeng,Zhou, Yu,Jiang, Hualiang,Chen, Kaixian,Zhen, Xuechu,Liu, Hong. "Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D1, D2 and serotonin 5-HT1A multi-action profile". supporting information. p. 856 - 868. Retrieved 2013/03/13.