Rotundine

Base Information

• Chemical Name: Rotundine
• CAS No.: 2934-97-6
• Molecular Formula: C21H25NO4
• Molecular Weight: 355.434
• Hs Code.: 29339900
• UNII: 78F8583LNQ
• DSSTox Substance ID: DTXSID20864207
• Nikkaji Number: J31.846I
• Wikipedia: Tetrahydropalmatine
• Wikidata: Q27163527
• Pharos Ligand ID: AHBM2FCK4A36
• Metabolomics Workbench ID: 125232
• ChEMBL ID: CHEMBL187892
• Mol file: 2934-97-6.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 Rotundine

Chemical Property:

• Vapor Pressure: 1.76E-09mmHg at 25°C
• Melting Point: 155℃
• Refractive Index: 1.608
• Boiling Point: 482.9 °C at 760 mmHg
• PKA: 6.53±0.20(Predicted)
• Flash Point: 138.7 °C
• PSA: 40.16000
• Density: 1.23 g/cm³
• LogP: 3.31440
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
• 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

L-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
• Description: Tetrahydropalmatine can be prepared from the total bases of tetrahydroxy berberine. Tetrahydropalmatine can be used to prepare palmatine. Palmatine has a broad-spectrum antibacterial effect, especially against Candida albicans. It can be used clinically to treat gynecological inflammation, bacillary dysentery, enteritis, respiratory and urinary tract infections, surgical infections, and conjunctivitis. Palmatine can also enhance the relaxation of the body's norepinephrine smooth muscle. Tetrahydropalmatine, an active component isolated from corydalis, acts through inhibition of amygdaloid release of dopamine to inhibit an epileptic attack in rats.
• Uses: DL-Tetrahydropalmatine is the main active substance of the Chinese herb corydalis which induces hypotension and bradycardia in rats through the antagonism of striatal dopamine D2 receptor. analgesic, hypnotic, papaverine-like

Technology Process of Rotundine

There total 147 articles about Rotundine 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:

2,3,9,10-tetramethoxy-isoquino[3,2-a]isoquinolinylium; bromide

diazomethane

2,3-dihydroxy-9,10-dimethoxyprotoberberine

(+/-)-12-bromotetrahydropalmatine

Downstream raw materials:

palmatine iodide

(R)-(+)-tetrahydropalmatine

tetrahydropalmatine

L-tetrahydropalmatine

Refernces

• 1、 Calderwood et al.. "-". . p. 682,683,685. Retrieved 1971.
• 2、 TOMITA,IBUKA,TSUYAMA. "STUDIES ON THE ALKALOIDS OF MENISPERMACEOUS PLANTS. CCVI. ALKALOIDS OF". . p. 776 - 778. Retrieved 1964.
• 3、 -. "Method for synthesizing tetrahydroberberine and derivatives thereof". Paragraph 0094-0099. . Retrieved 2021/07/08.
• 4、 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.