CID 5148108

Base Information

• Chemical Name: CID 5148108
• CAS No.: 57444-62-9
• Molecular Formula: C37H40 O9
• Molecular Weight: 628.719
• Hs Code.: 29329990
• European Community (EC) Number: 637-354-6
• Wikidata: Q104665539
• Wikipedia: Resiniferatoxin
• Mol file: 57444-62-9.mol

Synonyms:57444-62-9;Resiniferatoxin (RL 9);(13-Benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl)methyl 2-(4-hydroxy-3-methoxyphenyl)acetate

Chemical Property of CID 5148108

Chemical Property:

• Vapor Pressure: 7.41E-25mmHg at 25°C
• Boiling Point: 768.7°Cat760mmHg
• PKA: 9.85±0.20(Predicted)
• Flash Point: 240.3°C
• PSA: 120.75000
• Density: 1.35g/cm³
• LogP: 4.74470
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO to 100mM and to 50mM in ethanol
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 628.26723285
• Heavy Atom Count: 46
• Complexity: 1330

Purity/Quality:

98%,99%, ^*data from raw suppliers

Resiniferatoxin from Euphorbia poisonii, ~95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: T
• Statements: 25-35
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC2(C3C4C1(C5C=C(C(=O)C5(CC(=C4)COC(=O)CC6=CC(=C(C=C6)O)OC)O)C)OC(O3)(O2)CC7=CC=CC=C7)C(=C)C
• Recent EU Clinical Trials: A randomized, double-blind, placebo-controlled, Phase III trial to
• Description: Resiniferatoxin (57444-62-9) is an ultrapotent TRPV1 activator (Ki=43 pM).1 Resiniferatoxin is 100-10,000 fold more potent than capsaicin for most responses yet displays a spectrum of activity distinct from capsaicin.2 A potent sensory neuron excitotoxin.3 Induces a long lasting analgesia in a rodent model of burn pain.4 SEVERE IRRITANT – HANDLE WITH CARE
• Uses: Resiniferatoxin has been used as an agonist to transient receptor potential vanilloid 2 (TRPV2): for complex preparation for cryo-electron microscopy structural studies to test its effect towards immune responses to?P.?aeruginosa in sensory neurons associated with the cornea to study its effects in the denervation of the peripheral sensory nerves in psoriatic mice

Technology Process of CID 5148108

There total 43 articles about CID 5148108 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: 92.0%

2-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)acetic acid (1344662-01-6) + C31H39ClO5Si → resiniferatoxin (57444-62-9)

Guidance literature:

2-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)acetic acid; C₃₁H₃₉ClO₅Si; With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 5.66667h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.583333h;

DOI:10.1021/jacs.7b10177

Reference yield: 67.0%

Homovanillic acid (306-08-1) + Resininiferonol-9-13-14-ortho-phenyl acetate → resiniferatoxin (57444-62-9)

Guidance literature:

With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/1099-0690(20021)2002:1<71::AID-EJOC71>3.0.CO;2-C

Reference yield:

C17H28O5 → resiniferatoxin (57444-62-9)

Guidance literature:

Multi-step reaction with 32 steps

1.1: Dowex 50W / tetrahydrofuran; water / 12 h / 90 °C

2.1: pyridine / dichloromethane / 1 h / 0 - 20 °C

3.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C

5.2: 0.42 h

6.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C

7.1: triethylamine / dichloromethane / 1.25 h / 0 °C

8.1: dmap / toluene / 1.5 h / 20 °C / Darkness

9.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation

10.1: potassium carbonate / methanol / 7.5 h / 0 °C

11.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C

12.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C

13.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C

14.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere

15.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere

16.1: triethylamine / dichloromethane / 1.5 h / 0 °C

17.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C

18.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere

18.2: (+)-CSA / 0.33 h / 50 °C

19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

20.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere

20.2: 0.5 h / 20 °C / Inert atmosphere

21.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere

22.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation

23.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C

23.2: 1.5 h

24.1: dmap; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C

25.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C

26.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C

27.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

28.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere

28.2: 0.33 h / -20 °C / Inert atmosphere

29.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C

30.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C

31.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C

31.2: 0.42 h / 150 °C

31.3: 0.5 h / 0 - 20 °C

32.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C

32.2: 0.58 h / 0 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; hydrogenchloride; dmap; [2,2]bipyridinyl; selenium(IV) oxide; sodium tetrahydroborate; N-Bromosuccinimide; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; lead(IV) tetraacetate; sodium hexamethyldisilazane; acetic anhydride; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; lithium hexamethyldisilazane; 1,1'-azobis(1-cyanocyclohexanenitrile); In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; hexane; dichloromethane; water; N,N-dimethyl-formamide; chlorobenzene; toluene; acetonitrile; mineral oil; tert-butyl alcohol; benzene;

DOI:10.1021/jacs.7b10177

upstream raw materials:

Homovanillic acid

Refernces

• 1、 Fattorusso, Ernesto,Lanzotti, Virginia,Taglialatela-Scafati, Orazio,Tron, Gian Cesare,Appendino, Giovanni. "Bisnorsesquiterpenoids from Euphorbia resinifera Berg. and an expeditious procedure to obtain resiniferatoxin from its fresh latex". . p. 71 - 78. Retrieved 2007/10/03.