QUININE

Base Information

• Chemical Name: QUININE
• CAS No.: 511-98-8
• Molecular Formula: C27H45 N O2
• Molecular Weight: 415.66
• Mol file: 511-98-8.mol

Synonyms:5a-Solasodan-3b-ol (8CI); Solasodanol (6CI);Solasodine, 5a,6-dihydro-(7CI); 5a,25D-Solasodan-3b-ol; Megacarpidin; Megacarpidine;NSC 82181; Soladulcidin; Soladulcidine

Chemical Property of QUININE

Chemical Property:

• Vapor Pressure: 2.56E-13mmHg at 25°C
• Boiling Point: 527.2°C at 760 mmHg
• Flash Point: 272.7°C
• PSA: 41.49000
• Density: 1.1g/cm³
• LogP: 5.69560
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly, Heated)

Purity/Quality:

98.5% ^*data from raw suppliers

Soladulcidine tetraoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: This alkaloid from Solanum dulcamara forms colourless plates when crystallized from MeOH. It is laevorotatory with [α]D - 50° (c 0.4, CHCI3). The alkaloid forms the O,N-diformyl derivative which exists as two rotational isomers, the trans with m.p. 222-4°C; [α]20D - 21.2° (CHCI3) and the cis isomer with m.p. 202-4°C; [α]20D - 69.6° (CHCI3).
• Uses: Soladulcidine is a steroidal glycoalkaloid extracted from tomato leaves and berries and can induce craniofacial malformations in hamsters.

Technology Process of QUININE

There total 2 articles about QUININE 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:

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-azido-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1Hnaphtho[2',1':4,5]indeno[2,1-b]furan-4-yl acetate → soladulcidine (511-98-8) + tomatidine (77-59-8)

Guidance literature:

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-azido-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1Hnaphtho[2',1':4,5]indeno[2,1-b]furan-4-yl acetate; With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 23 ℃; for 1h;

With sodium hydroxide; In methanol; dichloromethane; at 23 ℃; for 2h;

DOI:10.3390/molecules26196008

Reference yield:

C29H46O4 → soladulcidine (511-98-8) + tomatidine (77-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium bromide; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 3 h / 23 °C

1.2: 5 h / 70 °C

2.1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 1 h / 23 °C

2.2: 2 h / 23 °C

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; sodium iodide; lithium bromide; In dichloromethane; acetonitrile;

DOI:10.3390/molecules26196008

Reference yield:

Soladulcidine (511-98-8) → N(3)-(2-Hydroxybenzylidene)-5α-solasodan-3β-amine (125540-53-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 66 percent / CrO₃, conc. H₂SO₄ / acetic acid; dioxane; H₂O / Ambient temperature

2: 91 percent / NH₂OH*HCl / methanol; H₂O / 1 h / Heating

3: 90 percent / H₂ / Pt / acetic acid / 12 h

4: 68 percent / ethanol / 0.17 h / 78 °C

5: 90 percent / N-chlorosuccinimide / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 95 percent / NaOCH₃ / methanol / 0.5 h / Ambient temperature

7: 16 mg / aq. HCl / methanol / 1 h / Heating

8: 64 percent / ethanol / 0.03 h / 60 °C

With chromium(VI) oxide; hydrogenchloride; N-chloro-succinimide; sulfuric acid; hydroxylamine hydrochloride; hydrogen; sodium methylate; platinum; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid;

Downstream raw materials:

(22R,25R)-3β-acetoxy-(5α)-spirosolane

(22S,25R)-3-Amino-22,26-epimino-N(3)-(2-hydroxybenzylidene)-5α-cholestan-16β-ol

(22S,25R)-3β-Amino-22,26-epimino-N(3)-(2-hydroxybenzylidene)-5α-cholestan-16β-ol

N(3)-(2-Hydroxybenzylidene)-5α-solasodan-3-amine

Refernces