Praeruptorin A

Base Information

• Chemical Name: Praeruptorin A
• CAS No.: 73069-25-7
• Molecular Formula: C₂₁H₂₂O₇
• Molecular Weight: 386.401
• Hs Code.: 29329990
• Mol file: 73069-25-7.mol

Synonyms:(-)-pareruptorin A;

Chemical Property of Praeruptorin A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.574
• Boiling Point: 486.817 °C at 760 mmHg
• Flash Point: 211.534 °C
• PSA: 92.04000
• Density: 1.289 g/cm³
• LogP: 3.44620
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

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

(-)-PraeruptorinA ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Praeruptorin A is used in the treatment of cardiac diseases, extracted from Peucedani Radix, it exhibits anti-hypertensive effects. Also a potential anti-tumor agent due to the ability to modulate P-glycoprotein (Pgp), overexpression in MDR tumor cells.

Technology Process of Praeruptorin A

There total 9 articles about Praeruptorin A 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: 74.8%

(E)-2-methylbut-2-enoyl chloride (35660-94-7) + (+/-)-trans-4'-acetylkhellactone (4955-21-9,35345-45-0,107080-28-4,112346-42-6,118492-19-6,118492-23-2) → (+/-)-trans-4'-acetyl=3'-tigloylkhellactone (14017-71-1,73069-25-7,73069-27-9,81740-05-8,112346-41-5,118492-20-9,118492-26-5,127643-75-8)

Guidance literature:

In benzene; Heating;

DOI:10.1248/cpb.43.859

Reference yield: 21.1%

(Z)-2-methyl-2-butenoyl chloride (35660-94-7,49651-33-4,62529-65-1) + (+/-)-cis-4'-acetylkhellactone (4955-21-9,35345-45-0,107080-28-4,112346-42-6,118492-19-6,118492-23-2) → (+/-)-4'-O-acetyl-3'-O-angeloyl-cis-khellactone (14017-71-1,73069-25-7,73069-27-9,81740-05-8,112346-41-5,118492-20-9,118492-26-5,127643-75-8)

Guidance literature:

In benzene;

DOI:10.1248/cpb.36.4221

Reference yield:

seseline (523-59-1) → (+/-)-cis-4'-acetyl-3'-tigloylkhellactone (14017-71-1,73069-25-7,73069-27-9,81740-05-8,112346-41-5,118492-20-9,118492-26-5,127643-75-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent Turnov_. / OsO₄, N-methylmorpholine-N-oxide dihydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 72 h / Ambient temperature

2: 65 percent Turnov_. / BF₃*Et₂O / tetrahydrofuran / 2.8 h / Ambient temperature

3: 86 percent Turnov_. / 4-pyrrolidinopyridine, 1,3-dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 125 h / Heating

With osmium(VIII) oxide; boron trifluoride diethyl etherate; 4-pyrrolidin-1-ylpyridine; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.3987/R-1987-05-1239

upstream raw materials:

Angelic acid

(+/-)-cis-4'-acetylkhellactone

(Z)-2-methyl-2-butenoyl chloride

seseline

Downstream raw materials:

(±)-cis-khellactone

(-)-cis-(3'S,4'S)-khellactone

(+)-(3'S,4'R)-trans-khellactone

(-)-(3'R,4'S)-3'-angeloylkhellactone

Refernces

• 1、 Takeuchi,Kasama,Mayuzumi,Tamaru,Fukaya,Ohno,Tobinaga. "The antagonist effects of compounds derived from khellactone on platelet-activating factor". . p. 4221 - 4224. Retrieved 2007/10/02.