73069-25-7

Basic information

• Product Name: Praeruptorin A
• Synonyms: PRAERUPTORIN A;2-Butenoicacid, 2-methyl-, (9S, 10S)-10-(acetyloxy)-;9,10-dihydro-8,8-dimethyl-2-oxo-2H, 8H-;DL-Praeruptorin A;Praeruptorin A DL-Praeruptorin A;Praeruptorin A, 98%, from Peucedanum praeruptorum Dunn
• CAS NO: 73069-25-7
• Molecular Formula: C₂₁H₂₂O₇
• Molecular Weight: 386.398
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 73069-25-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 486.817 °C at 760 mmHg
• Flash Point: 211.534 °C
• Appearance: /
• Density: 1.28
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Praeruptorin A(CAS DataBase Reference)
• NIST Chemistry Reference: Praeruptorin A(73069-25-7)
• EPA Substance Registry System: Praeruptorin A(73069-25-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 73069-25-7(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C21H22O7/c1-6-11(2)20(24)27-19-18(25-12(3)22)16-14(28-21(19,4)5)9-7-13-8-10-15(23)26-17(13)16/h6-10,18-19H,1-5H3/b11-6-/t18-,19-/m1/s1

Upstream product

• 523-59-1 seseline 
• 518-76-3 (±)-cis-khellactone 
• 35660-94-7 (E)-2-methylbut-2-enoyl chloride 
• 4955-21-9 (+/-)-trans-4'-acetylkhellactone 
• 565-63-9 Angelic acid 
• 4955-21-9 (+/-)-cis-4'-acetylkhellactone 
• 80-59-1 Tiglic acid 
• 35660-94-7 (Z)-2-methyl-2-butenoyl chloride 

Downstream Products

• 518-76-3 (+)-(3'S,4'R)-trans-khellactone 
• 54712-23-1 (-)-cis-(3'S,4'S)-khellactone 
• 84579-96-4 (-)-(3'R,4'S)-3'-angeloylkhellactone 
• 518-76-3 (+)-cis-khellactone 
• 518-76-3 trans-kellactone 
• 518-76-3 (±)-cis-khellactone 

Relevant articles and documents

The antagonistic effects of khellactones on platelet-activating factor, histamine, and leukotriene D4

Khellactones of Peucedanum praeruptorum Duun., including praeruptorins A (= Pd-Ia, 2) and B (= Pd-II, 11), had an antagonistic effect specifically on platelet aggregation induced by platelet activating factor (PAF) among various aggregating agents examined, and represent a new class of PAF antagonists. We examined the effects of twenty compounds on PAF-induced platelet aggregation and on histamine- and leukotriene D4 (LTD4)-induced contractions in isolated guinea pig ileum. Compounds 2, (±)-cis-3',4'-diacetylkhellactone (3), (±)-cis-4'-acetyl-3'-crotonoylkhellactone (5), (±)-cis-4'-acetyl-3'-tetrolylkhellactone (6), (±)-cis-4'-acetyl-3'-tigloylkhellactone (7), (±)-cis-4'-acetyl-3'-(2''-methylbutyryl)khellactone (8), (±)-cis-3',4'-ditigloylkhellactone (10), and 11 all strongly inhibited PAF-induced platelet aggregation. (±)-cis-4'-Acetyl-3'-(2''-methyl-2''-dodecenoyl)khellactone (9), (±)-cis-4'-ethyl-3'-tigloylkhellactone (13), (±)-cis-4'-ethyl-3'-[N-(2''-triethylammonio)ethylcarbamoyl]khellacton e iodide (16), (±)-trans-3',4'-diacetylkhellactone (18), (±)-trans-4'-acetyl-3'-crotonoylkhellactone (19), (±)-trans-4'acetyl-3'-valerylkhellactone (20), (±)-trans-4'-acetyl-3'-isovalerylkhellactone (21), and (±)-trans-4'-acetyl-3'-tigloylkhellactone (22) were weakly inhibitory. Most of the compounds exhibited noncompetitive antagonist actions on histamine- and LTD4-induced contractions. The potencies of the antagonistic effects on histamine action were in the order 7 = 22 ≥ 2 = 8 = 10 > 6 = 11 = 13 ≥ 5 > 19 = 9 and those on LTD4 action were in the order 6 = 22 = 2 > 10 = 8 > 7 = 9 = 11 ≥ 13. Thus, compounds with potent PAF-antagonistic activities have the following features: cis isomers of khellactone at the C-3' and C-4' positions are more favorable than trans isomers, and the acyl moiety at the C-3' position of khellactone must be of an appropriate molecular size. In the case of histamine- and LTD4-antagonistic activities, both isomers show similar effects and acyl moieties of appropriate size are required at the C-3' and C-4' positions. These results are of interest in regard to the medicinal uses of Peucedanum species as a herbal drug.

SYNTHESIS OF (+/-)-PRAERUPTORIN A AND RELATED KHELLACTONE DERIVATIVES

The first synthesis of the pyranocoumarin natural product, (+/-)-praeruptorin A (= Pd-Ia), is described.A general method for the preparation of various khellactone derivatives is reported.