477-32-7

Basic information

• Product Name: CARDIN
• Synonyms: CARDIN;(alpha-methylbutyryloxy)-3’-acetoxy-4’-dihydro-3’,4’-seselin;2h,8h-benzo(1,2-b:3,4-b’)dipyran-2-one-acetate;2-methyl-,9-esterwith9,10-dihydro-9,10-dihydroxy-8,8-dimethyl-butyricaci;3-(alpha-methylbutyryloxy)-4-acetoxy-3,4-dihydroseseline;cardine;carduben;carduben-s
• CAS NO: 477-32-7
• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.41
• EINECS: 207-515-1
• Product Categories: Coumarins
• Mol File: 477-32-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 85-88°
• Boiling Point: 434.13°C (rough estimate)
• Flash Point: 206.9 °C
• Appearance: /
• Density: 1.2086 (rough estimate)
• Vapor Pressure: 2.74E-09mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: ?20°C
• CAS DataBase Reference: CARDIN(CAS DataBase Reference)
• NIST Chemistry Reference: CARDIN(477-32-7)
• EPA Substance Registry System: CARDIN(477-32-7)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 477-32-7(Hazardous Substances Data)

Usage

Originator

Vibeline ,Bellon ,France,1960

Uses

Visnadine is used as a coumarin scaffold for anti-inflammatory drug development, melanin biosynthetic inhibitory activity, anticellulite efficacy in female patient with cellulite blemish affected by fat accumulation or new anticellulite treatment.

Manufacturing Process

Ammi visnaga is a plant of the Umbelliferae family, which has been known and used for its therapeutic properties by the peoples of the Mediterranean basin since time immemorial.Visnadine may be extracted from the umbels of Ammi visnaga by an organic solvent having a boiling point less than 110°C. The resulting solution is concentrated first by heating in a water bath and then is allowed to stand some time at a temperature of about 20°C and if necessary is treated for separation of gummy constituents therefrom, after which the solution is concentrated under reduced pressure. Finally, the crude product is crystallized and separated by retaining it on a filter.This crude product may then, according to the process, be purified by mixing it with petroleum ether and allowing it to stand at ordinary temperature, then filtering it to obtain the pure visnadine.

InChI:InChI=1/C21H24O7/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/h7-11,18-19H,6H2,1-5H3/t11-,18-,19-/m1/s1

Upstream product

• 116-53-0 2-Methylbutanoic acid 
• 4955-21-9 (+/-)-cis-4'-acetylkhellactone 

Downstream Products

• 518-76-3 (+)-(3'S,4'R)-trans-khellactone 
• 54712-23-1 (-)-cis-(3'S,4'S)-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.