Title: Visnadine
CAS Registry Number: 477-32-7
CAS Name: (2R)-2-Methylbutanoic acid (9R,10R)-10-(acetyloxy)-9,10-dihydro-8,8-dimethyl-2-oxo-2H,8H-benzo[1,2-b:3,4-b¢]dipyran-9-yl ester
Additional Names: 2-methylbutyric acid 9-ester with 9,10-dihydro-9,10-dihydroxy-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b¢]dipyran-2-one acetate; 8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b¢]dipyran-9,10-diyl-10-acetate-9-(a-methylbutyrate); 3,4,5-trihydroxy-2,2-dimethyl-6-chromanacrylic acid d-lactone 4-acetate 3-(2-methylbutyrate); 4¢-acetoxy-3¢-(a-methylbutyryloxy)-2¢,2¢-dimethyldihydropyrano(7,8:6¢,5¢)coumarin; 3-(a-methylbutyryloxy)-4-acetoxy-3,4-dihydroseseline
Trademarks: Cardine (Marshall); Carduben (Madaus); Vibeline (Bellon); Visnamine (Chinoin)
Molecular Formula: C21H24O7
Molecular Weight: 388.41
Percent Composition: C 64.94%, H 6.23%, O 28.83%
Literature References: Isoln from seeds of Ammi visnaga L., Umbelliferae (Bishop's weed): Smith et al., Science 115, 520 (1952); eidem, J. Am. Chem. Soc. 79, 3534 (1957); Smith, Haber; Smith, Hosansky, US 2816118; US 2980699 (1957, 1961 both to Penick); Le Men, US 2995574 (1961 to Lab. Roger Bellon); Baddar et al., J. Chem. Soc. 1963, 4522. Synthesis of (±)-form: Shanbhag et al., Tetrahedron 21, 3591 (1965). Pharmacology and toxicology: Nkondi et al., Therapie 21, 1267 (1966); Erbring et al., Arzneim.-Forsch. 17, 283 (1967); Eyraud, Aurousseau, ibid. 23, 201 (1973).
Properties: Needles from light petr, or ether + hexane, mp 85-88°. [a]D20 +9.2° (alc), [a]D30 +42.5° (c = 2 in dioxane). Slightly sol in water; quite sol in ethanol, methanol. Very sol in chloroform, acetone, ether, benzene, DMF. LD50 in mice (mg/kg): 2240 orally; >370 s.c. (Erbring).
Melting point: mp 85-88°
Optical Rotation: [a]D20 +9.2° (alc); [a]D30 +42.5° (c = 2 in dioxane)
Toxicity data: LD50 in mice (mg/kg): 2240 orally; >370 s.c. (Erbring)
Derivative Type: (±)-Form
Properties: Crystals from petr ether, mp 150-152° (Shanbhag).
Melting point: mp 150-152° (Shanbhag)
Therap-Cat: Vasodilator (coronary).
Keywords: Vasodilator (Coronary). |