10010. Visnadine

Nomenclature

CAS number: 477-32-7
(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; 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-(α-methylbutyrate); 3,4,5-trihydroxy-2,2-dimethyl-6-chromanacrylic acid δ-lactone 4-acetate 3-(2-methylbutyrate); 4′-acetoxy-3′-(α-methylbutyryloxy)-2′,2′-dimethyldihydropyrano(7,8:6′,5′)coumarin; 3-(α-methylbutyryloxy)-4-acetoxy-3,4-dihydroseseline; Cardine (Marshall); Carduben (Madaus); Vibeline (Bellon); Visnamine (Chinoin).
C21H24O7; mol wt 388.41.
C 64.94%, H 6.23%, O 28.83%.

Description and 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).

Chemical structure

Properties

Needles from light petr, or ether + hexane, mp 85-88°. [α]D20 +9.2° (alc), [α]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).

Derivative

(±)-Form.

Properties

Crystals from petr ether, mp 150-152° (Shanbhag).

Therapeutic Category

Vasodilator (coronary).

Keywords

Vasodilator (Coronary)