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| | [S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide Basic information |
| Product Name: | [S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide | | Synonyms: | [S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide;(3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]isobenzofuran-1(3H)-one;Desmethylnarcotine;(3S)-3-[(5R)-4-hydroxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-2-benzofuran-1-one;(3S)-3-[(5R)-4-hydroxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-isobenzofuran-1-one;narcotoline;Noscapine Impurity 6(Narcotoline);1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (3S)- | | CAS: | 521-40-4 | | MF: | C21H21NO7 | | MW: | 399.39 | | EINECS: | 208-313-6 | | Product Categories: | | | Mol File: | 521-40-4.mol | ![[S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide Structure](CAS/GIF/521-40-4.gif) |
| | [S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide Chemical Properties |
| Melting point | 202° | | alpha | D20 -189° (0.1 g in 25 ml chloroform, 20 cm tube); D20 +5.8° (0.065 g in 5 ml 0.1N HCl in 20 cm tube) | | storage temp. | -20°C Freezer, Under inert atmosphere | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Solid | | color | Pale Yellow to Light Yellow |
| | [S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide Usage And Synthesis |
| Description | Wrede has obtained this alkaloid from the seed capsules of Papaver somniferum.
It crystallizes from aqueous MeOH in colourless rectangular rods and has [0:]5° -
189° (CHCI3) and + 5.8° (c 0.1 NiHCI). One phenolic hydroxyl group is present
in the molecule and the base forms the O-acetate, m.p. 208-9°C, giving a hydro_x0002_chloride as the monohydrate, m.p. 230-3°C (dry); [0:]5° + 94.8° (H 20). The
acid tartrate forms colourless needles which, decompose at 190-205°C and the
picrolonate has m.p. 202-3°C. On treatment with CH2N2, the alkaloid gives
Narcotine (q.v.). | | Uses | Desmethylnarcotine is an impurity of Narcotoline an opiate alkaloid and a structure analogue of Nascapine (N882000), an antitussive agent. Noscapine (N882000) metabolite. | | Definition | ChEBI: Narcotoline is a member of isoquinolines. | | References | Wrede., r;hem. Zentr., I, 2611 (1937) Wrede., ibid, II, 863 (1938) |
| | [S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide Preparation Products And Raw materials |
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