549-28-0 Usage
Description
A Stephania alkaloid, this base is found in S. japonica Miers. It forms colourless
prisms from MeOH which contain solvent of crystallization, m.p. 75°C. The
solvent may be removed under vacuum when the dry alkaloid has a higher
melting point of 90-S°C. It is optically inactive and yields crystalline saits, e.g.
the hydrochloride, m.p. 150°C (dec.); platinichloride, orange prisms, m.p. 223°C
(dec.); methiodide, m.p. 220-loC and the methomethylsulphate, m.p. 235°C
after sintering at 227°C. The structure has recently been confirmed by a synthesis
which follows a route related to the biosynthetic pathway.
References
Kondo, Watanabe., J. Pharrn. Soc., Japan, 58,46 (1938)
Kondo, Takeda., Chern. Abstr., 49, 1076 (1955)
Synthesis:
Battersby et al., Chern. Cornrnun., 20, 1214 (1968)
Check Digit Verification of cas no
The CAS Registry Mumber 549-28-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 9 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 549-28:
(5*5)+(4*4)+(3*9)+(2*2)+(1*8)=80
80 % 10 = 0
So 549-28-0 is a valid CAS Registry Number.
InChI:InChI=1/C21H27NO4/c1-22-8-6-14-10-20(25-4)21(26-5)13-17(14)18-11-15(23-2)12-19(24-3)16(18)7-9-22/h10-13H,6-9H2,1-5H3
549-28-0Relevant articles and documents
Synthesis along Biosynthetic Pathways. Part 2. Synthesis of Protostephanine
Battersby, Alan R.,Bhatnagar, Akil K.,Hackett, Peter,Thornber, Craig W.,Staunton, James
, p. 2002 - 2009 (2007/10/02)
The dienone protostephanone (3) is synthesised by phenol coupling or by Pschorr cyclisation from readily prepared tetrahydroisoquinolines, and the corresponding dienols (17) and (18) are converted by rearrangement, fragmentation, and reduction into protostephanine (4).This sequence mimics the natural pathway to the alkaloid.