511-98-8 Usage
Description
This alkaloid from Solanum dulcamara forms colourless plates when crystallized from MeOH. It is laevorotatory with [α]D - 50° (c 0.4, CHCI3). The alkaloid forms the O,N-diformyl derivative which exists as two rotational isomers, the trans with m.p. 222-4°C; [α]20D - 21.2° (CHCI3) and the cis isomer with m.p. 202-4°C; [α]20D - 69.6° (CHCI3).
Uses
Soladulcidine is a steroidal glycoalkaloid extracted from tomato leaves and berries and can induce craniofacial malformations in hamsters.
References
Schreiber., Planta Med., 6,93 (1958) Alkemeyer, Sandor., Naturwiss., 46, 207 (1959) Schreiber, Adam., Experientia, 17,13 (1961) Schreiber, Adam., Annalen, 666, 155 (1963) Synthesis: Adam, Schreiber., Experientia, 21,471 (1965) Adam, Schreiber., Tetrahedron, 22, 3591 (1966) Absolute configuration: Boll, von Philipsborn., Acta Chem. Scand., 19,1365 (1965)
Check Digit Verification of cas no
The CAS Registry Mumber 511-98-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 1 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 511-98:
(5*5)+(4*1)+(3*1)+(2*9)+(1*8)=58
58 % 10 = 8
So 511-98-8 is a valid CAS Registry Number.
InChI:InChI=1/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3/t16-,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
511-98-8Relevant articles and documents
Concise large-scale synthesis of tomatidine, a potent antibiotic natural product
Boudreault, Pierre-Luc,Normandin, Chad
, (2021/10/12)
Tomatidine has recently generated a lot of interest amongst the pharmacology, medicine, and biology fields of study, especially for its newfound activity as an antibiotic agent capable of targeting multiple strains of bacteria. In the light of its low natural abundance and high cost, an efficient and scalable multi-gram synthesis of tomatidine has been developed. This synthesis uses a Suzuki–Miyaura-type coupling reaction as a key step to graft an enantiopure F-ring side chain to the steroidal scaffold of the natural product, which was accessible from low-cost and commercially available diosgenin. A Lewis acid-mediated spiroketal opening followed by an azide substitution and reduction sequence is employed to generate the spiroaminoketal motif of the natural product. Overall, this synthesis produced 5.2 g in a single pass in 15 total steps and 15.2% yield using a methodology that is atom economical, scalable, and requires no flash chromatography purifications.
