Solanidine

Solanidine

Names
Other names Solatubin; Solatubine; Solanid-5-en-3beta-ol, Solanid-5-en-3-beta-ol
Identifiers
CAS Number	80-78-4
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:28374
ChemSpider	59150
ECHA InfoCard	100.001.191
PubChem CID	65727
InChI InChI=1S/C27H43NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1 Key: JVKYZPBMZPJNAJ-OQFNDJACSA-N InChI=1/C27H43NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1 Key: JVKYZPBMZPJNAJ-OQFNDJACBI
SMILES C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O)C)C)C C[C@@H]1CN2[C@@]3([H])C[C@@]4([H])[C@]5([H])CCC6=C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3([H])[C@H](C)[C@@]2([H])CC1
Properties
Chemical formula	C27H43NO
Molar mass	397.65 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Solanidine is a poisonous steroidal alkaloid chemical compound that occurs in plants of the Solanaceae family, such as potato and Solanum americanum. Human ingestion of solanidine also occurs via the consumption of the glycoalkaloids, α-solanine and α-chaconine, present in potatoes. The sugar portion of these glycoalkaloids hydrolyses in the body, leaving the solanidine portion. Solanidine occurs in the blood serum of normal healthy people who eat potato, and serum solanidine levels fall markedly once potato consumption ceases. Solanidine from food is also stored in the human body for prolonged periods of time, and it has been suggested that it could be released during times of metabolic stress with the potential for deleterious consequences. Solandine is responsible for neuromuscular syndromes via cholinesterase inhibition.

Solanidine is a very important precursor for the synthesis of hormones and some pharmacologically active compounds.

In 1994 Gunic and coworkers reported the electrochemical oxidation of 3β-acetoxy-solanidine in CH3CN/CH2Cl2 1/1 with pyridine as a base. The corresponding iminium salts 2 and 3 were obtained in a 1/1 ratio in good yield. Performing this electrochemical reaction in DCM with pyridine gives 3 in 95% yield, while the same reaction in acetone gives iminium salt 2 in 95% yield. Iminium ion 2 can be isomerized to the thermodynamically more stable enamine 5. THis isomerization is believed to proceed via enamine 4, which is the kinetic product.