Cryogenine

Cryogenine
Clinical data
ATC code	none;
Identifiers
	IUPAC name (10α)-4,5-dimethoxy-2-hydroxylythran-12-one;
CAS Number	10308-13-1 ;
PubChem CID	5315204;
ChemSpider	4474587 ;
ChEMBL	ChEMBL1173218 ;
Chemical and physical data
Formula	C26H29NO5
Molar mass	435.512 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C/4O[C@H]5C[C@@H]1N(CCCC1)[C@H](c2cc(OC)c(OC)cc2c3c(O)ccc(c3)\C=C\4)C5;
	InChI InChI=1S/C26H29NO5/c1-30-24-14-19-20(15-25(24)31-2)22-13-18(12-17-5-3-4-10-27(17)22)32-26(29)9-7-16-6-8-23(28)21(19)11-16/h6-9,11,14-15,17-18,22,28H,3-5,10,12-13H2,1-2H3/b9-7-/t17-,18+,22+/m1/s1 ; Key:WCZWUYYJZVBKDZ-VMSBZHFZSA-N ;
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Cryogenine, also known as vertine or (10α)-4,5-dimethoxy-2-hydroxylythran-12-one, is a biphenylquinolizidine lactone alkaloid from the plants Sinicuichi (Heimia salicifolia) and H. myrtifolia. The compound has no psychoactive properties in humans up to 310 mg, but has shown anti-inflammatory activity similar to aspirin.[1]

The freebase form melts at 250–251 °C and is soluble in moderately polar organic solvents such as chloroform, methylene chloride, benzene, and methanol, but is insoluble in water and petroleum ether.

In the development of thin layer chromatography plates with diazotized p-nitroaniline spray, cryogenine produces a purple spot (as does sinicuichine, another biphenylquinolizidine lactone alkaloid found in Heimia species).

References

M. H. Malone, A. Rother (1994). "Heimia salicifolia: A phytochemical and phytopharmacologic review". J. Ethnopharmacol. 42 (3): 135–159. doi:10.1016/0378-8741(94)90080-9. PMID 7934084.

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[Malone-1] M. H. Malone, A. Rother (1994). "Heimia salicifolia: A phytochemical and phytopharmacologic review". J. Ethnopharmacol. 42 (3): 135–159. doi:10.1016/0378-8741(94)90080-9. PMID 7934084.

Cryogenine

See also

References