Cryogenine

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Chemical compound

title: "Cryogenine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["alkaloids", "catechol-ethers", "lactones", "alkene-derivatives", "heterocyclic-compounds-with-5-rings", "nitrogen-heterocycles", "oxygen-heterocycles"] description: "Chemical compound" topic_path: "general/alkaloids" source: "https://en.wikipedia.org/wiki/Cryogenine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

::callout[type=note] the alkaloid from the plants in the genus Heimia ::

| Verifiedfields = changed | verifiedrevid = 460108663 | IUPAC_name = (10α)-4,5-dimethoxy-2-hydroxylythran-12-one | image = Cryogenine.svg | image_class = skin-invert-image | width = 200

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US =

| CAS_number_Ref = | CAS_number = 10308-13-1 | UNII_Ref = | UNII = OR77C8W8TA | ATC_prefix = none | PubChem = 5315204 | ChemSpiderID_Ref = | ChemSpiderID = 4474587 | ChEMBL_Ref = | ChEMBL = 1173218

| C=26 | H=29 | N=1 | O=5 | smiles = O=C/4O[C@H]5C[C@@H]1N(CCCC1)C@HC5 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = WCZWUYYJZVBKDZ-VMSBZHFZSA-N

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.

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

References

  1. (May 1994). "Heimia salicifolia: a phytochemical and phytopharmacologic review". Journal of Ethnopharmacology.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

alkaloidscatechol-etherslactonesalkene-derivativesheterocyclic-compounds-with-5-ringsnitrogen-heterocyclesoxygen-heterocycles