Agrocybenine

Catalog Number	ACM178764926
CAS Number	178764-92-6
Structure
Synonyms	1,2,3,5-Tetrahydro-2,2,5,5,7-pentamethyl-6H-pyrrolo[3,2-b]pyridin-6-one
Molecular Weight	206.28
InChI	InChI=1S/C12H18N2O/c1-7-9-8(6-11(2,3)14-9)13-12(4,5)10(7)15/h14H,6H2,1-5H3
InChI Key	OTBGQBSPIWKINO-UHFFFAOYSA-N
Purity	95%+
Complexity	400
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
Exact Mass	206.141913202
Heavy Atom Count	15
Hydrogen Bond Acceptor Count	3
Hydrogen Bond Donor Count	1
Monoisotopic Mass	206.141913202
PhysicalState	Powder
Rotatable Bond Count	0
Topological Polar Surface Area	41.5 Ų

Case Study

Piperidine Alkaloids with Multiple Skeletons Including Agrocybenine

Qi-Bin Chen, et al. J. Nat. Prod. 2018, 81(6), 1474-1482

Fifteen piperidine alkaloids were successfully isolated from Anacyclus pyrethrum. Coexisting compounds 4,6,6-trimethyl-5,6-dihydro-2(1H)-pyridone (12) and 3,5,5-trimethyl-1,5-dihydro-2H-pyrrol-2-one (13) may serve as biosynthetic precursors for 1-11. Among them, agrocybenine (11) can be further used to synthesize compounds pyracyclumines H (8) and pyracyclumine I (9). The results showed that compounds 1-13 (including agrocybenine) exhibited weak inhibitory effects on MLL1 protein-protein interactions.
Extraction and Isolation of piperidine alkaloids
· A total of 4.5 kg of A. pyrethrum roots were ground into powder and subjected to extraction using acetone/MeOH (1:1, 10 L × 8, 24 hours each) at room temperature. The resultant crude extract (1.2 kg) was dissolved in 1 L of 5% HCl, filtered, and yielded a 5% HCl-soluble aqueous solution. This solution was then treated with CH2Cl2 to eliminate nonalkaloid components.
· The purified aqueous solution was made basic by adding saturated NaHCO3 solution in an ice water bath until reaching a pH of 10. The alkaline solution was then further extracted with CH2Cl2, resulting in a total of 660 g of alkaloids.
· After partitioning the total alkaloids using MeOH/n-hexane (1:1, 2 L), a MeOH-soluble fraction of 140 g was obtained. This MeOH fraction was dissolved in 1 L of EtOAc, filtered, and produced an EtOAc-soluble fraction weighing 70 g. The latter was subjected to fractionation using a Waters autopurification system, leading to the isolation of fractions Fr.1 (2.1 g, eluting between 9.0 and 14.0 minutes).
· Fr.1 (2.1 g) was fractionated by semipreparative HPLC to give Fr.1.1 (300 mg, 21.0-26.5 min). Fr.1.1 (300 mg) was further separated by semipreparative HPLC to afford Fr.1.1.1 (23.0-29.0 min). Fr1.1.1 was purified by semipreparative HPLC to obtain compound 11 (176.7 mg, tR 9.5 min).

Custom Q&A

What is the chemical formula for Agrocybenine?

The chemical formula for Agrocybenine is C12H18N2O.

What is the molecular weight of Agrocybenine?

The molecular weight of Agrocybenine is 206.28.

What is the boiling point of Agrocybenine?

The boiling point of Agrocybenine is predicted to be 288.1±40.0 °C.

In what solvents is Agrocybenine soluble?

Agryocybenine is soluble in Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.

What form does Agrocybenine take?

Agrocybenine is in the form of a powder.

What is the predicted pKa value of Agrocybenine?

The predicted pKa value of Agrocybenine is 7.06±0.60.

What is the color of Agrocybenine?

Agrocybenine is yellow in color.

How is Agrocybenine defined in ChEBI?

Agrocybenine is defined in ChEBI as a pyrrolopyridine.

Can Agrocybenine be used in chemical synthesis?

Yes, Agrocybenine can be used in chemical synthesis.

What are some of the common synonyms for Agrocybenine?

Some synonyms for Agrocybenine include 1,2,3,5-Tetrahydro-2,2,5,5,7-pentamethyl-6H-pyrrolo[3,2-b]pyridin-6-one; and 6H-Pyrrolo[3,2-b]pyridin-6-one, 1,2,3,5-tetrahydro-2,2,5,5,7-pentamethyl-.

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