98569-64-3

Basic information

• Product Name: (22R)-1α,3β,22,27-Tetrahydroxyergosta-5,24-diene-26-oic acid 26,22-lactone
• Synonyms: (+)-1α,3β,27-Trihydroxy-5,24-withadienolide;(+)-Pubesenolide;(22R)-1α,3β,22,27-Tetrahydroxyergosta-5,24-diene-26-oic acid 26,22-lactone;[22R,(+)]-1α,3β,22,27-Tetrahydroxyergosta-5,24-dien-26-oic acid 26,22-lactone;[22R,(+)]-1α,3β,22,27-Tetrahydroxyergosta-5,24-diene-26-oic acid 26,22-lactone;Pubesenolide;Sominone
• CAS NO: 98569-64-3
• Molecular Formula: C₂₈H₄₂O₅
• Molecular Weight: 458.63008
• Mol File: 98569-64-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (22R)-1α,3β,22,27-Tetrahydroxyergosta-5,24-diene-26-oic acid 26,22-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (22R)-1α,3β,22,27-Tetrahydroxyergosta-5,24-diene-26-oic acid 26,22-lactone(98569-64-3)
• EPA Substance Registry System: (22R)-1α,3β,22,27-Tetrahydroxyergosta-5,24-diene-26-oic acid 26,22-lactone(98569-64-3)

Safety Data

• Hazardous Substances Data: 98569-64-3(Hazardous Substances Data)

Usage

Uses

Pubesenolide is a steroidal sapogenin that was found to improve memory impairments and increase axonal density in Alzheimer’s disease in model mice.

Synthetic route

C34H56O5Si (1185317-38-7) → (20S,22R)-1α,3β,27-trihydroxywitha-5,24(25)-dienolide (98569-64-3)

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran for 3h; Reflux; Inert atmosphere;	79%

(20S,22R)-3β-[(O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-27-[(O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl)oxy]-1α-hydroxywitha-5,24(25)-dienolide → D-glucose (50-99-7) + (20S,22R)-1α,3β,27-trihydroxywitha-5,24(25)-dienolide (98569-64-3)

Conditions	Yield
With naringinase In aq. acetate buffer at 20℃; for 72h; pH=4.3; Enzymatic reaction;	A 1 mg B 0.9 mg

Upstream product

• 1185317-38-7 C₃₄H₅₆O₅Si 

Relevant articles and documents

Steroidal constituents isolated from the seeds of Withania somnifera

A new withanolide glycoside (1), two new ergostanol glycosides (2 and 3), and a new furostanol glycoside (4), along with nine known steroidal derivatives (5–12) were isolated from the seeds of Withania somnifera. The structures of the new compounds were determined using spectroscopic analysis and hydrolysis. The cytotoxic activities of the isolated compounds were evaluated against Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, and HL-60 human promyelocytic leukemia cells. Only 12 exhibited cytotoxic activity against these cell lines with IC50 values of 0.38, 0.54, and 1.5 μM, respectively.