511-96-6

Usage

Uses

Used in Pharmaceutical Applications:
(25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL is used as a bioactive compound for its inhibitory activities against various enzymes, such as α-glucosidase, lipoxygenase, acetylcholinesterase, and butyrylcholinesterase. These inhibitory properties suggest potential applications in the treatment of diabetes, inflammation, and neurodegenerative diseases.
Used in Drug Development:
(25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL is used as a lead compound in drug development for its potential therapeutic effects. Its ability to inhibit multiple enzymes makes it a valuable starting point for the development of new drugs targeting a range of diseases and conditions.
Used in Nutraceutical Applications:
(25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL may also be used as an ingredient in the nutraceutical industry, where it could be incorporated into dietary supplements and functional foods for its potential health benefits.
Used in Cosmetics Industry:
Due to its potential anti-inflammatory and antioxidant properties, (25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL could be used as an active ingredient in the cosmetics industry, particularly in products aimed at skin health and anti-aging.

InChI:InChI=1/C27H44O4/c1-15-7-10-27(30-14-15)16(2)24-23(31-27)12-20-18-6-5-17-11-21(28)22(29)13-26(17,4)19(18)8-9-25(20,24)3/h15-24,28-29H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21-,22-,23+,24+,25+,26+,27?/m1/s1

Synthetic route

26-O-β-D-glucopyranosyl-(25R)-5α-furostane-2α,3β,22ξ,26-tetrol 3-O-α-L-rhamnopyranosyl(1->2)-β-D-glucopyranoside → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 1h; Heating;	88.7%

2α-acetoxy-5α-spirostan-3β-ol (2781-69-3) → gitogenin (511-96-6)

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane at 20℃;	85%

26-O-β-D-glucopyranosyl-(25R)-5α-furostane-2α,3β,22ξ,26-tetrol 3-O-β-D-xylopyranosyl(1->4)-β-D-glucopyranoside → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 1h; Heating;	76%

26-O-β-D-glucopyranosyl-(25S)-5α-furostane-2α,3β,22ξ,26-tetrol 3-O-α-L-rhamnopyranosyl(1->2)-β-D-glucopyranoside → gitogenin (511-96-6) + (25S)-5α-spirostane-2α,3β-diol (6811-13-8)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 1h; Heating;	A 28.4% B 54.1%

trigoneoside Ib → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 1h; Heating;	19%

(25R)-2α,3β-diacetoxy-spirost-4-ene (119008-70-7) → gitogenin (511-96-6)

Conditions	Yield
With acetic acid; ethyl acetate; platinum Hydrogenation;

(25R)-2α,3β-diacetoxy-5α,14β-spirostan-15-one → gitogenin (511-96-6)

Conditions	Yield
With ethanol; hydrazine hydrate; diethylene glycol at 150℃; Reagens 4: Kaliumhydroxid;

2α-acetoxy-5α-spirostan-3-one (3001-32-9) → gitogenin (511-96-6)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride
Multi-step reaction with 2 steps 1.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.17 h / 20 °C 1.2: 0.5 h 2.1: sodium hydroxide / methanol; dichloromethane / 20 °C View Scheme

(25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside (39937-47-8) → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride; ethanol

ethanol (64-17-5) + sodium ethanolate (141-52-6) + (25R)-5α-Spirostan-2β,3β-diol (108814-79-5) → gitogenin (511-96-6)

Conditions	Yield
at 184℃;

(25R)-5α-Spirostan-2β,3β-diol (108814-79-5) → gitogenin (511-96-6)

Conditions	Yield
With ethanol; sodium ethanolate at 184℃;

Agaveside C → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 5h; Heating;	4 mg

gitogenin 3-O-β-D-glycopyranosyl(1->3)-β-D-glucopyranoside → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride for 5h;	57 mg

gitogenin 3-O-β-D-xylopyranosyl-(1-3)-<(β-D-xylopyranosyl)-(1-3)-β-D-glucopyranosyl-(1-2)>-β-D-glucopyranosyl-(1-4)-β-D-galactopyranoside → gitogenin (511-96-6)

Conditions	Yield
With sulfuric acid In ethanol for 2h; Heating;

gitogenin 3-O-{O-β-D-glucopyranosyl-(1->2)-O-[O-α-L-rhamnopyranosyl-(1->4)-β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside} → gitogenin (511-96-6)

Conditions	Yield
With sulfuric acid In ethanol for 2h; Heating;

gitogenin 3-O- (160067-92-5) → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;	7.3 mg

(25R)-2α,3β-dihydroxy-5α-spirostane 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 100℃; for 2h;	45 mg

(25R)-15-ethanediyldimercapto-2α,3β-bis-ethoxycarbonyloxy-5α-spirostan → gitogenin (511-96-6)

Conditions	Yield
With ethanol; nickel anschliessend Erwaermen mit aethanol. Kalilauge;

(25R)-2α,3β-diacetoxy-5α-spirostan-12-one → gitogenin (511-96-6)

Conditions	Yield
With ethanol; sodium ethanolate; hydrazine hydrate at 200℃;

(25R)-2α,3β-diacetoxy-5α-spirostan-15-one → gitogenin (511-96-6)

Conditions	Yield
With ethanol; hydrazine hydrate; diethylene glycol at 150℃; Reagens 4: Kaliumhydroxid;

(25R)-spirost-5-ene-2α,3β-diol → gitogenin (511-96-6)

Conditions	Yield
With diethyl ether; acetic acid; platinum Hydrogenation;
With ethanol; platinum Hydrogenation;

hydrogenchloride (7647-01-0) + (25R)-2α,3β,26-triacetoxy-5α-furost-20(22)-ene → gitogenin (511-96-6)

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + (25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside (39937-47-8) → gitogenin (511-96-6)

acrospirin → gitogenin (511-96-6)

Conditions	Yield
With hydrogenchloride; acetic acid

Upstream product

• 54191-26-3 26-O-β-D-glucopyranosyl-(25R)-5α-furostan-2α,3β,22α,26-tetraol 3-O-[β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)]-β-D-galactopyranoside 
• 16653-85-3 (25R)-5β-spirost-2-ene 
• 1499190-07-6 (25R)-26-[(β-D-glucopyranosyl)oxy]-2α,22α-dihydroxy-5α-furostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside 
• 1499187-77-7 (25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside 

Downstream Products

• 562-35-6 markogenin 

Relevant academic research and scientific papers

Cytotoxic triterpene and steroidal glycosides from the seeds of Digitalis purpurea and the synergistic cytotoxicity of steroidal glycosides and etoposide in SBC-3 cells

The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of s

Steroidal glycosides from the bulbs of Bessera elegans and their cytotoxic activities

Examination of the bulbs of Bessera elegans (Liliaceae) led to isolation of nine new and five known steroidal glycosides. The structures of the nine compounds were determined based on the results of spectroscopic analysis, including two-dimensional NMR, and hydrolysis followed by chromatographic and spectroscopic analysis. The isolated compounds and derivatives were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human diploid fibroblasts. One compound, the pseudo-furostanol glycoside, induced apoptosis in HL-60 and A549 cells in a time-dependent manner and cell-cycle arrest at the G0/G1 phase in A549 cells.

Steroidal glycosides of gitogenin from Allium rotundum

Two new steroidal glycosides were isolated by fractionation of total extracted substances from inflorescences and flower stalks of Allium rotundum (Alliaceae). The structures were determined on the basis of chemical transformations, physical constants, an