511-96-6

Basic information

• Product Name: (25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL
• Synonyms: GITOGENIN;DIGIN;(25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL;(25R)-2α,3β-Dihydroxy-5α-spirostan;(25R)-2α,3β-Dihydroxy-5α-spirostane;(2alpha,3beta,5alpha,25R)-Spirostan-2,3-diol;2alpha-Hydroxytigogenin;NSC 147752
• CAS NO: 511-96-6
• Molecular Formula: C₂₇H₄₄O₄
• Molecular Weight: 432.64
• Mol File: 511-96-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 272-273℃
• Boiling Point: 466.26°C (rough estimate)
• Flash Point: 276.9oC
• Appearance: /
• Density: 1.16
• Vapor Pressure: 1.22E-13mmHg at 25°C
• Refractive Index: 1.4840 (estimate)
• PKA: 14.62±0.70(Predicted)
• CAS DataBase Reference: (25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL(511-96-6)
• EPA Substance Registry System: (25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL(511-96-6)

Safety Data

• Hazardous Substances Data: 511-96-6(Hazardous Substances Data)

Usage

Uses

Gitogenin is isolated from a methanolic extract of the whole plant of Tribulus longipetalus which exhibits inhibitory activities against α-glucosidase, lipoxygenase, acetylcholinesterase and butyrylcholinesterase.

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 
• 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 
• 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 
• 16653-85-3 (25R)-5β-spirost-2-ene 

Downstream Products

• 562-35-6 markogenin 

Relevant articles and documents

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