56786-63-1

Basic information

• Product Name: Spirostan-6-one, 3,5-dihydroxy-, (3b,5a,25R)-
• Synonyms: Spirostan-6-one, 3,5-dihydroxy-, (3b,5a,25R)-;5a-hydroxy laxogenin;DI 31;Brassinosteroid BB 16;Biobras 16;BB 16;(3beta,5alpha,25R)-3,5-Dihydroxyspirostan-6-one;(2AR,2'R,4S,5'R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-2a,4-dihydroxy-5',6a,8a,9-tetramethylicosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-2(11aH)-one
• CAS NO: 56786-63-1
• Molecular Formula: C₂₇H₄₂O₅
• Molecular Weight: 446.619
• EINECS: 1312995-182-4
• Mol File: 56786-63-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 247-250 °C
• Boiling Point: 578.4±50.0 °C(Predicted)
• Appearance: White or off-white powder
• Density: 1.21±0.1 g/cm3 (20 oC 760 Torr)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.62±0.70(Predicted)
• CAS DataBase Reference: Spirostan-6-one, 3,5-dihydroxy-, (3b,5a,25R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Spirostan-6-one, 3,5-dihydroxy-, (3b,5a,25R)-(56786-63-1)
• EPA Substance Registry System: Spirostan-6-one, 3,5-dihydroxy-, (3b,5a,25R)-(56786-63-1)

Safety Data

• Hazardous Substances Data: 56786-63-1(Hazardous Substances Data)

Usage

Uses

5α-Hydroxy laxogenin is a synthetic derivative of a naturally occurring spirostane-type steroid, laxogenin.?It is a synthetic spirostane-type steroid, which is contained in dietary supplements and advertised as anabolic agent.

Description

5α-hydroxy Laxogenin is a brassinosteroid analog and a derivative of diosgenin.Topical administration of 5α-hydroxy laxogenin (4, 8, and 12 ppm), in combination with a commercial fertilizer, increases the yield and fresh weight of endives (C. endivia).It also inhibits sodium chloride-induced decreases in the fresh weight of lettuce shoots and roots when applied topically at concentrations of 0.1 and 1 μM, as well as inhibits increases in ethylene emission at a concentration of 1 μM.

Synthetic route

(25R)-3α,5-cyclo-5α-spirostan-6-one (127128-79-4) → (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1)

Conditions	Yield
With acetic acid for 2h; Heating;	98%

(25R)-3β-acetoxy-5-hydroxy-5α-spirostan-6-one (5874-17-9) → (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 3h; Reflux;	95%

(25R)-spirostan-22α-O-3β,5α,6β-triol (56816-69-4) → (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1)

Conditions	Yield
With N-Bromosuccinimide In 1,4-dioxane; water at 20℃; for 2h; Darkness;	83%
Multi-step reaction with 3 steps 1: 84 percent / imidazole / dimethylformamide / 3 h 2: PCC / CH2Cl2 / 0 - 20 °C 3: 7.14 g / TBFA / tetrahydrofuran / 6 h View Scheme

C33H56O5Si → (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1)

Conditions	Yield
With TBFA In tetrahydrofuran for 6h;	7.14 g

(25R)-3β-(t-butyldimethylsilyloxy)-5α-spirostane-5,6β-diol (876908-18-8) → (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: PCC / CH2Cl2 / 0 - 20 °C 2: 7.14 g / TBFA / tetrahydrofuran / 6 h View Scheme

5,6-epoxyspirostane → (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: perchloric acid / water; tetrahydrofuran / 3 h / 20 °C 2: N-Bromosuccinimide / water; 1,4-dioxane / 2 h / 20 °C / Darkness View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) + 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (149707-75-5) → 5α-hydroxylaxogenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (1373440-75-5)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere; Molecular sieve;	94%

p-toluenesulfonyl chloride (98-59-9) + (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-6-oxo-3β-(p-toluenesulfonyloxy)-5α-spirostane

Conditions	Yield
With pyridine at 20℃; for 24h;	88%
With pyridine at 20℃; for 24h;
With pyridine at 20℃;
With pyridine

O-carboxymethylhydroxylamine hydrochloride (20295-82-3) + (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-6E-[O-(carboxymethyl)oximino]-5-hydroxy-5α-spirostan-3β-ol

Conditions	Yield
With pyridine at 20℃;	88%

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-5α-hydroxy-5α-spirosta-3,6-dione (74395-54-3)

Conditions	Yield
With Jones reagent In water; acetone at 20℃;	81.5%

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-3β,5-dihydroxy-5β-spirostan-6-one (876908-20-2)

Conditions	Yield
With potassium hydroxide In methanol for 24h; Heating;	74%

phenyl isocyanate (103-71-9) + (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-5α-hydroxy-6-oxo-spirostan-3β-yl phenylcarbamate

Conditions	Yield
With hydrogenchloride In chloroform; water for 24h; Reflux;	68%

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) + methyl iodide (74-88-4) → 6β-methyl-5α-(25R)-spirostane-3β,5,6α-triol (83110-94-5)

Conditions	Yield
With magnesium 1.) ether, 2.) THF, 3 h, reflux; Yield given. Multistep reaction;

formic acid (64-18-6) + (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → C28H42O6

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 24h; Mitsunobu reaction;

methanesulfonic acid (75-75-2) + (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → C28H44O7S

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 40℃; for 24h; Mitsunobu reaction;
With dmap; di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 48.25h; Mitsunobu reaction; Inert atmosphere;

acetic anhydride (108-24-7) + (25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-3β-acetoxy-5-hydroxy-5α-spirostan-6-one (5874-17-9)

Conditions	Yield
With pyridine at 20℃;

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → C27H40O5 (325125-66-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: 2.03 g / Jones reagent / acetone / 2 h / Heating View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → C27H42O5

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 20 °C 2: 2.03 g / Jones reagent / acetone / 2 h / Heating 3: H2 / Pd/C / ethanol / 24 h View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-5,6-seco-A-homo-5(10)-oxa-5-oxo-spirostan-6-oic acid (909879-88-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 20 °C 2: 2.03 g / Jones reagent / acetone / 2 h / Heating 3: H2 / Pd/C / ethanol / 24 h 4: 1.54 g / mCPBA / CH2Cl2 / 20 °C View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → C47H69N3O12

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / 20 °C 2: 2.03 g / Jones reagent / acetone / 2 h / Heating 3: H2 / Pd/C / ethanol / 24 h 4: 1.54 g / mCPBA / CH2Cl2 / 20 °C 5: 1.1 g / methanol / 20 °C View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-5-hydroxy-5α-spirostan-6-one (321857-67-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / pyridine / 24 h / 20 °C 2: 90 percent / LiBr; Li2CO3 / dimethylformamide / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine / 24 h / 20 °C 2: 2.29 g / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-2α,3α,5-trihydroxy-5α-spirostan-6-one

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / pyridine / 24 h / 20 °C 2: 90 percent / LiBr; Li2CO3 / dimethylformamide / 1 h / Heating 3: 91 percent / OsO4 / N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 24 h / 20 °C View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-3β-amino-5-hydroxy-5α-spirostan-6-one

Conditions	Yield
Multi-step reaction with 3 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 40 °C 2: 595 mg / NaN3 / various solvent(s) / 48 h / 50 °C 3: H2 / Lindlar catalyst / ethanol / 36 h View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-3β-amino-5-hydroxy-5β-spirostan-6-one

Conditions	Yield
Multi-step reaction with 6 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 40 °C 2: 595 mg / NaN3 / various solvent(s) / 48 h / 50 °C 3: H2 / Lindlar catalyst / ethanol / 36 h 4: 620 mg / Et3N / dioxane / 20 h 5: KOH / methanol / 24 h / Heating 6: 313 mg / CF3CO2H / CH2Cl2 / 0.17 h View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-2β,3β-epoxy-5-hydroxy-5β-spirostan-6-one (876908-24-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / KOH / methanol / 24 h / Heating 2: pyridine / 24 h / 20 °C 3: 2.36 g / Li2CO3; LiBr / dimethylformamide / 2 h / Heating 4: 48 percent / mCPBA / CH2Cl2 / 0 - 20 °C View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-2α,3α-epoxy-5-hydroxy-5β-spirostan-6-one (876908-23-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / KOH / methanol / 24 h / Heating 2: pyridine / 24 h / 20 °C 3: 2.36 g / Li2CO3; LiBr / dimethylformamide / 2 h / Heating 4: 24 percent / mCPBA / CH2Cl2 / 0 - 20 °C View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-3α,5-dihydroxy-5α-spirostan-6-one (876908-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 20 °C 2: 800 mg / NaHCO3 / methanol; H2O / 1 h / 20 °C View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-3α,5-dihydroxy-5β-spirostan-6-one

Conditions	Yield
Multi-step reaction with 3 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 20 °C 2: 800 mg / NaHCO3 / methanol; H2O / 1 h / 20 °C 3: 71 percent / KOH / methanol / 24 h / Heating View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-3β-azido-5-hydroxy-5α-spirostan-6-one (876908-28-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Ph3P; DIAD / tetrahydrofuran / 24 h / 40 °C 2: 595 mg / NaN3 / various solvent(s) / 48 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: dmap; di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48.25 h / 20 °C / Inert atmosphere 2: sodium azide / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 48 h / 20 °C / Inert atmosphere View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-2β,3β,5-trihydroxy-5α-spirostan-6-one (705941-87-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: pyridine / 24 h / 20 °C 2.1: 2.29 g / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating 3.1: AcOAg; I2 / acetic acid; H2O / 3 h / Heating 3.2: 61 percent / KOH / methanol / 0.5 h / Heating View Scheme

(25R)-3β,5-dihydroxy-5α-spirostan-6-one (56786-63-1) → (25R)-2β,3β,5-trihydroxy-5β-spirostan-6-one (876908-22-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / KOH / methanol / 24 h / Heating 2: pyridine / 24 h / 20 °C 3: 2.36 g / Li2CO3; LiBr / dimethylformamide / 2 h / Heating 4: 68 percent / NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 24 h / 20 °C View Scheme

Upstream product

• 5874-17-9 (25R)-3β-acetoxy-5-hydroxy-5α-spirostan-6-one 
• 876908-18-8 (25R)-3β-(t-butyldimethylsilyloxy)-5α-spirostane-5,6β-diol 
• 127128-79-4 (25R)-3α,5-cyclo-5α-spirostan-6-one 
• 56816-69-4 (25R)-spirostan-22α-O-3β,5α,6β-triol 

Downstream Products

• 1373440-75-5 5α-hydroxylaxogenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 1373440-86-8 5α-hydroxylaxogenyl 4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside 
• 1373440-84-6 C₄₀H₅₆O₁₀ 
• 115332-88-2 Anzurogenin A 
• 876908-22-4 (25R)-2β,3β,5-trihydroxy-5β-spirostan-6-one 
• 705941-87-3 (25R)-2β,3β,5-trihydroxy-5α-spirostan-6-one 
• 325125-66-4 C₂₇H₄₀O₅ 
• 5874-17-9 (25R)-3β-acetoxy-5-hydroxy-5α-spirostan-6-one 
• 51092-15-0 (25R)-5α-spirostan-6-one-2α,3α-diol 

Relevant articles and documents

In vitro neuroprotective and anti-inflammatory activities of natural and semi-synthetic spirosteroid analogues

Two spirosteroid analogues were synthesized and evaluated for their in vitro neuroprotective activities in PC12 cells, against glutamate-induced excitotoxicity and mitochondrial damage in glucose deprivation conditions, as well as their anti-inflammatory potential in LPS/IFNγ-stimulated microglia primary cultures. We also evaluated the in vitro anti-excitotoxic and anti-inflammatory activities of natural and endogenous steroids. Our results show that the plant-derived steroid solasodine decreased PC12 glutamate-induced excitotoxicity, but not the cell death induced by mitochondrial damage and glucose deprivation. Among the two synthetic spirosteroid analogues, only the (25R)-5α-spirostan-3,6-one (S15) protected PC12 against ischemia-related in vitro models and inhibited NO production, as well as the release of IL-1β by stimulated primary microglia. These findings provide further insights into the role of specific modifications of the A and B rings of sapogenins for their neuroprotective potential.

The preparation of the spirostanic analogues of brassinolide and castasterone

Methods for the preparation of the spirostanic analogues of brassinosteroids (25R)-5α-spirostan-6-one-2α,3α-diol and (25R)-B-homo-5α-spirostan-6-oxo-7-oxalactone-2α,3α-diol, starting from diosgenin, were examined. The best preparative route was via diosgenin tosylation, isosteroidal rearrangement with potassium acetate in aqueous acetone, oxidation with Jones reagent, cyclopropyl ring opening with hydrobromic acid, hydrogen bromide elimination with lithium bromide and carbonate, dihydroxylation with osmium tetroxide and N-methylmorpholine N-oxide, producing (25R)-5α-spirostan-6-one-2α,3α-diol in 57.3% overall yield and lactonization with trifluoroperoxyacetic acid producing (25R)-B-homo-5α-spirostan-6-oxo-7-oxalactone-2α,3α-diol in 24.6% overall yield from diosgenin. The shortest route to (25R)-5α-spirostan-6-one-2α,3α-diol results in only 39.4% overall yield.