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915-35-5

915-35-5

Identification

  • Product Name:Spirostan-12-one,3-(acetyloxy)-, (3b,5a,25R)-

  • CAS Number: 915-35-5

  • EINECS:

  • Molecular Weight:472.665

  • Molecular Formula: C29H44 O5

  • HS Code:

  • Mol File:915-35-5.mol

Synonyms:5a,25D-Spirostan-12-one, 3b-hydroxy-, acetate (6CI,7CI); 5a-Spirostan-12-one, 3b-hydroxy-, acetate, (25R)- (8CI);Spiro[8H-naphth[2',1':4,5]indeno[2,1-b]furan-8,2'-[2H]pyran], spirostan-12-onederiv.; 3b-Acetoxy-5a-spirostan-12-one; Hecogeninacetate; NSC 15489

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Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:Usbiological
  • Product Description:Hecogenin Acetate
  • Packaging:250mg
  • Price:$ 425
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:HecogeninAcetate,90%
  • Packaging:250mg
  • Price:$ 130
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Hecogenin Acetate >90.0%(GC)
  • Packaging:1g
  • Price:$ 56
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Hecogenin Acetate >90.0%(GC)
  • Packaging:5g
  • Price:$ 146
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Hecogenin acetate ≥90%
  • Packaging:25g
  • Price:$ 558
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:Hecogenin acetate
  • Packaging:100mg
  • Price:$ 80
  • Delivery:In stock
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  • Manufacture/Brand:Cayman Chemical
  • Product Description:Hecogenin Acetate ≥98%
  • Packaging:10g
  • Price:$ 245
  • Delivery:In stock
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  • Manufacture/Brand:Cayman Chemical
  • Product Description:Hecogenin Acetate ≥98%
  • Packaging:5g
  • Price:$ 135
  • Delivery:In stock
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  • Manufacture/Brand:Cayman Chemical
  • Product Description:Hecogenin Acetate ≥98%
  • Packaging:1g
  • Price:$ 49
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:HECOGENIN ACETATE 98.00%
  • Packaging:100G
  • Price:$ 2910.6
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Relevant articles and documentsAll total 4 Articles be found

-

Marker et al.

, (1947)

-

Effects of hecogenin and its possible mechanism of action on experimental models of gastric ulcer in mice

Santos Cerqueira, Gilberto,Dos Santos E Silva, Gabriela,Rios Vasconcelos, Emiliano,Fragoso De Freitas, Ana Paula,Arcanjo Moura, Brinell,Silveira MacEdo, Danielle,Lopes Souto, Augusto,Barbosa Filho, Jose Maria,De Almeida Leal, Luzia Kalyne,De Castro Brito, Gerly Anne,Souccar, Caden,De Barros Viana, Glauce Socorro

, p. 260 - 269 (2012)

This study investigates the gastroprotective effects of hecogenin, a steroid saponin isolated from Agave sisalana, on experimental models of gastric ulcer. Male Swiss mice were used in the models of ethanol- and indometacin-induced gastric ulcer. To clarify the hecogenin mechanism of action, the roles of nitric oxide (NO), sulfhydryls (GSH), K+ATP channels and prostaglandins were also investigated, and measurements of lipid peroxidation (TBARS assay) and nitrite levels in the stomach of hecogenin-treated and untreated animals were performed. Furthermore, the effects of hecogenin on myeloperoxidase (MPO) release from human neutrophils were assessed in vitro. Our results showed that hecogenin (3.1, 7.5, 15, 30, 60 and 90 mg/kg, p.o.) acutely administered, before ethanol or indomethacin, exhibited a potent gastroprotective effect. Although the pretreatments with L-NAME, an iNOS inhibitor, and capsazepine, a TRPV1 receptor agonist, were not able to reverse the hecogenin effect, this was reversed by glibenclamide, a K +ATP blocker, and indomethacin in the model of ethanol-induced gastric lesions. The hecogenin pretreatment normalized GSH levels and significantly reduced lipid peroxidation and nitrite levels in the stomach, as evaluated by the ethanol-induced gastric lesion model. The drug alone increased COX-2 expression and this effect was further enhanced in the presence of ethanol. It also decreased MPO release and significantly protected the gastric mucosa. In conclusion, we showed that hecogenin presents a significant gastroprotective effect that seems to be mediated by K +ATP channels opening and the COX-2/PG pathway. In addition, its antioxidant and anti-inflammatory properties may play a role in the gastroprotective drug effect.

Synthesis of betamethasone from the waste of Thai Agave sisalana

Kongkathip, Ngampong,Kongkathip, Boonsong,Noimai, Naratitt

, p. 865 - 874 (2007/10/03)

Synthesis of betamethasone from waste of Thai A. sisalana is described. Copyright Taylor & Francis Group, LLC.

Concurrent ring opening and halogenation of spiroketals

LaCour, Thomas G.,Fuchs

, p. 4655 - 4658 (2007/10/03)

Ring opening of various spiroketals with triphenylphosphine dihalides under neutral conditions produced ω-halo-enolethers in good to excellent yield. The method transformed even the very stable spiroketal of hecogenin acetate at temperatures below any previously reported for such isomerative opening.

TRANSFORMATIONS OF SOLASODINE AND DERIVATIVES OF HECOGENIN BY CUNNINGHAMELLA ELEGANS

Patel, Asmita V.,Blunden, Gerald,Crabb, Trevor A.

, p. 125 - 134 (2007/10/02)

Incubation of (25R)-5α-spirostane-3β,12β-diol (rickogenin) with the fungus Cunninghamella elegans led to the formation of (25R)-7β,12β-dihydroxy-5α-spirostan-3-one, (25R)-5α-spirostan-3β,7β,12β-triol and (25R)-5α-spirostan-3β,7α,12α-triol.Incubation of (25R)-5α-spirostan-3,12-dione (hecogenone) with the same fungus gave rise to (25R)-5α-spirostan-3,7,12-trione.When the (22R,25R)-spirosolane, solasod-5-en-3β-ol (solasodine) was incubated with C. elegans, solasod-5-ene-3β,7β-diol, solasod-5-ene-3β,7α-diol and 3β-hydroxysolasod-5-en-7-one were produced.In contrast, incubation of solasodine with Penicillium patulum gave solasod-4-en-3-one and the 6-methylsalicylic acid salt of solasodine.

Process route upstream and downstream products

Process route

acetic anhydride
108-24-7

acetic anhydride

hecogenin
467-55-0

hecogenin

hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
With pyridine; at 20 ℃;
95%
With pyridine; Ambient temperature;
With pyridine;
hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
With chromium(VI) oxide; acetic acid;
botogenin acetate
5996-01-0

botogenin acetate

hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
With diethyl ether; acetic acid; platinum; Hydrogenation;
cyclopseudohecogenin acetate
10005-61-5

cyclopseudohecogenin acetate

Acetic acid (2S,4aS,4bS,6aS,6bR,9aS,10aS,10bR,12aS)-8-((R)-4-iodo-3-methyl-butyl)-4a,6a,7-trimethyl-6-oxo-2,3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-2-yl ester
241465-96-3

Acetic acid (2S,4aS,4bS,6aS,6bR,9aS,10aS,10bR,12aS)-8-((R)-4-iodo-3-methyl-butyl)-4a,6a,7-trimethyl-6-oxo-2,3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-2-yl ester

Acetic acid (2S,4aS,4bS,6aS,6bR,9aS,10aS,10bR,12aS)-8-((R)-4-chloro-3-methyl-butyl)-4a,6a,7-trimethyl-6-oxo-2,3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-2-yl ester

Acetic acid (2S,4aS,4bS,6aS,6bR,9aS,10aS,10bR,12aS)-8-((R)-4-chloro-3-methyl-butyl)-4a,6a,7-trimethyl-6-oxo-2,3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-2-yl ester

hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
With 1H-imidazole; triphenylphospine diiodide; In dichloromethane; at 42 ℃; for 36h;
methanol
67-56-1

methanol

sodium methylate
124-41-4

sodium methylate

(25<i>R</i>)-3β,11α-diacetoxy-12β-methanesulfonyloxy-5α-spirostan

(25R)-3β,11α-diacetoxy-12β-methanesulfonyloxy-5α-spirostan

(25<i>R</i>)-3β-acetoxy-<i>C</i>-nor-5α-spirostan-11α-carbaldehyde

(25R)-3β-acetoxy-C-nor-5α-spirostan-11α-carbaldehyde

hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;
methanol
67-56-1

methanol

sodium methylate
124-41-4

sodium methylate

(25<i>R</i>)-3β,12β-diacetoxy-11α-methanesulfonyloxy-5α-spirostan

(25R)-3β,12β-diacetoxy-11α-methanesulfonyloxy-5α-spirostan

(25<i>R</i>)-3β-acetoxy-<i>C</i>-nor-5α-spirostan-11α-carbaldehyde

(25R)-3β-acetoxy-C-nor-5α-spirostan-11α-carbaldehyde

hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;
acetic acid
64-19-7,77671-22-8

acetic acid

(23<i>S</i>,25<i>R</i>)-3β,11β-diacetoxy-23-bromo-5α-spirostan-12-one
121009-65-2

(23S,25R)-3β,11β-diacetoxy-23-bromo-5α-spirostan-12-one

hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
acetic anhydride
108-24-7

acetic anhydride

hecogenin
467-55-0

hecogenin

hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
With pyridine; at 20 ℃;
95%
With pyridine; Ambient temperature;
With pyridine;
hecogenin acetate
915-35-5

hecogenin acetate

Conditions
Conditions Yield
With chromium(VI) oxide; acetic acid;

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