126-17-0,MFCD00037844
Catalog No.:AA000QLF

126-17-0 | Spirosol-5-en-3-ol, (3β,22α,25R)-

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Purity
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Price(USD)
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1mg
98%
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$15.00   $11.00
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10mg
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$49.00   $34.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA000QLF
Chemical Name:
Spirosol-5-en-3-ol, (3β,22α,25R)-
CAS Number:
126-17-0
Molecular Formula:
C27H45NO
Molecular Weight:
399.6523
MDL Number:
MFCD00037844
SMILES:
C[C@@H]1CC[C@@]2(NC1)O[C@@H]1[C@H]([C@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC[C@@H]3[C@]([C@H]1CC2)(C)CCCC3)C
Properties
Computed Properties
 
Complexity:
749  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
11  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
5.4  

Downstream Synthesis Route

[1]JournaloftheChemicalSociety,1952,p.3587,3589

[2]JournaloftheChemicalSociety,1958,p.1419,1420,1421

[3]ChemistryofNaturalCompounds,1972,vol.8,p.138    KhimiyaPrirodnykhSoedinenii,1972,vol.8,p.132-133

[1]ArchivderPharmazie,1939,vol.277,p.329,336    ArchivderPharmazie(Weinheim,Germany),1937,vol.275,p.336,342

[2]Proceedings-IndianAcademyofSciences,SectionA,1936,p.255,258

[3]GazzettaChimicaItaliana,1911,vol.41,p.I534,545,546

[4]ChemistryofNaturalCompounds,1973,vol.9,p.659    KhimiyaPrirodnykhSoedinenii,1973,vol.9,p.682-683

[1]GazzettaChimicaItaliana,1914,vol.44,p.II191,197

[1]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn12

[2]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn11;27;29;31

[3]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn12

[4]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn12

[5]Bite;Tuzson[ActaChimicaAcademiaeScientiarumHungaricae,1958,vol.17,p.241,247]Satoetal.[JournalofOrganicChemistry,1959,vol.24,p.893][ZhurnalObshcheiKhimii,1960,vol.25,p.783,785]Suworowetal.[ZhurnalObshcheiKhimii,1959,vol.29,p.329,331;engl.Aug.S.333,335]Magyaretal.[ActaChimicaAcademiaeScientiarumHungaricae,1958,vol.17,p.249,251]Sato;Ikekawa[JournalofOrganicChemistry,1960,vol.25,p.786,788]

[1]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn13

Literature

Title: Solasodine inhibits invasion of human lung cancer cell through downregulation of miR-21 and MMPs expression.

Journal: Chemico-biological interactions 20170425

Title: Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate.

Journal: Steroids 20120901

Title: Solasodine rhamnosyl glycosides cause apoptosis in cancer cells. Do they also prime the immune system resulting in long-term protection against cancer?

Journal: Planta medica 20120301

Title: Synthesis of solasodine glycoside derivatives and evaluation of their cytotoxic effects on human cancer cells.

Journal: Drug discoveries & therapeutics 20120201

Title: Effects of auxins on the production of steroidal alkaloids in rapidly proliferating tissue and cell cultures of Solanum lyratum.

Journal: Phytochemical analysis : PCA 20120101

Title: Conversion of spirostane and solanidane into pregnane (1)introduction of oxygen function into C-23.

Journal: Chemical & pharmaceutical bulletin 20120101

Title: In situ RBL receptor visualization and its mediated anticancer activity for solasodine rhamnosides.

Journal: Chembiochem : a European journal of chemical biology 20111104

Title: Anti-inflammatory activity of an alkaloid from Solanum trilobatum on acute and chronic inflammation models.

Journal: Natural product research 20110701

Title: The naturally occurring steroid solasodine induces neurogenesis in vitro and in vivo.

Journal: Neuroscience 20110602

Title: Technology of compact MAb and its application for medicinal plant breeding named as missile type molecular breeding.

Journal: Current drug discovery technologies 20110301

Title: Anticonvulsant activity of solasodine isolated from Solanum sisymbriifolium fruits in rodents.

Journal: Pharmaceutical biology 20110201

Title: Elucidation of the mass fragmentation pathways of potato glycoalkaloids and aglycons using Orbitrap mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20100901

Title: Antinociceptive activity of steroid alkaloids isolated from Solanum trilobatum Linn.

Journal: Journal of Asian natural products research 20100801

Title: Sequential injection analysis with lab-at-valve (SI-LAV) for the determination of solasodine in Solanum species.

Journal: Talanta 20100415

Title: Biological activity of alkaloids from Solanum dulcamara L.

Journal: Natural product research 20090101

Title: Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages.

Journal: FEBS letters 20080709

Title: [Induction and in vitro culture of hairy roots of Solanum nigrum L. var. pauciflorum Liou and its solasodine production].

Journal: Fen zi xi bao sheng wu xue bao = Journal of molecular cell biology 20080601

Title: Solasodine glycoalkaloids: a novel topical therapy for basal cell carcinoma. A double-blind, randomized, placebo-controlled, parallel group, multicenter study.

Journal: International journal of dermatology 20080101

Title: Salinity stress enhances production of solasodine in Solanum nigrum L.

Journal: Chemical & pharmaceutical bulletin 20080101

Title: Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants.

Journal: Methods in molecular biology (Clifton, N.J.) 20080101

Title: Diosgenin, a naturally occurring steroid, suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt, mTOR and JNK phosphorylation.

Journal: FEBS letters 20071222

Title: Efficient synthesis of solasodine, O-acetylsolasodine, and soladulcidine as anticancer steroidal alkaloids.

Journal: Chemistry & biodiversity 20070101

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: A validated liquid chromatographic method for estimation of solasodine in various Solanum species and market formulations.

Journal: Journal of AOAC International 20060101

Title: Impaired female sexual behavior of rat offspring exposed to Solanum lycocarpum unripe fruits during gestation and lactation: lack of hormonal and fertility alterations.

Journal: Pharmacology, biochemistry, and behavior 20050801

Title: Liquid-liquid systems for acid hydrolysis of glycoalkaloids from Solanum tuberosum L. tuber sprouts and solanidine extraction.

Journal: Medical science monitor : international medical journal of experimental and clinical research 20050701

Title: [The preparation and quality control of Solanum lyratum Thunb Extract gel].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20050701

Title: Production of solasodine by Solanum laciniatum using plant tissue culture technique.

Journal: Indian journal of experimental biology 20041001

Title: Potato glycoalkaloids: true safety or false sense of security?

Journal: Trends in biotechnology 20040301

Title: Anti-solasodine glycoside single-chain Fv antibody stimulates biosynthesis of solasodine glycoside in plants.

Journal: Plant cell reports 20031201

Title: Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030101

Title: Evidence for essential histidine and dicarboxylic amino-acid residues in the active site of UDP-glucose : solasodine glucosyltransferase from eggplant leaves.

Journal: Acta biochimica Polonica 20030101

Title: Effects of short-term treatment of solasodine on cauda epididymis in dogs.

Journal: Indian journal of experimental biology 20020201

Title: Phospholipids modulate the substrate specificity of soluble UDP-glucose:steroid glucosyltransferase from eggplant leaves.

Journal: Phytochemistry 20011101

Title: Isolation of solasodine and other steroidal alkaloids and sapogenins by direct hydrolysis-extraction of Solanum plants or glycosides therefrom.

Journal: Phytochemistry 20011001

Title: Effects of naturally occurring glucosides, solasodine glucosides, ginsenosides and parishin derivatives on multidrug resistance of lymphoma cells and leukocyte functions.

Journal: In vivo (Athens, Greece) 20010101

Title: Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells.

Journal: Anticancer research 20010101

Title: Lecanu L, et al. The naturally occurring steroid solasodine induces neurogenesis in vitro and in vivo. Neuroscience. 2011 Jun 2;183:251-64.

Title: Chauhan K, et al. Anticonvulsant activity of solasodine isolated from Solanum sisymbriifolium fruits in rodents. Pharm Biol. 2011 Feb;49(2):194-9.

Title: Akhtar S, et al. Evaluation and Elucidation Studies of Natural Aglycones for Anticancer Potential using Apoptosis-Related Markers: An In silico Study. Interdiscip Sci. 2018 Jun;10(2):297-310.

Title: Gupta RS, et al. Effects of short-term treatment of solasodine on cauda epididymis in dogs. Indian J Exp Biol. 2002 Feb;40(2):169-73.

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SDS
Related Products of 126-17-0
Tags:126-17-0 Molecular Formula|126-17-0 MDL|126-17-0 SMILES|126-17-0 Spirosol-5-en-3-ol, (3β,22α,25R)-
Catalog No.: AA000QLF
126-17-0,MFCD00037844
126-17-0 | Spirosol-5-en-3-ol, (3β,22α,25R)-
Pack Size: 1mg
Purity: 98%
in stock
$15.00 $11.00
Pack Size: 10mg
Purity: 98%
in stock
$49.00 $34.00
Quantity
- +
Add to Card
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Technical Information
Catalog Number: AA000QLF
Chemical Name: Spirosol-5-en-3-ol, (3β,22α,25R)-
CAS Number: 126-17-0
Molecular Formula: C27H45NO
Molecular Weight: 399.6523
MDL Number: MFCD00037844
SMILES: C[C@@H]1CC[C@@]2(NC1)O[C@@H]1[C@H]([C@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC[C@@H]3[C@]([C@H]1CC2)(C)CCCC3)C
Properties
Complexity: 749  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 11  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 30  
Hydrogen Bond Acceptor Count: 3  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 5.4  
Downstream Synthesis Route
20311-51-7    126-17-0 

[1]JournaloftheChemicalSociety,1952,p.3587,3589

[2]JournaloftheChemicalSociety,1958,p.1419,1420,1421

[3]ChemistryofNaturalCompounds,1972,vol.8,p.138    KhimiyaPrirodnykhSoedinenii,1972,vol.8,p.132-133

19121-58-5    126-17-0 

[1]ArchivderPharmazie,1939,vol.277,p.329,336    ArchivderPharmazie(Weinheim,Germany),1937,vol.275,p.336,342

[2]Proceedings-IndianAcademyofSciences,SectionA,1936,p.255,258

[3]GazzettaChimicaItaliana,1911,vol.41,p.I534,545,546

[4]ChemistryofNaturalCompounds,1973,vol.9,p.659    KhimiyaPrirodnykhSoedinenii,1973,vol.9,p.682-683

19121-58-5    126-17-0    3669-17-8 

[1]GazzettaChimicaItaliana,1914,vol.44,p.II191,197

108-24-7    126-17-0    979-02-2 

[1]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn12

[2]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn11;27;29;31

[3]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn12

[4]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn12

[5]Bite;Tuzson[ActaChimicaAcademiaeScientiarumHungaricae,1958,vol.17,p.241,247]Satoetal.[JournalofOrganicChemistry,1959,vol.24,p.893][ZhurnalObshcheiKhimii,1960,vol.25,p.783,785]Suworowetal.[ZhurnalObshcheiKhimii,1959,vol.29,p.329,331;engl.Aug.S.333,335]Magyaretal.[ActaChimicaAcademiaeScientiarumHungaricae,1958,vol.17,p.249,251]Sato;Ikekawa[JournalofOrganicChemistry,1960,vol.25,p.786,788]

64-19-7    126-17-0    979-02-2 

[1]CurrentPatentAssignee:C.H.BoehringerSohnAG&Co.KG-EP1359154,2003,A1Locationinpatent:Page/Pagecolumn13

Literature fold

Title: Solasodine inhibits invasion of human lung cancer cell through downregulation of miR-21 and MMPs expression.

Journal: Chemico-biological interactions20170425

Title: Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate.

Journal: Steroids20120901

Title: Solasodine rhamnosyl glycosides cause apoptosis in cancer cells. Do they also prime the immune system resulting in long-term protection against cancer?

Journal: Planta medica20120301

Title: Synthesis of solasodine glycoside derivatives and evaluation of their cytotoxic effects on human cancer cells.

Journal: Drug discoveries & therapeutics20120201

Title: Effects of auxins on the production of steroidal alkaloids in rapidly proliferating tissue and cell cultures of Solanum lyratum.

Journal: Phytochemical analysis : PCA20120101

Title: Conversion of spirostane and solanidane into pregnane (1)introduction of oxygen function into C-23.

Journal: Chemical & pharmaceutical bulletin20120101

Title: In situ RBL receptor visualization and its mediated anticancer activity for solasodine rhamnosides.

Journal: Chembiochem : a European journal of chemical biology20111104

Title: Anti-inflammatory activity of an alkaloid from Solanum trilobatum on acute and chronic inflammation models.

Journal: Natural product research20110701

Title: The naturally occurring steroid solasodine induces neurogenesis in vitro and in vivo.

Journal: Neuroscience20110602

Title: Technology of compact MAb and its application for medicinal plant breeding named as missile type molecular breeding.

Journal: Current drug discovery technologies20110301

Title: Anticonvulsant activity of solasodine isolated from Solanum sisymbriifolium fruits in rodents.

Journal: Pharmaceutical biology20110201

Title: Elucidation of the mass fragmentation pathways of potato glycoalkaloids and aglycons using Orbitrap mass spectrometry.

Journal: Journal of mass spectrometry : JMS20100901

Title: Antinociceptive activity of steroid alkaloids isolated from Solanum trilobatum Linn.

Journal: Journal of Asian natural products research20100801

Title: Sequential injection analysis with lab-at-valve (SI-LAV) for the determination of solasodine in Solanum species.

Journal: Talanta20100415

Title: Biological activity of alkaloids from Solanum dulcamara L.

Journal: Natural product research20090101

Title: Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages.

Journal: FEBS letters20080709

Title: [Induction and in vitro culture of hairy roots of Solanum nigrum L. var. pauciflorum Liou and its solasodine production].

Journal: Fen zi xi bao sheng wu xue bao = Journal of molecular cell biology20080601

Title: Solasodine glycoalkaloids: a novel topical therapy for basal cell carcinoma. A double-blind, randomized, placebo-controlled, parallel group, multicenter study.

Journal: International journal of dermatology20080101

Title: Salinity stress enhances production of solasodine in Solanum nigrum L.

Journal: Chemical & pharmaceutical bulletin20080101

Title: Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants.

Journal: Methods in molecular biology (Clifton, N.J.)20080101

Title: Diosgenin, a naturally occurring steroid, suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt, mTOR and JNK phosphorylation.

Journal: FEBS letters20071222

Title: Efficient synthesis of solasodine, O-acetylsolasodine, and soladulcidine as anticancer steroidal alkaloids.

Journal: Chemistry & biodiversity20070101

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology20060501

Title: A validated liquid chromatographic method for estimation of solasodine in various Solanum species and market formulations.

Journal: Journal of AOAC International20060101

Title: Impaired female sexual behavior of rat offspring exposed to Solanum lycocarpum unripe fruits during gestation and lactation: lack of hormonal and fertility alterations.

Journal: Pharmacology, biochemistry, and behavior20050801

Title: Liquid-liquid systems for acid hydrolysis of glycoalkaloids from Solanum tuberosum L. tuber sprouts and solanidine extraction.

Journal: Medical science monitor : international medical journal of experimental and clinical research20050701

Title: [The preparation and quality control of Solanum lyratum Thunb Extract gel].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20050701

Title: Production of solasodine by Solanum laciniatum using plant tissue culture technique.

Journal: Indian journal of experimental biology20041001

Title: Potato glycoalkaloids: true safety or false sense of security?

Journal: Trends in biotechnology20040301

Title: Anti-solasodine glycoside single-chain Fv antibody stimulates biosynthesis of solasodine glycoside in plants.

Journal: Plant cell reports20031201

Title: Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association20030101

Title: Evidence for essential histidine and dicarboxylic amino-acid residues in the active site of UDP-glucose : solasodine glucosyltransferase from eggplant leaves.

Journal: Acta biochimica Polonica20030101

Title: Effects of short-term treatment of solasodine on cauda epididymis in dogs.

Journal: Indian journal of experimental biology20020201

Title: Phospholipids modulate the substrate specificity of soluble UDP-glucose:steroid glucosyltransferase from eggplant leaves.

Journal: Phytochemistry20011101

Title: Isolation of solasodine and other steroidal alkaloids and sapogenins by direct hydrolysis-extraction of Solanum plants or glycosides therefrom.

Journal: Phytochemistry20011001

Title: Effects of naturally occurring glucosides, solasodine glucosides, ginsenosides and parishin derivatives on multidrug resistance of lymphoma cells and leukocyte functions.

Journal: In vivo (Athens, Greece)20010101

Title: Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells.

Journal: Anticancer research20010101

Title: Lecanu L, et al. The naturally occurring steroid solasodine induces neurogenesis in vitro and in vivo. Neuroscience. 2011 Jun 2;183:251-64.

Title: Chauhan K, et al. Anticonvulsant activity of solasodine isolated from Solanum sisymbriifolium fruits in rodents. Pharm Biol. 2011 Feb;49(2):194-9.

Title: Akhtar S, et al. Evaluation and Elucidation Studies of Natural Aglycones for Anticancer Potential using Apoptosis-Related Markers: An In silico Study. Interdiscip Sci. 2018 Jun;10(2):297-310.

Title: Gupta RS, et al. Effects of short-term treatment of solasodine on cauda epididymis in dogs. Indian J Exp Biol. 2002 Feb;40(2):169-73.

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