Hocogenin

Base Information

• Chemical Name: Hocogenin
• CAS No.: 467-55-0
• Molecular Formula: C27H42O4
• Molecular Weight: 430.628
• NSC Number: 115921
• DSSTox Substance ID: DTXSID40859377
• Wikidata: Q105224985
• Mol file: 467-55-0.mol

Synonyms:3-Hydroxyspirostan-12-one;Hocogenin;(25r)-3b-hydroxy-5a-spirostan-12-one;16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one;NSC-115921;Spirostan-12-one, 3-hydroxy-, (3.beta.,5.alpha.,25R)-;SCHEMBL329539;3-Hydroxyspirostan-12-one #;DTXSID40859377;QOLRLLFJMZLYQJ-UHFFFAOYSA-N;(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one;NSC115921;AKOS032947793;5.alpha.-Spirostan-12-one, (25R)-;5.alpha.-Spirostan-12-one, 3.beta.-hydroxy-, (25R)-;2aS,2'R,4S,6aS,6bS,8aS,8bR,9S,11aS,12aS,12bR)-4-Hydroxy-5',6a,8a,9-tetramethylicosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-8(2H)-one;67-55-0

Chemical Property of Hocogenin

Chemical Property:

• Appearance/Colour: White solid.
• Vapor Pressure: 2.45E-14mmHg at 25°C
• Melting Point: 268 °C
• Refractive Index: 1.558
• Boiling Point: 548.9 °C at 760 mmHg
• PKA: 15.10±0.70(Predicted)
• Flash Point: 177.8 °C
• PSA: 55.76000
• Density: 1.16 g/cm³
• LogP: 4.97280
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 430.30830982
• Heavy Atom Count: 31
• Complexity: 766

Purity/Quality:

99% ^*data from raw suppliers

Hecogenin 90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(C(=O)CC5C4CCC6C5(CCC(C6)O)C)C)C)OC1
• Uses: antiinflammatory Hecogenin, is a sapogenin present in the leaves of species from the Agave genus, possessing wide spectrum of pharmacology activities, such as having antinociceptive properties.

Technology Process of Hocogenin

There total 47 articles about Hocogenin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

hecogenin acetate (915-35-5) → hecogenin (467-55-0)

Guidance literature:

With methanol; potassium hydroxide; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/np501033u

Reference yield: 79.0%

(2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-8(2H)-one → hecogenin (467-55-0)

Guidance literature:

With sodium perborate tetrahydrate; In tetrahydrofuran; water; for 3h;

DOI:10.1002/anie.201904028

Reference yield: 44.8%

α-D-glucopyranosyl(1->4)α-D-glucopyranosyl(1->4)α-D-glucopyranosyl(1->3)hecogenin → hecogenin (467-55-0)

Guidance literature:

With sulfuric acid;

DOI:10.1016/0031-9422(82)80059-9

upstream raw materials:

12-methylenetigogenin

3-oxo-5α-hecogenin

3β-acetoxy-(25R)-5α-spirostan-12-one

(25R)-12α-(Aminomethyl)-5α-spirostan-3β,12β-diol

Downstream raw materials:

hecogenin acetate

(25R)-12-oxo-5α-spirostan-3β-yl tosylate

(25R)-3β-hydroxy-5α-spirostan-12-one-(2,4-dinitro-phenylhydrazone)

3β,12β-dihydroxy-(25R)-5α-spirostane

Refernces

• 1、 Pettit, George R.,Moser, Bryan R.,Herald, Delbert L.,Knight, John C.,Chapuis, Jean-Charles,Zheng, Xing. "The cephalostatins. 23. Conversion of hecogenin to a steroidal 1,6-dioxaspiro[5.5]nonane analogue for cephalostatin 11". . p. 1067 - 1072. Retrieved 2015.
• 2、 Varshney, I. P.,Jain, D. C.,Srivastava, H. C.. "A TRIGLUCOSIDE OF HECOGENIN FROM FRUITS OF AGAVE CANTALA". . p. 239 - 240. Retrieved 1982.
• 3、 Wu, Jingjing,B?r, Robin M.,Guo, Lin,Noble, Adam,Aggarwal, Varinder K.. "Photoinduced Deoxygenative Borylations of Aliphatic Alcohols". supporting information. p. 18830 - 18834. Retrieved 2019/11/22.