(3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-6,9,14-triol

Base Information

• Chemical Name: (3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-6,9,14-triol
• CAS No.: 84605-18-5
• Molecular Formula: C30H50O5
• Molecular Weight: 490.724
• Hs Code.: 2942000000
• European Community (EC) Number: 846-798-1
• Wikipedia: Cycloastragenol
• Mol file: 84605-18-5.mol

Synonyms:astramembrangenin;cycloastragenol;cyclogalegigenin;GRN510

Chemical Property of (3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-6,9,14-triol

Chemical Property:

• Appearance/Colour: Colorless needle crystal
• Vapor Pressure: 8.17E-18mmHg at 25°C
• Refractive Index: 1.582
• Boiling Point: 617.2 °C at 760 mmHg
• PKA: 14.57±0.29(Predicted)
• Flash Point: 327.1 °C
• PSA: 90.15000
• Density: 1.2 g/cm³
• LogP: 4.43660
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Pyridine (Slightly)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 490.36582469
• Heavy Atom Count: 35
• Complexity: 916

Purity/Quality:

98%, ^*data from raw suppliers

Cycloastragenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(CCC23C1C(CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)O)O)C
• Isomeric SMILES: C[C@]12CCC34C[C@@]35CC[C@@H](C([C@@H]5[C@H](C[C@H]4[C@@]1(C[C@@H]([C@@H]2[C@@]6(CC[C@@H](O6)C(C)(C)O)C)O)C)O)(C)C)O
• Recent ClinicalTrials: Telomerase Activator and Retinal Amyloid
• Description: Cycloastragenol (TA-65), a small-triterpenoid purified from the root of an Asian medicinal herb, has currently received particular attention for its potential to regulate transcription of telomerase. TA-65 is capable to increase average telomere length and to decrease the percentage of critically short telomeres and DNA damage in MEFs that harbor critically short telomeres. The effects on telomerase appear to be in common with other triterpenoid saponins (ie, ginsenosides RG1 and Rg3). These compounds at concentrations from 1 to 20 μM were reported to protect against IL-1β-, H2O2-, and tert-butylhydroperoxide-induced senescence in human chondrocytes, endothelial progenitor cells and fibroblasts, respectively.
• Uses: Cycloastragenol is an aglycone derivative of astragaloside IV found in the root of Korean Astragalus membranaceus.

Technology Process of (3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-6,9,14-triol

There total 57 articles about (3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-6,9,14-triol 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: 64.0%

astragaloside IV (83207-58-3,84687-43-4) → cycloastragenol (84605-18-5,90865-25-1,104112-00-7,78574-94-4)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 168h;

Reference yield: 4.0%

astragaloside IV (83207-58-3,84687-43-4) → 20R,24S-epoxy-3β,16β,25-trihydroxy-9β-methyl-19-norlanost-1,5-diene + cycloastragenol (84605-18-5,90865-25-1,104112-00-7,78574-94-4) + cyclosieversigenin 3-O-β-D-xylopyranoside (86541-83-5) + cyclosieversigenin 6-O-β-D-glucopyranoside (86764-12-7)

Guidance literature:

With sulfuric acid; In methanol; for 1.5h; Reflux;

Reference yield:

20S,24R-epoxycycloartan-3,6,16,25-tetraol-3-O-β-D-(2'-O-acetyl)xylopyranosyl-6-O-β-D-xylopyranoside (84883-00-1) → D-xylose (58-86-6) + 20(S),24(R)-epoxy-9β,19-cyclolanostan-3β,6α,16β,25-tetrol (84605-18-5)

Guidance literature:

Acidic conditions;

DOI:10.1007/s10600-012-0424-9

upstream raw materials:

Cycloaraloside A

cyclocarposide

cycloaraloside E

Cycloaraloside F

Downstream raw materials:

astragaloside III

2-(L)-amino-3-phenyl-propionic acid 6α,16β-dihydroxy-17-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydrofuran-2-yl]-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3α-yl ester hydrochloride

2-(L)-amino-3-phenyl-propionic acid 3β,16β-dihydroxy-17-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-6α-yl ester hydrochloride

C₄₄H₆₇NO₈

Refernces

• 1、 Alaniya,Chkadua,Gigoshvili,Kemertelidze. "Cycloascauloside a from Astragalus caucasicus leaves". . p. 445 - 448. Retrieved 2006.
• 2、 -. "Compositions and methods for skin conditioning". Page/Page column 21. . Retrieved 2016/02/26.
• 3、 Zhanibekov,Naubeev,Uteniyazov,Bobakulov, Kh. M.,Abdullaev. "Triterpene glycosides from astragalus. Structure of cyclolehmanoside C from A. lehmannianus". . p. 475 - 477. Retrieved 2013/09/02.