(3S,6aR,6bS,8R,8aS,9S,12aR,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol

Base Information

• Chemical Name: (3S,6aR,6bS,8R,8aS,9S,12aR,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol
• CAS No.: 53227-91-1
• Molecular Formula: C₃₀H₅₀O₄
• Molecular Weight: 474.725
• DSSTox Substance ID: DTXSID90967779
• Mol file: 53227-91-1.mol

Synonyms:Camelliagenin A;Olean-12-ene-3,16,22,28-tetrol;theasapogenol D;C30H5O4;C30-H5-O4;DTXSID90967779;CHEBI:176765;(3S,6aR,6bS,8R,8aS,9S,12aR,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol

Chemical Property of (3S,6aR,6bS,8R,8aS,9S,12aR,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol

Chemical Property:

• Vapor Pressure: 5.7E-16mmHg at 25°C
• Melting Point: 290 °C (light petroleum)
• Boiling Point: 582°Cat760mmHg
• Flash Point: 238.7°C
• PSA: 80.92000
• Density: 1.14g/cm³
• LogP: 5.08290
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 474.37091007
• Heavy Atom Count: 34
• Complexity: 877

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CC(C2(C(C1)O)CO)O)C)C)(C)C)O)C)C
• Isomeric SMILES: C[C@]12CC[C@@H](C(C1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@@H]4CC(C[C@@H]5O)(C)C)CO)O)C)C)(C)C)O

Technology Process of (3S,6aR,6bS,8R,8aS,9S,12aR,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol

There total 3 articles about (3S,6aR,6bS,8R,8aS,9S,12aR,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-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:

22-O-angeloylcamelliagenin A 3-O-[β-D-galactopyranosyl(1->2)][α-L-rhamnopyranosyl(1->2)-β-D-galactopyranosyl(1->3)]-β-D-glucuronopyranoside → D-Galactose (10257-28-0) + D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + L-rhamnose (73-34-7) + camelliagenin A (474-15-7,10410-75-0,107242-20-6,53227-91-1)

Guidance literature:

With sulfuric acid; water; In 1,4-dioxane; at 90 ℃; for 3h;

DOI:10.1248/cpb.60.752

Reference yield:

22-O-tigloylcamelliagenin A 3-O-[β-D-glucopyranosyl(1->2)][α-L-rhamnopyranosyl(1->2)-β-D-galactopyranosyl(1->3)]-β-D-glucuronopyranoside → D-Glucose (2280-44-6) + D-Galactose (10257-28-0) + D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + L-rhamnose (73-34-7) + camelliagenin A (474-15-7,10410-75-0,107242-20-6,53227-91-1)

Guidance literature:

With sulfuric acid; water; In 1,4-dioxane; at 90 ℃; for 3h;

DOI:10.1248/cpb.60.752

Reference yield:

16α,22α,28-trihydroxyolean-12-ene-3-O-[β-glucopyranosyl-(1''->2')][α-rhamnopyranosyl-(1'''->6')]-β-glucopyranoside → D-rhamnose (634-74-2,2438-80-4,3615-37-0,3615-41-6,3713-31-3,4348-84-9,5158-61-2,5624-55-5,5652-45-9,7420-19-1,7658-08-4,7658-09-5,7658-10-8,7724-73-4,10485-94-6,18546-02-6,18546-05-9,19479-17-5,32738-74-2,35867-45-9,39665-53-7,64364-07-4,75247-25-5,78684-66-9,84985-25-1,478518-52-4) + D-glucose (50-99-7) + camelliagenin A (474-15-7,10410-75-0,107242-20-6,53227-91-1)

Guidance literature:

With hydrogenchloride; water; In methanol; at 100 ℃; for 2h;

DOI:10.3998/ark.5550190.0012.214

Refernces

• 1、 Manguro, Lawrence Onyango A.,Midiwo, Jacob O.,Tietze, Lutz F.,Hao, Pang. "Triterpene saponins of Maesa lanceolata leaves". experimental part. p. 172 - 198. Retrieved 2011/06/09.