kaji-ichigoside F1

Base Information

• Chemical Name: kaji-ichigoside F1
• CAS No.: 95298-47-8
• Molecular Formula: C36H58O10
• Molecular Weight: 650.851
• ChEMBL ID: CHEMBL4128666
• DSSTox Substance ID: DTXSID201316292
• Nikkaji Number: J440.562E
• Wikidata: Q105166788
• Mol file: 95298-47-8.mol

Synonyms:kaji-ichigoside F1;Kajiichigoside F1;95298-47-8;KajiichigosideF1;[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,10S,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate;CHEMBL4128666;DTXSID201316292;HY-N2297;AKOS037515255;MS-30964;CS-0019624

Chemical Property of kaji-ichigoside F1

Chemical Property:

• Melting Point: 230-232 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• Boiling Point: 741.5±60.0 °C(Predicted)
• PKA: 12.52±0.70(Predicted)
• PSA: 177.14000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 2.43370
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 650.40299804
• Heavy Atom Count: 46
• Complexity: 1250

Purity/Quality:

≥96% ^*data from raw suppliers

Kajiichigoside F1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C)O)O)C)C)C2C1(C)O)C)C(=O)OC6C(C(C(C(O6)CO)O)O)O
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(C[C@H]([C@H](C5(C)C)O)O)C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• Uses: Kajiichigoside F1 is a triterpenoid isolated from the root of Rosa laevigata. An antibacterial and a cytotoxic triterpenoid.

Technology Process of kaji-ichigoside F1

There total 3 articles about kaji-ichigoside F1 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: 68.2%

2α,19α-dihydroxy-5α,9α-urs-12-en-3-one-28-oic acid-28-O-β-D-glucopyranosyl ester (1309589-79-4) → tormentic acid (53155-25-2,119725-19-8,13850-16-3) + rosamultin (95298-47-8,146356-82-3,88515-58-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;

DOI:10.1016/j.phytochem.2014.03.002

Reference yield: 4.54%

Oleanolic acid (508-02-1) + D-glucose → androseptoside A (3391-81-9,15596-19-7,25329-81-1,77537-93-0,3391-80-8) + 28-O-β-D-glucopyranosyl oleanolate (14162-53-9) + 2α,3α,19α-trihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranosyl ester (95298-47-8) + rosamultin (95298-47-8,146356-82-3,88515-58-6) + 3-O-β-D-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside + 2α,3β,19α-trihydroxy-oleanolic acid-28-O-β-D-glucopyranoside (31297-79-7)

Guidance literature:

With Alternaria longipes AS 3.2875; potato; for 96h; regioselective reaction; Microbiological reaction;

DOI:10.1080/10286020.2010.547028

Reference yield: 4.54%

Oleanolic acid (508-02-1) + D-glucose → androseptoside A (3391-81-9,15596-19-7,25329-81-1,77537-93-0,3391-80-8) + 28-O-β-D-glucopyranosyl oleanolate (14162-53-9) + 2α,3α,19α-trihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranosyl ester (95298-47-8) + rosamultin (95298-47-8,146356-82-3,88515-58-6) + 3-O-β-D-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside + 2α,3β,19α-trihydroxy-oleanolic acid-28-O-β-D-glucopyranoside (31297-79-7)

Guidance literature:

With Alternaria longipes AS 3.2875; potato; for 96h; regioselective reaction; Microbiological reaction;

DOI:10.1080/10286020.2010.547028

upstream raw materials:

Oleanolic acid

2α,19α-dihydroxy-5α,9α-urs-12-en-3-one-28-oic acid-28-O-β-D-glucopyranosyl ester

Downstream raw materials:

euscaphic acid

Refernces

• 1、 Liu, Dai-Lin,Liu, Ying,Qiu, Feng,Gao, Ying,Zhang, Jing-Ze. "Biotransformation of oleanolic acid by Alternaria longipes and Penicillium adametzi". experimental part. p. 160 - 167. Retrieved 2011/04/15.