Calendulaglycoside F

Base Information

• Chemical Name: Calendulaglycoside F
• CAS No.: 26020-14-4
• Molecular Formula: C₃₆H₅₆O₉
• Molecular Weight: 632.835
• Wikidata: Q105120478
• Mol file: 26020-14-4.mol

Synonyms:monoglucuronide F;oleanolic acid 3-O-glucuronide;oleanolic acid 3-O-monoglucuronide;oleanolic acid 3-O-monoglucuronide, (beta-D)-isomer

Chemical Property of Calendulaglycoside F

Chemical Property:

• Melting Point: 243-245 °C (decomp)
• Boiling Point: 750.8±60.0 °C(Predicted)
• PKA: 2.82±0.70(Predicted)
• PSA: 153.75000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 5.15010
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 632.39243336
• Heavy Atom Count: 45
• Complexity: 1260

Purity/Quality:

99.0% ^*data from raw suppliers

OleanolicAcid3-O-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)O)C)C)C2C1)C)C(=O)O)C
• Uses: Oleanolic Acid 3-O-Glucuronide exhibits hypoglycemic activities by suppressing the transfer of glucose from the stomach to the small intestine and by inhibiting glucose transport at the brush border of the small intestine in oral glucose-loaded rats.

Technology Process of Calendulaglycoside F

There total 9 articles about Calendulaglycoside F 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: 31.0%

momordin Id → 28-desglucosylchikusetsusaponin IVa (26020-14-4,108322-31-2) + oleanolic acid (508-02-1,6880-10-0,25499-90-5) + momordin Ic

Guidance literature:

With sulfuric acid; at 80 ℃; for 20h;

DOI:10.1016/0031-9422(88)80773-8

Reference yield: 9.0%

momordin Ie → 28-desglucosylchikusetsusaponin IVa (26020-14-4,108322-31-2) + oleanolic acid (508-02-1,6880-10-0,25499-90-5) + momordin I

Guidance literature:

With sulfuric acid;

DOI:10.1016/0031-9422(88)80773-8

Reference yield:

(3β)-17-carboxy-28-norolean-12-en-3-yl 3'-O-(β-D-xylopyranosyl)-β-D-glucuronide (96990-18-0) → Oleanolic acid (508-02-1) + calenduloside E (26020-14-4,108322-31-2)

Guidance literature:

With sulfuric acid; at 80 ℃; for 10h;

DOI:10.1055/s-2006-958134

upstream raw materials:

3-O-{[β-D-glucopyranosyl (1->2)]-[α-L-arabinopyranosyl (1->3)]-β-D-glucuronopyranosyl}oleanolic acid

chikusetsusaponin IVa

(3β)-17-carboxy-28-norolean-12-en-3-yl 3'-O-(β-D-xylopyranosyl)-β-D-glucuronide

saponin-C methylester

Downstream raw materials:

D-glucuronic acid

Oleanolic acid

androseptoside A

D-glucuronic acid

Refernces

• 1、 Shao, Chun-Jie,Kasai, Ryoji,Xu, Jing-Da,Tanaka, Osamu. "SAPONINS FROM ROOTS OF KALOPANAX SEPTEMLOBUS (THUNB.) KOIDZ., CIQIU: STRUCTURES OF KALOPANAX-SAPONINS C, D, E AND F". . p. 311 - 314. Retrieved 2007/10/02.
• 2、 Borel, Christian,Gupta, Mahabir P.,Hostettmann, Kurt. "MOLLUSCICIDAL SAPONINS FROM SWARTZIA SIMPLEX". . p. 2685 - 2690. Retrieved 2007/10/02.