gracillin

Base Information

• Chemical Name: gracillin
• CAS No.: 19083-00-2
• Molecular Formula: C₄₅H₇₂O₁₇
• Molecular Weight: 885.056
• Hs Code.: 29329990
• European Community (EC) Number: 866-820-3
• NSC Number: 698787
• ChEMBL ID: CHEMBL1965564
• Mol file: 19083-00-2.mol

Synonyms:25(R)-Diosgenin 3-O-b-D-glucopyranosyl-(1?;3)-[a-L-rhamnopyranosyl-(1?;Diosgenin3-O-(a-L-rhamnopyranosyl(1?;2)-[b-D-glucopyranosyl(1?;3)])-b-D-glucopyranoside;Diosgenin 3-O-b-gracillimatrioside;Dulcamarin C;Gracilline;Gracillin(6CI,7CI,8CI);Lilioglycoside G;NSC 698787;Gracillin;

Chemical Property of gracillin

Chemical Property:

• Melting Point: 290-293 oC (dec.)
• Refractive Index: 1.622
• Boiling Point: °Cat760mmHg
• PKA: 12.78±0.70(Predicted)
• Flash Point: °C
• PSA: 255.91000
• Density: 1.42g/cm³
• LogP: 0.21410
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 8
• Exact Mass: 884.47695082
• Heavy Atom Count: 62
• Complexity: 1620

Purity/Quality:

Gracillin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)OC1
• Isomeric SMILES: C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)OC1
• Description: Gracillin is a steroidal saponin that has been found in C. speciosus and has diverse biological activities. It reduces cell growth in a panel of 58 leukemia, non-small cell lung, colon, CNS, prostate, melanoma, ovarian, renal, and breast cancer cell lines (GI50s = 0.58-2.44 μM). Gracillin reduces growth of fish Ich parasite (I. multifiliis) theronts (EC50 = 0.53 mg/L) and induces 100 and 92.5% mortality of I. multifiliis protomonts and encysted tomonts, respectively, when used at a concentration of 0.8 mg/L. It decreases the number of I. multifiliis-infected goldfish by approximately 75% when used at a concentration of 1 mg/L in tank water. Gracillin (100 mg/kg) reduces ear edema induced by arachidonic acid in mice.
• Uses: Gracillin is a steroidal glycoside from the rhizomes of the family Dioscoreaceae with potential anti-proliferative effects.

Technology Process of gracillin

There total 15 articles about gracillin 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: 81.0%

diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-4,6-O-benzylidene-β-D-glucopyranoside → diosgenyl α-L-rhamnopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranoside (19083-00-2,88668-53-5)

Guidance literature:

diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-4,6-O-benzylidene-β-D-glucopyranoside; With acetic acid; at 70 ℃; for 2h;

With sodium methylate; In methanol; dichloromethane; at 20 ℃;

DOI:10.1016/S0008-6215(03)00004-1

Reference yield: 79.0%

diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside (211797-95-4) → diosgenyl α-L-rhamnopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranoside (19083-00-2,88668-53-5)

Guidance literature:

With acetic acid; at 70 ℃; for 2h;

DOI:10.1016/S0008-6215(97)10050-7

Reference yield:

proto-gracillin (54848-30-5) → diosgenyl α-L-rhamnopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranoside (19083-00-2,88668-53-5)

Guidance literature:

With Curvularia lunata 3.4381 1,4-α-D-glucan glucohydrolase; In phosphate buffer; at 50 ℃; for 6h; pH=4.0;

DOI:10.1016/j.tet.2007.04.076

upstream raw materials:

diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside

2,3,4,6-tetra-O-benzoylglucosyl bromide

diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside

diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Downstream raw materials:

D-Glucose

L-rhamnose

Refernces

• 1、 Zou, Chuan-Chun,Hou, Shu-Jie,Shi, Yang,Lei, Ping-Sheng,Liang, Xiao-Tian. "The synthesis of gracillin and dioscin: Two typical representatives of spirostanol glycosides". . p. 721 - 727. Retrieved 2007/10/03.
• 2、 Yahara, Shoji,Murakami, Naomi,Yamasaki, Masaki,Hamada, Toshiyuki,Kinjo, Jun-ei,Nohara, Toshihiro. "A FUROSTANOL GLUCURONIDE FROM SOLANUM LYRATUM". . p. 2748 - 2750. Retrieved 2007/10/02.