Cucurbitacin I

Base Information

• Chemical Name: Cucurbitacin I
• CAS No.: 2222-07-3
• Molecular Formula: C30H42O7
• Molecular Weight: 514.659
• European Community (EC) Number: 218-736-8
• UNII: SHQ47990PH
• ChEMBL ID: CHEMBL387737
• DSSTox Substance ID: DTXSID501015546
• Metabolomics Workbench ID: 34415
• Nikkaji Number: J7.369E
• NSC Number: 521777,112167
• Pharos Ligand ID: LDRHDYTD7P2Y
• Wikidata: Q27106265
• Mol file: 2222-07-3.mol

Synonyms:cucurbitacin I;elatericin B;JSI 124;JSI124

Chemical Property of Cucurbitacin I

Chemical Property:

• Vapor Pressure: 1.5E-22mmHg at 25°C
• Melting Point: 148-150°C
• Refractive Index: 1.593
• Boiling Point: 716.9 °C at 760 mmHg
• PKA: 8.51±0.70(Predicted)
• Flash Point: 401.3 °C
• PSA: 132.13000
• Density: 1.26 g/cm³
• LogP: 3.61940
• Storage Temp.: −20°C
• Solubility.: ≥22.45 mg/mL in DMSO; insoluble in EtOH; ≥51.2 mg/mL in H2O with ultrasonic
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 514.29305367
• Heavy Atom Count: 37
• Complexity: 1160

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cucurbitacin I ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XiT+
• Hazard Codes: Xi,T+
• Statements: 25-28
• Safety Statements: 1-22-45-36/37-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2C=C(C1=O)O)C)C)C(C)(C(=O)C=CC(C)(C)O)O)O)C)C
• Isomeric SMILES: C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O)C)C)[C@](C)(C(=O)/C=C/C(C)(C)O)O)O

Technology Process of Cucurbitacin I

There total 6 articles about Cucurbitacin I 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: 96.8%

cucurbitacin E (18444-66-1) → cucurbitacin I (2222-07-3)

Guidance literature:

With lithium hydroxide; In methanol; water; at 20 ℃; for 2h;

Reference yield: 38.0%

cucurbitacin D (3877-86-9) → cucurbitacin I (2222-07-3)

Guidance literature:

With bromobenzene; N,N-dimethyl acetamide; sodium acetate; palladium diacetate; at 80 ℃; for 24h; Sealed tube;

DOI:10.1021/acs.jnatprod.5b00054

Reference yield: 35.0%

cucurbitacin I 2-O-β-D-glucopyranoside (16307-33-8,26260-47-9) → cucurbitacin I (2222-07-3)

Guidance literature:

With β-glucosidase enzyme; water; at 37 ℃; for 72h; pH=5; Enzymatic reaction; acetate buffer;

upstream raw materials:

cucurbitacin I 2-O-β-D-glucopyranoside

cucurbitacin E

cucurbitacin D

Refernces

• 1、 Hall, Jessica A.,Seedarala, Sahithi,Rice, Nichole,Kopel, Lucas,Halaweish, Fathi,Blagg, Brian S. J.. "Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery". . p. 873 - 879. Retrieved 2015/05/13.
• 2、 -. "CUCURBITACIN COMPOUNDS". Page/Page column 7-8. . Retrieved 2008/06/13.