7-Oxodihydrokarounidiol

Base Information

• Chemical Name: 7-Oxodihydrokarounidiol
• CAS No.: 143183-47-5
• Molecular Formula: C₃₀H₄₈O₃
• Molecular Weight: 456.709
• DSSTox Substance ID: DTXSID20931766
• Nikkaji Number: J465.088C
• Wikidata: Q82907350
• Mol file: 143183-47-5.mol

Synonyms:7-oxo-DC-friedo-olean-8-ene-3 alpha,29-diol;7-oxodihydrokarounidiol

Chemical Property of 7-Oxodihydrokarounidiol

Chemical Property:

• Vapor Pressure: 7.24E-15mmHg at 25°C
• Boiling Point: 559.9°C at 760 mmHg
• Flash Point: 306.5°C
• PSA: 57.53000
• Density: 1.1g/cm³
• LogP: 6.46440
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 456.36034539
• Heavy Atom Count: 33
• Complexity: 902

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(CCC2(C1CC(=O)C3=C2CCC4(C3(CCC5(C4CC(CC5)(C)CO)C)C)C)C)O)C
• Isomeric SMILES: C[C@]12CC[C@@](C[C@H]1[C@@]3(CCC4=C([C@]3(CC2)C)C(=O)C[C@@H]5[C@@]4(CC[C@H](C5(C)C)O)C)C)(C)CO

Technology Process of 7-Oxodihydrokarounidiol

There total 2 articles about 7-Oxodihydrokarounidiol 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:

Benzoic acid (3R,4aR,6bS,8aS,11R,12aR,12bS,14bS)-11-acetoxymethyl-4,4,6b,8a,11,12b,14b-heptamethyl-6-oxo-1,2,3,4,4a,5,6,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14b-icosahydro-picen-3-yl ester → 7-oxodihydrokarounidiol (143183-47-5) + Benzoic acid (3R,4aR,6bS,8aS,11R,12aR,12bS,14bS)-11-hydroxymethyl-4,4,6b,8a,11,12b,14b-heptamethyl-6-oxo-1,2,3,4,4a,5,6,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14b-icosahydro-picen-3-yl ester

Guidance literature:

With potassium hydroxide; In methanol; for 8h; Ambient temperature;

DOI:10.1016/S0031-9422(97)00433-0

Reference yield:

7-oxo-8β-D:C-friedo-olean-9(11)-ene-3α,29-diol diacetate → 7-oxodihydrokarounidiol (143183-47-5)

Guidance literature:

With potassium hydroxide; In methanol; Ambient temperature;

DOI:10.1248/cpb.42.1101

Reference yield:

7-oxodihydrokarounidiol (143183-47-5) → bryononic acid (24480-44-2)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / Ambient temperature

2: 1.) hydrazine hydrate, 2.) KOH, 3.) Ac₂O, pyridine

3: SeO₂, AcOH / 24 h / Heating

4: 1.) Li, ethylenediamine, 2.) Ac₂O, pyridine / 1.) reflux, 2 h, 2.) RT, overnight

5: 6 mg / KOH / methanol / 4 h / Ambient temperature

6: 14 mg / CrO₃*pyridine / Ambient temperature

With pyridine; potassium hydroxide; selenium(IV) oxide; chromium trioxide-pyridine complex; acetic anhydride; lithium; hydrazine hydrate; acetic acid; ethylenediamine; In methanol;

DOI:10.1248/cpb.40.1199

Downstream raw materials:

(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylic acid

bryononic acid

bryonolol

Refernces

• 1、 Akihisa, Toshihiro,Kimura, Yumiko,Kasahara, Yoshimasa,Kumaki, Kunio,Thakur, Swapnadip,Tamura, Toshitake. "7-oxodihydrokarounidiol-3-benzoate and other triterpenes from the seeds of cucurbitaceae". . p. 1261 - 1266. Retrieved 2007/10/03.