[(1R,2S,4S,5R,6R,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate

Base Information

• Chemical Name: [(1R,2S,4S,5R,6R,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate
• CAS No.: 470-37-1
• Molecular Formula: C₂₆H₃₄O₆
• Molecular Weight: 442.552
• Hs Code.: 29322090
• European Community (EC) Number: 636-927-8
• Wikipedia: Cinobufagin
• Mol file: 470-37-1.mol

Synonyms:470-37-1

Chemical Property of [(1R,2S,4S,5R,6R,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 133 °C(lit.)
• Refractive Index: 1.595
• Boiling Point: 595.4 °C at 760 mmHg
• PKA: 15.10±0.70(Predicted)
• Flash Point: 199.4 °C
• PSA: 89.27000
• Density: 1.29 g/cm³
• LogP: 3.79990
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 442.23553880
• Heavy Atom Count: 32
• Complexity: 923

Purity/Quality:

≥98% ^*data from raw suppliers

Cinobufagin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, T+, Xn
• Hazard Codes: Xi,T+,Xn
• Statements: 36/37/38-26/27/28-42/43-20/22
• Safety Statements: 26-36-45-36/37/39-22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1C(C2(CCC3C(C24C1O4)CCC5C3(CCC(C5)O)C)C)C6=COC(=O)C=C6
• Isomeric SMILES: CC(=O)O[C@@H]1[C@@H]([C@]2(CC[C@H]3[C@H]([C@@]24[C@H]1O4)CC[C@H]5[C@@]3(CC[C@@H](C5)O)C)C)C6=COC(=O)C=C6
• Description: Cinobufagin is a cardiotoxic bufanolide steroid secreted by the Asiatic toad Bufo gargarizans, having similar effects to digitalis and used in traditional Chinese medicine. It has potential antineoplastic activity and now is widely used in clinical practice, especially in anti-liver cancer. It has benn found to suppress cancer cell proliferation and cause apoptosis in cancer cells via a sequence of apoptotic modulators, including mitochondrial Bax and cytosolic chromosome c, and caspases 3, 8, and 9. Cinobufagin is a cardiotonic steroid that has been found in the skin of toads of genus Bufo and has diverse biological activities. It inhibits Na+/K+-ATPase activity in guinea pig heart ventricular muscle homogenates by 45% when used at a concentration of 0.3 μM. Cinobufagin is cytotoxic to HCT116 colorectal cancer cells in vitro with IC50 values of less than 50 ng/ml at 48- and 72-hour time points and induces apoptosis in a concentration-dependent manner. In vivo, cinobufagin (10 mg/kg) reduces tumor growth in an HCT116 mouse xenograft model. Cinobufagin (1 μg/ml) inhibits LPS-induced expression of MHC class II, CD80, and CD86 and release of IL-6, IL-8, TNF-α, and IL-10 in human monocyte-derived dendritic cells. It also increases expression of the antimicrobial peptides hBD2 and hBD3 in dendritic cells. Cinobufagin exhibits dose-dependent antinociceptive effects in the hot-plate, acetic acid writhing, and formalin tests in mice.
• Uses: Cinobufagine is a major component of cinobufacini (huachansu), is an important cardenolidal steroid. Cinobufagine was shown to exhibit potent anti-cancer effects.

Technology Process of [(1R,2S,4S,5R,6R,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate

There total 7 articles about [(1R,2S,4S,5R,6R,7R,10S,11S,14S,16R)-14-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate 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: 26.0%

16β-acetoxy-14β,15-epoxy-3-oxobufa-4,20,22-trienolide (6869-70-1) → 5α-cinobufagin (74532-04-0) + 3α-hydroxycinobufagin (470-37-1,74532-04-0,36121-84-3)

Guidance literature:

With sodium tetrahydroborate; In pyridine; for 6h;

Reference yield:

cinobufagin (470-37-1,36121-84-3,74532-04-0) → 3α-hydroxycinobufagin (470-37-1,74532-04-0,36121-84-3)

Guidance literature:

cinobufagin; In dichloromethane; at 20 ℃; for 2h;

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1039/c7ra11979h

Reference yield:

3-oxo-cinobufagin (6869-66-5) → 3α-hydroxycinobufagin (470-37-1,74532-04-0,36121-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 4 h / Heating

2: 26 percent / NaBH₄ / pyridine / 6 h

With sodium tetrahydroborate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; pyridine;

upstream raw materials:

16β-acetoxy-14β,15-epoxy-3-oxobufa-4,20,22-trienolide

3-oxo-cinobufagin

cinobufagin

Downstream raw materials:

cinobufagin 3-hemiglutarate p-nitrophenyl ester

cinobufagin 3-acetate

3α-hydroxycinobufagin

cinobufagin 3-succinate