Cryptotanshinone

Base Information

• Chemical Name: Cryptotanshinone
• CAS No.: 35825-57-1
• Molecular Formula: C19H20O3
• Molecular Weight: 296.366
• Hs Code.: 29321900
• European Community (EC) Number: 633-682-9
• NSC Number: 686518
• UNII: 5E9SXT166N
• DSSTox Substance ID: DTXSID0044072
• Nikkaji Number: J865.486G
• Pharos Ligand ID: PCL66ULW9YSY
• Metabolomics Workbench ID: 144694
• ChEMBL ID: CHEMBL187460
• Mol file: 35825-57-1.mol

Synonyms:(15R)-cryptotanshinone;(R)-1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione;cryptotanshinon;cryptotanshinone;tanshinone C

Chemical Property of Cryptotanshinone

Chemical Property:

• Appearance/Colour: orange needle crystal
• Vapor Pressure: 1.31E-08mmHg at 25°C
• Melting Point: 184-185oC
• Refractive Index: 1.602
• Boiling Point: 459 °C at 760 mmHg
• Flash Point: 203.4 °C
• PSA: 43.37000
• Density: 1.23 g/cm³
• LogP: 3.44330
• Storage Temp.: Store at RT
• Solubility.: DMSO: ≥5mg/mL
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 296.14124450
• Heavy Atom Count: 22
• Complexity: 571

Purity/Quality:

99% ^*data from raw suppliers

Cryptotanshinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 25-50/53
• Safety Statements: 45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)C
• Isomeric SMILES: C[C@H]1COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)C
• Uses: inhibits angiogenesis Cryptotanshinone (CPT), a lipophilic diterpene derived from the roots of Salvia miltiorrhiza Bge and Salvia przewalskii Maxim, may be used to study its multiple bioactivities as an antibacterial, antidermatophytic, antioxidant, anti-inflammatory and anticancer agent. Cryptotanshinone may also be studied as a differentiation factor.

Technology Process of Cryptotanshinone

There total 14 articles about Cryptotanshinone 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: 100.0%

5,6,7,8-tetrahydro-3-hydroxy-2-[(1R)-2-hydroxy-1-methylethyl]-8,8-dimethyl-1,4-phenanthrenedione (109664-02-0) → Cryptotanshinone (35825-57-1,4733-35-1)

Guidance literature:

With sulfuric acid; In ethanol; at 25 ℃; for 0.75h;

DOI:10.1021/jo00131a006

Reference yield: 50.0%

1,6,6-trimethyl-1,2,6,7,8,9-hexahydro-phenanthro[1,2-b]furan-10-ylamine (534573-58-5) → (+/-)-cryptotanshinone (17545-07-2,35825-57-1,4733-35-1)

Guidance literature:

With sodium dihydrogenphosphate; potassiuim nitrosodisulfonate;

DOI:10.1016/S0040-4039(03)00191-6

Reference yield:

→ (+/-)-cryptotanshinone (17545-07-2,35825-57-1,4733-35-1)

Guidance literature:

DOI:10.1246/bcsj.34.895 DOI:10.1246/bcsj.42.3318

upstream raw materials:

1,6,6-trimethyl-1,2,6,7,8,9-hexahydro-phenanthro[1,2-b]furan-10-ylamine

5,6,7,8-tetrahydro-3-hydroxy-2-[(1R)-2-hydroxy-1-methylethyl]-8,8-dimethyl-1,4-phenanthrenedione

1-bromo-4-methylpent-3-ene

2-bromoanisole

Downstream raw materials:

tanshinone-IIA

5,6,7,8-tetrahydro-3-hydroxy-2-[(1R)-2-hydroxy-1-methylethyl]-8,8-dimethyl-1,4-phenanthrenedione

(R)-4,9,9-trimethyl-4,5,9,10,11,12-hexahydrofuro[3,2-c]naphtho[2,1-e]oxepine-1,3-dione

(R)-2-(1-(ethoxycarbonyl)-5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-methyl-4,5-dihydrofuran-3-carboxylic acid

Refernces

• 1、 Jiang, Ying-Yan,Li, Qian,Lu, Wei,Cai, Jun-Chao. "Facile and efficient total synthesis of (±)-cryptotanshinone and tanshinone IIA". . p. 2073 - 2075. Retrieved 2007/10/03.