Decursin

Base Information

• Chemical Name: Decursin
• CAS No.: 5928-25-6
• Molecular Formula: C₁₉H₂₀O₅
• Molecular Weight: 328.365
• Hs Code.: 29322090
• UNII: E95RTO3YQR
• DSSTox Substance ID: DTXSID90974706
• Nikkaji Number: J14.116J
• Wikidata: Q27106347
• Metabolomics Workbench ID: 69146
• ChEMBL ID: CHEMBL481658
• Mol file: 5928-25-6.mol

Synonyms:2-butenoic acid, 2-methyl-, (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo(1,2-b:5,4-b')dipyran-7-yl ester, (2Z)-;2H,6H-benzo(1,2-b:5,4-b')dipyran-2-one, 7,8-dihydro-7-hydroxy-8,8-dimethyl-, (S)-;decursin;decursinol;decursinol angelate

Chemical Property of Decursin

Chemical Property:

• Vapor Pressure: 5.54E-09mmHg at 25°C
• Melting Point: 93-94℃
• Refractive Index: 1.58
• Boiling Point: 469.4 °C at 760 mmHg
• Flash Point: 206.6 °C
• PSA: 65.74000
• Density: 1.24 g/cm³
• LogP: 3.38450
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble5mg/mL, clear
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 328.13107373
• Heavy Atom Count: 24
• Complexity: 585

Purity/Quality:

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

Decursinol angelate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)OC1CC2=C(C=C3C(=C2)C=CC(=O)O3)OC1(C)C)C
• Isomeric SMILES: CC(=CC(=O)O[C@H]1CC2=C(C=C3C(=C2)C=CC(=O)O3)OC1(C)C)C
• Description: Decursin is a phytochemical originally isolated from A. gigas with diverse biological activities. It reduces the growth of B16/F10 murine melanoma cells, but not NIH-3T3 fibroblasts, via induction of apoptosis and increased caspase-3 activity when used at concentrations ranging from 40 to 100 μM. In vivo, decursin (10 mg/kg, i.p.) reduces tumor growth in a B16/F10 mouse xenograft model. Decursin inhibits RANKL-induced osteoclast differentiation and decreases fusion and migrations of pre-osteoclasts in vitro and prevents LPS-induced bone erosion in mice. In a mouse model of seizures induced by kainic acid , decursin (20 mg/kg) increases latency to the first electroencephalographic (EEG) discharge and attenuates the intensity and reduces the frequency of seizure discharges in the parietal cortex. Decursin inhibits tube formation and expression of VEGF receptor 2 (VEGFR2) in human retinal microvascular endothelial cells (HRMECs) and human umbilical vein endothelial cells (HUVECs) in vitro and reduces retinal expression of VEGFR2 and neovascularization in rats with diabetes induced by streptozotocin . It also reduces hepatic collagen expression, serum levels of ALT, AST, and ALP, and production of reactive oxygen species (ROS) in a mouse model of CCL4-induced liver fibrosis.
• Uses: Decursin is a bioactive metabolites from the root of Angelica gigas Nakai which exhibits neuro-protective and cognitive enhancement effects. Human monoamine oxidase (MAO) inhibitor. Also, it could be useful for the treatment of bone associated with excessive bone resorption.

Technology Process of Decursin

There total 31 articles about Decursin 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: 92.0%

3,3-Dimethylacryloyl chloride (3350-78-5) + decursinol (5993-18-0,15575-65-2,21860-31-1,23458-02-8) → decursin (25245-91-4,33261-71-1,63100-57-2,5928-25-6)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(01)00642-6

Reference yield: 75.0%

3,3-Dimethylacryloyl chloride (3350-78-5) + decursinol (5993-18-0,15575-65-2,21860-31-1,23458-02-8) → 2,2-dimethyl-8-oxo-2,3,4,8-tetrahydropyrano[3,2-g]chromen-3-yl 3-methylbut-2-enoate (5928-25-6,25245-91-4,33261-71-1,63100-57-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/j.bmc.2011.12.002

Reference yield: 64.0%

decursinol (5993-18-0,15575-65-2,21860-31-1,23458-02-8) + 3-Methylbutenoic acid (541-47-9) → decursin (25245-91-4,33261-71-1,63100-57-2,5928-25-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1016/j.ejmech.2010.09.006

upstream raw materials:

3,3-Dimethylacryloyl chloride

decursinol

7-hydroxy-2H-chromen-2-one

7-[(4-methoxybenzyl)oxy]-2H-chromen-2-one

Downstream raw materials:

decursinol

(-)-cis-decursidinol

decursinol

Refernces

• 1、 Lee, Kyeong,Lee, Jee-Hyun,Boovanahalli, Shanthaveerappa K.,Choi, Yongseok,Choo, Soo-Jin,Yoo, Ick-Dong,Kim, Dong Hee,Yun, Mi Young,Lee, Gye Won,Song, Gyu-Yong. "Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells". experimental part. p. 5567 - 5575. Retrieved 2011/02/22.
• 2、 -. "COMPOSITION COMPRISING DECURSIN DERIVATIVE FOR TREATING AND PREVENTING ATOPIC DERMATITIS". Page/Page column 17-18. . Retrieved 2008/12/08.