Bergamottin

Base Information

• Chemical Name: Bergamottin
• CAS No.: 7380-40-7
• Molecular Formula: C21H22O4
• Molecular Weight: 338.403
• European Community (EC) Number: 639-137-1,866-344-6
• NSC Number: 710599
• UNII: JMU611YFRB
• DSSTox Substance ID: DTXSID50897528
• Nikkaji Number: J15.428H
• Wikipedia: Bergamottin
• Wikidata: Q568006
• Pharos Ligand ID: GQCUMLS1W6LD
• Metabolomics Workbench ID: 73977
• ChEMBL ID: CHEMBL1078442
• Mol file: 7380-40-7.mol

Synonyms:5-geranoxypsoralen;8-geranyloxypsoralen;bergamottin

Chemical Property of Bergamottin

Chemical Property:

• Vapor Pressure: 2.85E-10mmHg at 25°C
• Melting Point: 75-80 °C
• Refractive Index: 1.583
• Boiling Point: 503.7 °C at 760 mmHg
• Flash Point: 258.4 °C
• PSA: 52.58000
• Density: 1.153 g/cm³
• LogP: 5.61070
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 338.15180918
• Heavy Atom Count: 25
• Complexity: 570

Purity/Quality:

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

Bergamottin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCOC1=C2C=CC(=O)OC2=CC3=C1C=CO3)C)C
• Isomeric SMILES: CC(=CCC/C(=C/COC1=C2C=CC(=O)OC2=CC3=C1C=CO3)/C)C
• Uses: Bergamottin (BG), a component of grapefruit juice, is a mechanism-based inactivator of CYP3A4 and contributes, in part, to the grapefruit juice-drug interaction.

Technology Process of Bergamottin

There total 4 articles about Bergamottin 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: 98.0%

trans-geranyl bromide (6138-90-5) + bergaptol (486-60-2) → bergamottin (7380-40-7)

Guidance literature:

With sodium hydroxide; benzyl tri-n-butylammonium bromide;

DOI:10.1016/S0960-894X(97)10043-9

Reference yield: 61.0%

trans-geranyl bromide (6138-90-5) + bergaptol (486-60-2) → C31H38O4 + bergamottin (7380-40-7)

Guidance literature:

With sodium acetate; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 70 ℃; for 16h;

Reference yield:

bergaptol (486-60-2) + geranyl diphosphate (763-10-0) → bergamottin (7380-40-7)

Guidance literature:

With CpPT₁ from nicotiana benthamiana leaves; Enzymatic reaction;

DOI:10.1073/pnas.2022294118

upstream raw materials:

trans-geranyl bromide

bergaptol

bergapten

geranyl diphosphate

Downstream raw materials:

bergaptol

Epoxybergamottin

6',7'-dihydroxybergamottin

17,18-dihydroxybergamottin

Refernces

• 1、 Munakata, Ryosuke,Olry, Alexandre,Takemura, Tomoya,Tatsumi, Kanade,Ichino, Takuji,Villard, Cloé,Kageyama, Joji,Kurata, Tetsuya,Nakayasu, Masaru,Jacob, Florence,Koeduka, Takao,Yamamoto, Hirobumi,Moriyoshi, Eiko,Matsukawa, Tetsuya,Grosjean, Jérémy,Krieger, Célia,Sugiyama, Akifumi,Mizutani, Masaharu,Bourgaud, Frédéric,Hehn, Alain,Yazaki, Kazufumi. "Parallel evolution of UbiA superfamily proteins into aromatic O-prenyltransferases in plants". . . Retrieved 2021/05/11.
• 2、 Marumoto, Shinsuke,Miyazawa, Mitsuo. "Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor". supporting information; experimental part. p. 784 - 788. Retrieved 2012/03/22.