Marmin

Base Information

• Chemical Name: Marmin
• CAS No.: 14957-38-1
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.397
• DSSTox Substance ID: DTXSID001318442
• Nikkaji Number: J15.291I
• Wikidata: Q104389968
• Metabolomics Workbench ID: 121505
• ChEMBL ID: CHEMBL1078441
• Mol file: 14957-38-1.mol

Synonyms:7-(6',7'-dihydroxygeranyloxy)coumarin;marmin

Chemical Property of Marmin

Chemical Property:

• Vapor Pressure: 3.81E-12mmHg at 25°C
• Melting Point: 123-124 °C
• Boiling Point: 531.9°Cat760mmHg
• PKA: 14.65±0.29(Predicted)
• Flash Point: 188.8°C
• PSA: 79.90000
• Density: 1.193g/cm³
• LogP: 3.03010
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 332.16237386
• Heavy Atom Count: 24
• Complexity: 494

Purity/Quality:

98%Min ^*data from raw suppliers

Marmin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCOC1=CC2=C(C=C1)C=CC(=O)O2)CCC(C(C)(C)O)O
• Isomeric SMILES: C/C(=C\COC1=CC2=C(C=C1)C=CC(=O)O2)/CC[C@H](C(C)(C)O)O

Technology Process of Marmin

There total 16 articles about Marmin 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: 96.0%

Epoxyaurapten (21499-17-2) → (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine (5980-09-6,14957-38-1,31946-96-0,32064-13-4,61347-54-4,130548-21-9)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85097-3

Reference yield:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine (5980-09-6,14957-38-1,31946-96-0,32064-13-4,61347-54-4,130548-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / m-CPBA; K₂CO₃ / CH₂Cl₂ / 24 h / 0 °C

2: 10 percent / NaH / dimethylformamide / 12 h / 20 °C

3: Rhodococcus ruber DSM 43338 / H₂O; various solvent(s) / 216 h / pH 8.0

With Rhodococcus ruber DSM 43338; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2003.10.106

Reference yield:

(R)-6-O-(4-geranyloxy-2-hydroxy)cinnamoylmarmin (142628-36-2) → (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine (5980-09-6,14957-38-1,31946-96-0,32064-13-4,61347-54-4,130548-21-9)

Guidance literature:

With sodium hydroxide; In methanol; at 23 ℃; for 3h;

DOI:10.1016/0031-9422(92)80291-L

upstream raw materials:

auraptene

Epoxyaurapten

(R)-6-O-(4-geranyloxy-2-hydroxy)cinnamoylmarmin

(E)-7-<<5-(3,3-dimethyloxiranyl)-3-methyl-2-pentenyl>oxy>-2H-1-benzopyran-2-one

Refernces

• 1、 Ohashi, Kazuyoshi,Watanabe, Hisashi,Ohi, Katsuhide,Arimoto, Hirokazu,Okumura, Yasuaki. "Two New 7-Geranyloxycoumarins from the Bark of Aegle Marmelos, an Indonesian Medicinal Plant". . p. 881 - 882. Retrieved 2007/10/03.
• 2、 Zhang,Archelas,Meou,Furstoss. "Microbiological transformations. 21. An expedient route to both enantiomers of marmin and epoxyauraptens via microbiological dihydroxylation of 7-geranyloxycoumarin". . p. 247 - 250. Retrieved 2007/10/02.