Mellein

Base Information

• Chemical Name: Mellein
• CAS No.: 1200-93-7
• Molecular Formula: C10H10 O3
• Molecular Weight: 178.188
• DSSTox Substance ID: DTXSID60891794
• Nikkaji Number: J113.633J
• Wikipedia: Mellein
• Wikidata: Q6813065
• ChEMBL ID: CHEMBL226090
• Mol file: 1200-93-7.mol

Synonyms:mellein;ochracin

Chemical Property of Mellein

Chemical Property:

• Melting Point: 37-39 °C
• Boiling Point: 392.7±42.0 °C(Predicted)
• PKA: 9.86±0.40(Predicted)
• PSA: 46.53000
• Density: 1.252±0.06 g/cm3(Predicted)
• LogP: 1.49360
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 214

Purity/Quality:

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

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=C(C(=CC=C2)O)C(=O)O1

Technology Process of Mellein

There total 34 articles about Mellein 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%

8-hydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-isochromen-1-one (126784-47-2) → (R)-(-)-mellein (480-33-1,1200-93-7,17397-85-2,62623-84-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2006.11.068

Reference yield: 97.0%

8-methoxy-3-methyl-3,4-dihydro-1H-isochromen-1-one (16281-42-8,30407-92-2,76985-75-6) → (R)-(-)-mellein (480-33-1,1200-93-7,17397-85-2,62623-84-1)

Guidance literature:

With hydrogen bromide; acetic acid; for 4h; Heating;

DOI:10.1016/S0957-4166(97)00217-6

Reference yield: 97.0%

(R)-(-)-mellein acetate (104331-43-3) → (R)-(-)-mellein (480-33-1,1200-93-7,17397-85-2,62623-84-1)

Guidance literature:

With methanol; water; triethylamine; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96780-8

upstream raw materials:

carbon dioxide

(R)-1-(3-Methoxymethoxy-phenyl)-propan-2-ol

1-Methoxymethoxy-3-((R)-2-methoxymethoxy-propyl)-benzene

(-)-3,4-dihydro-8-hydroxy-3-methyl-7-isocoumarincarboxylic acid

Downstream raw materials:

2-hydroxy-6-methylbenzoic acid

(1R,3S)-(-)-thysanone

6-(1-propenyl)salicylic acid

Refernces

• 1、 Islam, Md. Sadequl,Ishigami, Ken,Watanabe, Hidenori. "Synthesis of (-)-mellein, (+)-ramulosin, and related natural products". . p. 1074 - 1079. Retrieved 2007.
• 2、 Clayden, Jonathan,Stimson, Christopher C.,Helliwell, Madeleine,Keenan, Martine. "Addition of lithiated tertiary aromatic amides to epoxides and aziridines: Asymmetric synthesis of (S)-(+)-mellein". . p. 873 - 876. Retrieved 2006.
• 3、 Mori, Kenji,Gupta, Ashok K.. "CHIRAL SYNTHESIS OF (R)-(-)-MELLEIN AND (3R,4aS)-(+)-RAMULOSIN". . p. 5295 - 5300. Retrieved 1985.
• 4、 Saito, Fumiyo,Kuramochi, Kouji,Nakazaki, Atsuo,Mizushina, Yoshiyuki,Sugawara, Fumio,Kobayashi, Susumu. "Synthesis and absolute configuration of (+)-pseudodeflectusin: Structural revision of aspergione B". . p. 4796 - 4799. Retrieved 2006.
• 5、 Huang, Chao,Xiong, Juan,Guan, Hui-Da,Wang, Chang-Hong,Lei, Xinsheng,Hu, Jin-Feng. "Discovery, synthesis, biological evaluation and molecular docking study of (R)-5-methylmellein and its analogs as selective monoamine oxidase A inhibitors". . p. 2027 - 2040. Retrieved 2019/04/10.